The Budget Babe | Affordable Fashion & Style Blog

Win Cool Stuff: Sperry Top-Sider Fall/Winter Boots

And the winner is… #6 Stephanie! Congrats to our winner and thanks to everyone who participated!

Please note: This giveaway has ended and is now closed to further entries.

You've seen me wearing my Sperry Top-Sider Boots here and here, now it's your chance to rock a pair! From the brand that's got a "passion for the sea" comes a fresh new line of fall and winter boots that mix form and function for the style-conscious trendsetter.

One lucky winner will get to choose from the Women's Bayshore Tall Boot, Ladyfish Boot, Sandfish Boot, Northstar Boot, or Chatsworth Boot! (Approx. retail value of $98-$225)

To enter, leave a comment below telling us which boot you'd pick if you won and how you'd style it.

Good luck!!

Prize subject to availability. This giveaway is open to US residents only. Comments must be posted by 12 noon ET on Thursday November 25th to be eligible to win.
I'd pick the Bayshore Tall boot! I tend towards the girly, fitted, structured clothes and dresses available. This would be a good way to ground my outfits while remaining softer and not as jarring as pairing combat boots would be.
#1 Christina on 2010-11-18 18:18 (Reply)
I would love the Bayshore Tall Boot!!!
I'd pair it black skinny jeans, my Gap gray long sleeved thermal T shirt, an over sized sweater cinched at the waist with a belt. Can't forget jewelry, so I'd wear my fireball crystal studs from Aldo and a chunky ring.
#1.1 Sonal on 2010-11-18 21:36 (Reply)
I'd love to wear Ladyfish boots and style it with skinny jeans and a woollen sweater and throw on a long necklace.
#1.2 Shristi on 2010-11-25 01:23 (Reply)
Id pick the Bayshore Tall Boot in tan. Id wear with with my summer floral dresses and knit sweaters
#2 Ariana on 2010-11-18 18:22 (Reply)
Northstar boots look great
#3 Beale Street Chick (Homepage) on 2010-11-18 18:23 (Reply)
I'd wear them with shorts and black tights and a turtleneck.
#3.1 Beale Street Chick (Homepage) on 2010-11-18 18:25 (Reply)
So hard! It's tough between the Bayshore Tall Boot, and the Northstar boot. Bayshore would look so cute w/some Jeans, a turtleneck & of course a matching scarf!! Or even a jean skirt. In the Northstar, that can be worn w/anything! But I see myself in some fishnet stockings and a skirt :-)
#4 Christina (Homepage) on 2010-11-18 18:24 (Reply)
i'd pick the northstar boot - wear it with leggings and an oversized sweater or sweater/dress for something comfy and casual.
#5 emily n. on 2010-11-18 18:25 (Reply)
I would choose the Chatsworth. Every petite girl needs a heel!
#6 Stephanie on 2010-11-18 18:27 (Reply)
Living in New England and having a long walk into work I would pick the Chatsworth. Not only would they keep me warm during the cold months they are very fashionable. What more could a girl ask for?
#7 Libby on 2010-11-18 18:29 (Reply)
I would pick the Bayshore boot in Tan to go with jeggings, and a chunky knit sweater, and topped with a cute beret. LOVE.
#8 Hannah on 2010-11-18 18:29 (Reply)
The Bayshore tall boots are gorgeous and look like they'd easily become my staple winter shoe
#9 Marcy (Homepage) on 2010-11-18 18:29 (Reply)
I would pick the adorable Women's Sandfish Boot in Barley Suede. I would wear them with tucked in pants or jeans and a cute, warm sweater!
#10 Lynn on 2010-11-18 18:30 (Reply)
I think the Chatsworth boot is to die for! Classic winter white in a glam design not only looks stylish but also works as a cold weather staple. These classy wedges would jazzify any pair of jeggings combined with a long, tunic cableknit sweater and metallic hobo bag!! Tres Chic!!
#11 Tammy Humphrey (Homepage) on 2010-11-18 18:30 (Reply)
I LOVED the Ladyfish boot on you, I'd totally go with that one. Would probably style them with my fave BR skinny jeans, a green plaid cowboy-style button down and brown coat. :-)
#12 Trude (Homepage) on 2010-11-18 18:33 (Reply)
I like the easy pull on style of the Sandfish boot. I'd rock them with jeans and a sweater.
#13 Stefanie on 2010-11-18 18:33 (Reply)
I would pick the Ladyfish Boot in dark brown as shown above. I'd love to wear it with dark blue jeans, brown big belt and a white blouse.
#14 Anya (Homepage) on 2010-11-18 18:33 (Reply)
I would choose the Chatsworth boot! I would wear it with my skinny jeans, turtleneck, and furry vest. COZY!
#15 Kim H on 2010-11-18 18:34 (Reply)
I'd pick the Chatsworth boot - they look so comfy!
#16 Katie on 2010-11-18 18:38 (Reply)
Loving the bayshore tall boot. It would be perfect to wear with skinny jeans, a cozy winter sweater, and a necklace in complementary colors
#17 Sara K on 2010-11-18 18:38 (Reply)
I love the Ladyfish boot! I would wear it with skinny jeans, a cream colored sweater, and a classic trench over it all.
#18 Meghan (Homepage) on 2010-11-18 18:38 (Reply)
the bayshore tall boot is for me! i'd wear it with jeans tucked in and my blanket print coat for shopping or hanging out satudays on a cold day for a much more sophisticated look than uggs!
#19 gay on 2010-11-18 18:39 (Reply)
I would love to have the Ladyfish boot! I have trouble finding boots that are small enough in the calves, but these would work great with the laces. I would wear these with jeans and an oversized sweater, along with a scarf and floppy knit hat.
#20 Hannah W on 2010-11-18 18:42 (Reply)
I'd love the Bayshore Tall Boot. I think they would look great with an oversized fisherman sweater and jeggings.
#21 Donna on 2010-11-18 18:42 (Reply)
I love the Chatsworth boot! I would do something totally unoriginal like pair them with skinnies or leggings and a cozy sweater. Love these!
#22 Elizabeth (Homepage) on 2010-11-18 18:45 (Reply)
I'd love the Ladyfish Boot to wear with skinny jeans tucked into them and a cute thick sweater with a plaid button up sticking out of the top. And a big J.Crew necklace to make it even better.
And I'd still wear them when it gets warmer with a cute skirt!
#23 Abby on 2010-11-18 18:48 (Reply)
Sperry Top-Sider Chatsworth boot is chat worthy as the strong structure, classic metal closures and sleek sole would bring in the compliments when worn with my skinny jeans, plaid shirts, and wool peacoats! The perfect fall and winter boot, it's not just an accessory, but strong fashion foundation.
#24 Nora on 2010-11-18 18:48 (Reply)
I'd pick the Chatsworth for sure, love the fur and silver detail!
#25 Molly on 2010-11-18 18:52 (Reply)
If I won, I'd choose the Bayshore Tall Boot. Because I'm pregnant (and therefore seriously going for comfort!), I'd style it with a super-soft tee, long marled cardi, cashmere scarf, and leggings. I'd love to add this boot to my winter wardrobe!
#26 Katie (Homepage) on 2010-11-18 18:56 (Reply)
The Ladyfish boot, hands down! They'd look great with skinny jeans, a ruffly floral tunic, and a trench coat.
#27 Jaymee (Homepage) on 2010-11-18 19:00 (Reply)
I absolutely love the Ladyfish boots, in either color. They seem like such a funky twist on a traditionally "preppy" look. My first thought was that I'd pair them with skinny dark jeans, an oversized top, and some chunky jewelry. But now that I look at them more, I think they'd be really fun with opaque tights and a short skirt. Either way!
#28 Jessica on 2010-11-18 19:04 (Reply)
Chatsworth with shorts & hoodie, any length skirt, leggings & sweater.
#29 Y. Clark on 2010-11-18 19:05 (Reply)
Id wear my skinny jeans and my camel colored turtleneck alongside with a long beaded necklace. All this paired with the ever so lovely Sperry Ladyfish boot! This is a boot that Kate Middleton would go for!
#30 Michelle v. on 2010-11-18 19:16 (Reply)
I would wear the Northstar boots with tights, a cute wool miniskirt, and a chunky cable knit sweater. So cute!
#31 Rebekah (Homepage) on 2010-11-18 19:16 (Reply)
I'd want the Chatsworth Boot and pair it with dark skinny jeans and a poncho.
#32 Jeannie on 2010-11-18 19:17 (Reply)
I'd definitely go with the Bayshore boots! They look like a really comfortable go to boot that matches just about everything. Totally makes me look more forward to cold days when I normally dread them. :-P
#33 Jenny (Homepage) on 2010-11-18 19:19 (Reply)
I would love to have the Bayshore boots!!! They would look so cute with a pair of skinny jean and my oversize sweater. Or I would wear them with jean shorts with tights under it. !!!
#34 Julia on 2010-11-18 19:24 (Reply)
Bayshore! I'd try them with skinny jeans a flowy top or with a fabulous bohemian maxi dress....(with tights underneath)
#35 Megan (Homepage) on 2010-11-18 19:33 (Reply)
Enter me please...i would get the the color and it has a wedge..perfect
#36 Milly on 2010-11-18 19:47 (Reply)
What a great giveaway! I have loved both pairs of boots on you. The chatsworth boots would be wonderful to own and wear throughout the colder months!

#37 christine on 2010-11-18 19:57 (Reply)
I would def rock the ladyfish boot. The color is rich, and its the perfect blend of masculine, feminine and polish. I would wear them with skinny cargos and chunky knit ponchos, or even my chunky grey tights and babydoll dress with a hoodie and a black bomber jacket over top. I am in love with these boots
#38 Amanda (Homepage) on 2010-11-18 20:02 (Reply)
I'd have to pick the Northstar boot, of course. I love the modern take on this classic, preppy style. I hope I win so I can get a pair in brown and wear them with black leggings, a red strapless dress with a henley underneath, a brown leather belt and a wool cape to work. On the weekend I'd wear them with my super skinny 7 for all mankind jeans, an extra long tank, a brown leather moto jacket and an ivory pashmina.
#39 616girl on 2010-11-18 20:03 (Reply)
I would pick the one on bottom row far left with the shearlih and pair with dark blue jeggings and a cute flowy peasant top!
#40 Erykah on 2010-11-18 20:10 (Reply)
I'd pick the Bayshore Tall Boot - love the look! I'd wear them with jeans and a wintery sweater.
#41 chouette22 on 2010-11-18 20:11 (Reply)
I would pick the Northstar boot because I LOVE the lace detailing and its a tall boot. You can wear it with skinny jeans and a oversized sweater or be more rocker chic by wearing it with a leather jacket. This boot is very versatile and that's why I would pick this boot.
#42 Fanny on 2010-11-18 20:20 (Reply)
...give me the Ladyfish Boot (I'll need that in dark brown shearling). Please and thank you ;-)
#43 Julie on 2010-11-18 20:25 (Reply)
For me, the Ladyfish in the darker color. I think it would be cute with rolled up straight legged jeans and some fun socks. My daughter says she'd do the Northstar with leggings and a mini or shorts.
#44 Kris on 2010-11-18 20:27 (Reply)
I would definitely pick the Northstar paired with a long cozy sweater and some jeggings!
#45 Alicia on 2010-11-18 20:31 (Reply)
The Chatsworth, absolutely. I've been searching for the right black boot, but seeing these, I think off-white can be the new black, especially for me. And because I'm 6' tall, I can make a boot work with damn near anything. (Being tall ain't all sunshine and roses, so I claim my perks where I find 'em!)
#46 Sally Felt (Homepage) on 2010-11-18 20:45 (Reply)
I would choose the ladyfish boot. I love my regular Sperry slide ins having a boot similar would be amazing. I would style it with a pair of skinny jeans or jeggins with a nice cropped lether jacket and a really girl embellished top underneath.
#47 Kim on 2010-11-18 20:52 (Reply)
I love the Northstar boot! They look so comfortable and stylish! Great with my favorite skinnies and a cozy sweater.
#48 Sonia on 2010-11-18 21:06 (Reply)
Ladyfish Boot b/c they are stylish and comfy....they are unique and fancy....they are adorable and rugged....they are exactly who i am....LUV THEM!
#49 Hope on 2010-11-18 21:13 (Reply)
What a tough choice. I love the lacing of the Northstar boots, but the Chatsworth boots look soo comfy. I think I would have to go with the Chatsworth, they're beautiful, functional, and would be warm throughout the winter! Love love loveee.
#50 Megan on 2010-11-18 21:21 (Reply)
I would pick the Ladyfish Boot in brown deerskin because they have that masculine yet lady-sophisticated feel to them, with a hint of the classic Sperry. I would pair them with jeans, a large oversized sweater or a button down!
#51 Maria on 2010-11-18 21:26 (Reply)
I would pick the Bayshore tall boot, and probably style it casually with jeans, an oversized men's shirt cinched with a belt, and then something a little glittery to liven it up (perhaps a shiny leather belt or some fabulous necklaces)
#52 Claire on 2010-11-18 21:55 (Reply)
I'd pick the Sandfish boot in brown, and wear it in winter with jeans and a peacoat, and in spring/summer with a floral dress or skirt. They are so versatile and gorgeous!
#53 anja on 2010-11-18 21:59 (Reply)
I like the Sandfish Boot! It would be so great this winter.
#54 brandi (Homepage) on 2010-11-18 21:59 (Reply)
I would pick the Chatsworth. They are like Uggs but way better since you can make it through all types of weather in the Chatsworth and they have such better detailing. I would wear my usually outfit of leggings, sweater dress and a big scarf!
#55 Christina on 2010-11-18 22:01 (Reply)
I love the Northstar boot and style it just like the ad -with a toggle coat and nautical stripe shirt.
#56 Audrey on 2010-11-18 22:02 (Reply)
I would definitely pick the Ladyfish Boot. For one, its sooo cute! I can wear it with skinny jeans & also pair it up with cute sweater dresses. Secondly, I have huge calves and the tall boots will not fit. LOL! Thanks for an awesome giveaway!
#57 Kfloveinme on 2010-11-18 22:04 (Reply)
The Bayshore Tall Boot, I'd pair it with skinny jeans and a great coat. :-) I never thought Sperry Top Sider would have such great boots. They look so comfortable.
#58 Emily on 2010-11-18 22:05 (Reply)
I would definitely get the Bayshore Tall Boot!! It looks comfy and warm with a supportive and sturdy sole. It would look adorable with a chunky knit sweater and skinny jeans!
#59 Evan on 2010-11-18 22:09 (Reply)
The Bayshore Tall boot is beautiful! I would style the tan version with an airy, light dress in a cream toward peach color. Chunky black cardigan or sweater, black knee-high socks on sheer tights. Some layered necklaces and a skinny belt finish the look!
#60 Azalea on 2010-11-18 22:18 (Reply)
The ladyfish in dark brown! Skinny jeans or leggings with a loose tee or sweater and a scarf. So cute.
#61 Melissa on 2010-11-18 22:27 (Reply)
I loved the Ladyfish Boot on you! It definitely looks great with skinny jeans. Thanks for the giveaway!
#62 hroussi on 2010-11-18 22:27 (Reply)
The Chatsworth boots are gorgeous, and definitely the ones I would pick. I would wear them with velvet leggings and a flowy, girly pink dress. Thanks for the giveaway!
#63 Amy on 2010-11-18 22:30 (Reply)
I'd definitely pick the Northstar boot! Not only are they cute and fashionable but they look comfortable too! I would wear these with a pair of jeans and an a loose top or with some tights or leggings and a oversized sweater! I'd accesorize with a cute beanie! I think these would look great with a coat as well! :-)
#64 Amrita on 2010-11-18 22:34 (Reply)
First, I must tip my hat to Sperry. These boots are right on track with the current trends: masculine boots, military lace-ups, and sexy wedges. If I had to choose, I would have to select the Brown Deerskin Ladyfish Boot, paired with a cream or beige chunky oversize, off the shoulder knit sweater (for a touch of femininity to balance the masculine feel of the boots), a red or hunter green tank top (to bring out the colors in the tongue of the boots), dark skinny jeans (for casual Fridays at work or a group date) or green skinny cargos (lunch with girlfriends or running errands), my huge yellow hobo bag (for a splash of color), my boyfriend watch (matching the robust feel of the boots) and pearl earrings (a hint of softness).
#65 Terah Shelton on 2010-11-18 22:41 (Reply)
First, I LOVE Sperry anything. It reminds me of my oh-so-preppy youth when I only wore the original top-sider. Ok, so I wore tretorns too. But the top-sider was the boat shoe that worked well on dry land too.

So, while I am madly in love with all options, I would pick the Chatsworth. They would dress up my Nebraska cold-weather wear as well as style me sassy for walking the streets of the Big Apple. Whether jeans, leggings or skirts, I'm not sure I'd take them off til spring. :-)
#66 Robin (Homepage) on 2010-11-18 22:44 (Reply)
Ohh--I would pick the Bayshore Tall Boot. They would look great with jeggings and chunky sweaters--my go to in the winter. Great giveaway!!!
#67 Amanda Cotcher on 2010-11-18 22:46 (Reply)
The Sperry Chatsworth looks like the perfect winter boot! I'd pair them with slim-fitting jeans, a cozy sweater, maybe a faux fur vest (a la MK Olsen) if I'm feeling adventurous, and a slouchy knit beanie.
#68 Joan on 2010-11-18 22:51 (Reply)
Definitely the Bayshore Tall boot. Looks so warm and comfy. Perfect for the upcoming Winter months! I would pair it with some leggings and a chunky sweater.
#69 Samantha Bender (Homepage) on 2010-11-18 22:59 (Reply)
i love the Bayshore tall boot, as does everyone else! how could i blame them they r extremely cute i love the moccasian(spelling?) look its perfect for any season!
#70 Haylee on 2010-11-18 23:03 (Reply)
I would Like Ladyfish boots. They would work well for jeans and cardigans.
#71 Debbie on 2010-11-18 23:09 (Reply)
I like the Ladyfish in brown deerskin. I would wear with straight leg jeans, flannel shirts, and cardigan.
#72 Michelle Pallas on 2010-11-18 23:17 (Reply)
I would pick the Bayshore brown tall boot. I would style them with skinny jeans and a nice warm thermal for a casual look or a nice earth toned sweater dress, with an infinity scarf to switch it up.
#73 allison on 2010-11-18 23:22 (Reply)
I love the bayshore tall boot. It would be great with my skinny jeans, but even better with my skirts and tights that I attempt to wear all winter. They are so cute!
#74 laura on 2010-11-18 23:24 (Reply)
I will choose the Bayshore Tall Boot. It looks super comfy and warm. I will style it with skinny jeans and any casual tops for daily use to campus. I also can style it with my sweater dress for cute style :-D
#75 Dian on 2010-11-18 23:25 (Reply)
Ladyfish boot! Thanks for the giveaway!
#76 Kendall on 2010-11-18 23:36 (Reply)
And I'd wear it folded down with skinny jeans, an oversized sweater, and a slouchy hat to walk around central park on a chilly day.
#76.1 Kendall on 2010-11-18 23:46 (Reply)
I like the Bayshore Tall Boot in Black. It looks perfect to deal with Chicago winter thats almost here and its stylish! I'd wear it with leggings and comfy sweaters and its a color that could go with almost anything and looks super comfortable. Great boot to be walking around in the city.
#77 Amanda on 2010-11-18 23:45 (Reply)
I like the ladyfish boot. i would wear it with straight leg jeans, a flannel and a scarf!
#78 Alicia (Homepage) on 2010-11-18 23:49 (Reply)
I'd love to have the sandfish boots and pair them with skinnies and an oversized sweater.
#79 Lindy on 2010-11-19 00:05 (Reply)
Sandfish boots are all me!
#80 Reyna on 2010-11-19 00:12 (Reply)
I'd love to have the ladyfish boots! I would probably wear them with just about everything and they would be great for my upcoming trip to Munich.
#81 rlhurwi (Homepage) on 2010-11-19 00:40 (Reply)
I would definitely choose the bayshore boots! I'd pair them with some tight dark denim and my coziest sweater!
#82 Angie on 2010-11-19 00:43 (Reply)
It's hard to choose, but...
I'd probably get the Ladyfish Boot in Brown Deerskin. I would style them with the cuff folded down, green skinny cargo pants, a black asymmetrical jacket layered over a white long sleeve scoop-neck T-shirt. I would finish it with a chunky watch and hair pulled up with a few head bands intertwined in hair.
#83 sarahsosa on 2010-11-19 00:46 (Reply)
Northstar boot in brown is my pick-it would extend my creativity and I'd pair them with skinnies and tunics or with tunics and skirts or dresses alone. I see lots of versatility with these.
#84 sue on 2010-11-19 01:12 (Reply)
I'd choose the sandfish boots, and wear them with dark-rinse skinny jeans topped with a chunky-knit cowl neck sweater.
#85 Wehaf on 2010-11-19 01:14 (Reply)
I love the chatsworth! I would wear them with skinny jeans and a slim-fit flannel... My go-to look these days!
#86 Claire on 2010-11-19 01:15 (Reply)
i'd choose the bayshore tall boot or the northstar boot and pair it with black leggings/jeggings with plaid and a cross-the-body bag.
#87 M on 2010-11-19 01:15 (Reply)
I would choose the Ladyfish Boot in Barley Suede either with or without shearling. They would look great in the fall and winter with my black jacket and skinny jeans. I won't have to look all black from head to toe then! I think they would look good either up or rolled down with the tongue not really placed neatly in line. It would give a last minute throw on casual look which could look good in contrast to a nice neat top and skinny jeans. Also, I think the ones without shearling could be worn in the spring either rolled down or regularly straight up with a shirt and a pair of denim shorts.
#88 Priscilla on 2010-11-19 01:23 (Reply)
I'm SO in love with the Northstar boot and would absolutely love to win them. I'd probably pair them with a dress, some colorful tights, and a sweater, or maybe a t, scarf, and skinny jeans on more casual days. Thanks so much!
#89 Kellie (Homepage) on 2010-11-19 01:30 (Reply)
I love the ladyfish in dark brown! it would match with any color!!

#90 janet <3 on 2010-11-19 01:40 (Reply)
I'd pick the Chatsworth boot and style it with a chunky knit sweater and denim skirt. Or skinny jeans, tunic and scarf. All the boots are lovely though.
#91 Ida on 2010-11-19 01:46 (Reply)
I love the ladyfish boot you had on!
#92 Gina on 2010-11-19 02:08 (Reply)
I'd pick the Ladyfish boot in dark brown. For the colder months, I'd pair the boots with skinny jeans and a chunky knit sweater. To add some flair, I'd add a long necklace and a cute headband. For the warmer months, I'd wear the boots with a cute floral knee-length dress, and top the outfit off with a pair of over-sized sun glasses!
#93 Florence on 2010-11-19 02:11 (Reply)
Definitely the Chatsworth... they are funky yet seem versatile at the same time. Plus, I tend to stick to a lot of black, those boots would really spice things up!
#94 Sara on 2010-11-19 02:41 (Reply)
I'm loving the Northstar boots. They would look great with leggings,and a turtleneck tucked into a skirt. :-)
#95 Hanniebon on 2010-11-19 03:32 (Reply)
I'd pick the Bayshore Tall Boot!
#96 Bridget on 2010-11-19 06:39 (Reply)
I'd wear the Bayshore Tall Boot, with skinny jeans, and a nice black turtleneck. I like the classic looks.
#97 Tahrer on 2010-11-19 07:47 (Reply)
I'd pick the Bayshore boot and wear it with denim leggings and a cozy chunky knit wrap sweater.
#98 Jessica on 2010-11-19 07:52 (Reply)
If I won, I'll definitely have to pick the Chatsworth Boot!
Wear it with an oversize winter sweater, leggings, chunky beret, gloves and Im ready for the SNOW!

Fab giveaway!
#99 Anne (Homepage) on 2010-11-19 08:02 (Reply)
I would definately choose the Bayshore Tall Boot! I love them and would be perfect for winter. I'm pregnany right now, so for me the most comfortable outfit is a dress and leggings. These boots would be a perfect addition!
#100 Jennifer (Homepage) on 2010-11-19 08:13 (Reply)
The Northstar Boot in Brown...The lower part is all traditional Boat Shoe and the Upper is luxe leather lushness...perfect for all my NYC walking this Winter..Cold Feet = Sad Feet....

I'd style it with a ponte pant (nothing lie looking fancy and feeling comfy) a vintage crush velvet blazer and my fav old school New Kids On the Block tee..
#101 Patrice (Homepage) on 2010-11-19 08:14 (Reply)
OMG this is amazing! What a coincidence :-) I'd been dieing for a pair of the Ladyfish boots (in dark brown shearling 2) because of the versitility factor. I'd definitely pair them (flipped detail side down) with some cute black jeggings, a chunky long brown wool turtle neck, tanned faux leather jacket and a cute wine beret. If it got too chilly later in the day when I'm walking home from campus, I'd flip them up for extra warm and still be stylin' ;-)
#102 Tasia on 2010-11-19 08:15 (Reply)
I would love to win the Chatsworth boot! It is so difficult to find warm but fashionable boots to plow through the snow in!
#103 JJ on 2010-11-19 08:41 (Reply)
I would pick the Bayshore Tall boot. So cute! I would pair them with either some wool legging in brown or some skinny jeans. Then I'd wear my long tie cream wool sweater with short sleeves and my cream thermal with detail on the cuffs underneath. Add a cute beanie and a scarf and I'm all set!:-)
#104 Kristi on 2010-11-19 08:41 (Reply)
My choice: Ladyfish Boots (Dark Brown Suede/deerskin)

Outfit: Skinny jeans, ivory colored sweater tunic, brown waist belt, red eternity scarf. (Optional: Plaid Wool Blazer with reds and/or browns)
#105 kandee on 2010-11-19 08:48 (Reply)
Ladyfish boot! skinny jeans with a chunky sweater!
#106 Kate N. on 2010-11-19 09:03 (Reply)
Oooh, oooh, oooh definitely the Northstar boot. These are so cute! I'd have to pair them with a pair of cable knit tights and tailored shorts, topped off with a chunky turtleneck sweater!

Good luck to everyone!

Eboni Ife'
#107 Eboni Ife' (Homepage) on 2010-11-19 09:21 (Reply)
I would pick either the Lady Fish boot or the sandfish boot and would wear them with a cardigan and a button down shirt and jeans.
#108 Stephenie Ramirez on 2010-11-19 09:23 (Reply)
I'd pick the Chatsworth, looks comfy, fluffy and warm :-)
I'd pair it with a pair of skinnies, a black scoop neck, grey chunky knit sweater + my Soia & Kyo Yan Z Coat :-) Maybe a knit beret too
#109 Mellow on 2010-11-19 09:24 (Reply)
In the next two days we are getting 3-5 feet of snow in Truckee CA! I'd pair the Bayshore Tall with tights, skirt, chunky sweater, hoop/jeweled earrings and hat, just to get out the door and stay warm!
#110 Lisa on 2010-11-19 09:36 (Reply)
The Northstar in brown with leggings and a flowy comfy sweater.
#111 Jaclyn on 2010-11-19 09:50 (Reply)
I would choose the Bayshore Tall Boot. omg, I love them so much! they'd look amazing with any winter outfit!
#112 CrystalCorrin on 2010-11-19 09:50 (Reply)
I would take the Bayshore Tall boot and wear them with tights and an oversized sweater. They look so comfy!
#113 Cori on 2010-11-19 09:59 (Reply)
I have been eyeing the Chatsworth boot...but my wallet keeps giving me the stink eye : ) I would wear this so many ways, but today- I'd probably pick my skinny jeans, comfy oversized sweater cinched at the waist with a belt, and my fun silver bangles!
#114 Dana (Homepage) on 2010-11-19 10:22 (Reply)
I have been eyeing the Chatsworth boot...but my wallet keeps giving me the stink eye! I would wear this so many ways, but today- I'd probably pick my skinny jeans, comfy oversized sweater cinched at the waist with a belt, and my fun silver bangles!
#115 Dana (Homepage) on 2010-11-19 10:23 (Reply)
The Bayshore boots for sure! I love the laces and the shearling detail!
#116 Brittany on 2010-11-19 10:39 (Reply)
I would rock those Ladyfish boots! I love them. I actually had a dream about them last night (no joke!)
#117 Mary Beth (Homepage) on 2010-11-19 10:53 (Reply)
i would love to have the chatsworth boot they are so cute. i would pair them with a rich color loose fitting sweater dress preferebly a quarter sleeve sinched at the waist with a thick belt
#118 blanca (Homepage) on 2010-11-19 10:58 (Reply)
I'd choose the Chatsworth boot. I'd wear it Christmas tree hunting with my camel coat and skinny jeans!
#119 FaithJ on 2010-11-19 11:16 (Reply)
Thanks!! I loved seeing how you styled the boots! My pick would be the Chatsworth. I would wear my dark skinny jeans, gray and white check button up with a cream furry vest over it. I can see it now! Adorable!
#120 Allison M. on 2010-11-19 11:29 (Reply)
Id go with the Ladyfish Boot. the flannel-ness...LOVE IT! I'd throw it on with just about anything....jeans, yoga pants on lazy days..and just light tuck things in. Kinda like when guys where high top sneakers and tuck their jeans in bit. Sort of a "rough" look if you will!
#121 Kathleen on 2010-11-19 11:40 (Reply)
I would wear the Northshore boot. Pair it w/ all black of course!!!! Black leggings, and loose sweaters. Also, it beats those Uggs in the cold!!
#122 jennie on 2010-11-19 11:44 (Reply)
Ladyfish boot in barley suede -- I love the plaid.
#123 Laura on 2010-11-19 11:54 (Reply)
The Chadsworth boot in Almond suede is luxurious yet casual! it would be PERFECT over skinnies or leggings during the winter :-)

Look #1: My Express Skinny jeans tucked into the Chadsworth boot paired with a cream deep v-neck sweater, light gold metalic stitch houndstooth scarf, shearling cream suede gloves, amber stud earrings and a peppermint mocha!
Look #2: black Bebe quilted knee leggings tucked into the Chadsworth boot paired with a comfy distressed v-neck t and a plaid flannel button up thrown on top. Accessorize with a large studded leather hobo, a messy bun and you're out the door!

I have always wanted a pair of Sperry's but until your blog I never even knew they made boots - amazing find!
#124 Brittany on 2010-11-19 11:59 (Reply)
I would pick the Chatsworth boot! I would wear it with my cream sweaterdress and some patterned cream tights!
#125 Danielle on 2010-11-19 12:00 (Reply)
Sandfish boot for sure. I'd wear them with skinny jeans or a sweater dress.
#126 Katie on 2010-11-19 12:06 (Reply)
I'd pick the Sandfish boot and wear them with skinny jeans and a blue and white ticking stripe button down shirt. Love them!
#127 Courtney on 2010-11-19 12:13 (Reply)
I am loving the Chatsworth Boot-what a beautiful addition to any winter wardrobe! I am picturing skinny jeans or leggings and a super cozy sweater with them.
#128 AnnieL on 2010-11-19 12:20 (Reply)
I would love the Bayshore tall boot. I'd pair it with a cute floral dress, black sweater tights, boyfriend cardigan, and a belt. SO cute!
#129 Jean on 2010-11-19 12:27 (Reply)
ladyfish boot - perfect for playing around in Boston on slushy/snowy/rainy days!
#130 Kim K on 2010-11-19 12:42 (Reply)
I would pick the Bayshore Tall Boot, pair it with some Grey leggings, black shorts, a fitted flannel tee and denim jacket. Perfect winter outfit for Santa Cruz, CA!
#131 Ayla on 2010-11-19 12:54 (Reply)
I would LOVE to wear the Ladyfish Boot with a pair of dark blue skinnies, a burnt orange wool coat I recently picked up and a cream colored Irish wool scarf. Maybe some extra wooly socks too, if its really chilly. Yum!

LOVE these boots!
#132 Colleen on 2010-11-19 12:55 (Reply)
I really love & want the Ladyfish boot in brown leather. So cool. I'd sport them with skinny pants of any kind. I'd wear them every morning when we're walking our dog, too.
#133 KGP on 2010-11-19 12:55 (Reply)
The Ladyfish boot! I'd wear my cream straight-leg cords, rolled up to show the boots, and my grey cowlneck chunky sweater to really play up the preppiness! I love my Sperry Top Sider metallic original boat shoes, I wore them all summer!
#134 BethC. on 2010-11-19 12:58 (Reply)
abso-freaking-lutely the northstar boot. it's sort of a weird hybrid of prep/grunge rock chic due to the black leather lace up and boat shoe marriage, but i'd say pair this with an amazing mid-size floral print chiffon dress with maybe 3/4 or short sleeve length, some opaque complimentary color tights, and either a knit moto-style jacket (to keep the edge) or a wrap-around cardigan either cocoon style or maybe with ruffles to soften up the edge. and definitely soft, tousled locks to top it all off!
#135 kay w. (Homepage) on 2010-11-19 13:00 (Reply)
Those Northstar boots are unbelievable - punk rocker meets regatta. I'd let them be the star of my outfit - red/violet tights, belted, cowl-neck charcoal sweater that hits mid thigh, and a pendant necklace to finish it off.
#136 lacie on 2010-11-19 13:10 (Reply)
I love the Ladyfish Boot. I would probably pair it with black leggings an oversize chunky knit turtleneck and army jacket. Perfect for Tahoe weather.
#136.1 Nikki on 2010-11-19 13:36 (Reply)
I would TOTALLY go for the women's Ladyfish Boot! Loved the way you rocked em :-) I'd probably wear them with a pair of long skinny jeans, plaid shirt topped with a furry lined jacket :-) (my casual funky style)
#137 anbreen on 2010-11-19 13:38 (Reply)
I would like the Ladyfish boots. So cute and they look really comfy and warm!
#138 Patti on 2010-11-19 14:13 (Reply)
I would get the Bayshore tall boots! Love them!
#139 Valerie on 2010-11-19 14:17 (Reply)
I love the Chatsworth boots! I would totally wear them with skinny jeans and a big chunky sweater.
#140 Ginger S. on 2010-11-19 14:18 (Reply)
I just cant choose between the Bayshore Tall Boot or the Lady Fish Boot =/ EEK! LOVE both =)
#141 Dani B on 2010-11-19 14:29 (Reply)
I love the Ladyfish Boot!! I would wear it several ways--with jeans and t-shirt and sweaters for a casual rugged look, with leggings and chunky sweater dresses or with flowy dresses with a rugged leather jacket.
#142 Tiffany Hebert on 2010-11-19 14:36 (Reply)
Omg, omg, I want the Ladfish boot SO bad!!! They are such an awesome combination of practical and cute.

I would wear them with skinny jeans, a button down and my favorite chunky cardigan with elbow patches!
#143 Jessica Auxier (Homepage) on 2010-11-19 14:42 (Reply)
The Chatsworth boots would be the perfect addition to the plum colored ribbed tights and cream colored sweater dress that I'm wearing to see the Nutcracker. I would feel like a Sugar Plum Fairy in these!
#144 Adele McKeon on 2010-11-19 14:44 (Reply)
LOVE the Northstar Boots! They look comfortable and chic at the same time - I'd wear them with dark jeans and oversized sweaters and mittens. Perfect for fall/winter!
#145 Kathy on 2010-11-19 14:51 (Reply)
I am in LOVE with the Ladyfish boot in dark brown. They are perfect mix of rugged practicality and fabulous style! I would wear them with skinny cargos or jeggings paired with oversized chunky cable knit sweaters and tees...maybe even a leather bomber jacket! I need to own these boots!
#146 Angela on 2010-11-19 14:59 (Reply)
I would love to win the Ladyfish boots - i would love to pair them with a pair of black leggings or dark wash jeggings, white a red plaid button down shirt and a slouchy gold cap with accessories! When I saw you wearing them, I feel in love with them and knew I had to have them!
#147 Aleah on 2010-11-19 15:05 (Reply)
I would rock the Bayshore Tall Boats with a Natural colored Crowl Neck sweater with a pair of Denim Jeggins and a Chunky Beret to complete the sweater
#148 Cheyenne W. on 2010-11-19 15:29 (Reply)
Oh I know I should be practical and pick the warmest option but my heart is with the Northstar in black (tough decision, I live and love me a brown boot). I love how the boot is a traditional style but with a little sexy thrown in. I would wear them with a lot of things, girly short dress plus tights; skinny jeans and big sweaters; ah they would look wonderful with my flower pants!

Thanks so much for the opportunity!
#149 Jamillah on 2010-11-19 15:30 (Reply)
I loooove the ladyfish boots- I'd wear them with skinnies and a great cape!
#150 Alana (Homepage) on 2010-11-19 15:30 (Reply)
I would choose the Ladyfish boot in Brown Deerskin. I would pair it with dark skinny jeans and a very feminine silk plum or olive green blouse. To go with the look I would wear a khaki colored trench style jacket but shorter length (hip length). I'd also accessorize with gold initial chain and gold bracelets. I love the idea of incorporating a feminine look with a more rugged boot.
#151 Andrea on 2010-11-19 15:33 (Reply)
I'd choose the Chatsworth boot with some skinny jeans and a big sweater!
#152 MKerwin on 2010-11-19 15:55 (Reply)
I'd pick the Bayshore Tall boot. I'd wear them with skinny jeans or leggings with a cute top!
#153 Cynthia on 2010-11-19 16:01 (Reply)
the northstar boot in brown. i'd pair them with over-the-knee socks and layer it with a dress and military coat. i might take the horizontal laces off the sides. but otherwise, what a beautiful boot.
thanks for a great giveaway!
#154 Chelsea on 2010-11-19 16:08 (Reply)
I would choose the Ladyfish boot in Brown Deerskin (unlaced) paired with some black jeggings, tight white long sleeve screen printed t shirt, black blazer, a brown fedora hat, and a black scarf for a busy day in the city.
#155 Maurine Obi (Homepage) on 2010-11-19 16:15 (Reply)
I'd wear the brown deerskin Ladyfish boots with straight leg jeans and a slim cardigan.
#156 Courtney on 2010-11-19 16:15 (Reply)
I absolutely love the Bayshore Tall Boots! Living in Hawaii, I would pair it with a bikini and sunglasses. :-)
#157 Liane on 2010-11-19 16:19 (Reply)
I would definitely pick the Chatsworth boot! It would be so perfect for the freezing cold Chicago winters. I would pair them with jeggings, a cozy oversized sweater, and my warmest winter coat!
#158 Becky on 2010-11-19 16:21 (Reply)
I love the Chatsworth boot! Living in Chicago, I've been looking desperately for a fashionable yet functional winter boot that will keep my feet warm and dry and this one does the trick! Love that they work with both brown and black clothes. I would sport mine with some leggings, an oversized sweater and obviously my ankle length down coat from Zara! :-)
#159 Nicole on 2010-11-19 16:38 (Reply)
i would pick the ladyfish boots. some leggings and big sweater and i would be ready for the snow!
rwvanvoorhis at gmail dot com
#160 rwvanvoorhis on 2010-11-19 16:43 (Reply)
This is hard choice between the ladyfish and the northstr boots, but I would choose the Northstar in teh end - they're so versatile!
#161 Colleen on 2010-11-19 16:47 (Reply)
Definitely the Chatsworth! I'd style it with dark skinny jeans, a cream long sleeve knit tee and a faux fur vest!
#162 Maria on 2010-11-19 16:47 (Reply)
I absolutely love the Ladyfish. I would wear them with some skinnies, a great warm flannel shirt, and an awesome jacket. Upscale rugged!
#163 Rahila Ahmed on 2010-11-19 17:14 (Reply)
I love the chatsworth ....
Id wear it with dark skinnies or dark leggings.
#164 alex on 2010-11-19 17:35 (Reply)
The Bayshore Tall Boot, with its moccasin-inspired details is perfect for a chilly, dry day. I'd rock those fabulous boots with my skinny dark-washed jeans, cream cotton tunic, chunky amber necklace and cozy Aztec-patterned swing sweater.
#165 madi on 2010-11-19 17:40 (Reply)
I love the Ladyfisher!
#166 Lauren on 2010-11-19 17:42 (Reply)
I LOVE LOVE LOVE the Chatsworth! I'd wear it with a pretty winter white sweater dress!
#167 Monica on 2010-11-19 17:57 (Reply)
The Chatsworth boot would be perfect with dark skinny jeans and a purple or turquoise sweater. I love the color, the heel, and the clasp buckles on this boot...and that they're not the Uggs worn by practically everyone in Boston.
#168 Felecia on 2010-11-19 19:03 (Reply)
i love the chatsworth! with dark skinnies and a chunky fair isle sweater, it would be so perfect for the holidays!
#169 Linda on 2010-11-19 20:03 (Reply)
I would definitely pick the ladyfish boot! Too cute.
#170 Kris on 2010-11-19 20:16 (Reply)
I would choose the Sperry Top-Sider Boots! You can make a dress less dress and an feminine outfit more edgy! LOVE!
#171 Hang (Homepage) on 2010-11-19 21:47 (Reply)
I would love love love the dark brown ladyfish boots and I would wear them with dark skinny jeans and a chunky sweater.
#172 michelle on 2010-11-19 22:02 (Reply)
I would wear the Ladyfish Boot with thick tights and a sweatshirt b/c the boots look so comfortable.
#173 Phoebe on 2010-11-19 22:06 (Reply)
The Chatsworth Boot would be my choice I would wear them with my skinny jeans and a sweater.

#174 Sharon Rooney on 2010-11-19 22:08 (Reply)
I would choose the Chatsworth boot! I have been considering getting light (cream/white) boots for this season and these would be ADORABLE. I would appreciate the warmth and the fact that they are waterproof as I live in Wisconsin and it gets COLD here. I have to wear a skirt to work every day because of my school's dress code and these would be amazing to pair with many of my skirts and drapey cardigans.

#175 Nicole on 2010-11-19 22:42 (Reply)
I would totally chose the Chatsworth boot. They look so warm and are so beautiful! I'd probably wear it jeans and a long white sweater.
#176 chithra on 2010-11-19 23:44 (Reply)
I would definitely choose the Ladyfish Boot in Barley, I am swooning over it. I would pair it with light wash skinny jeans, a white tee and a big warm sweater. Maybe even get crazy and add a comfy scarf.
#177 Marta on 2010-11-20 00:06 (Reply)
I would pick the Chatsworth boot. I love the wedge, they look so comfy and warm! I would wear them with dark jeans, a cable knit sweater, and a scarf. So cute and practical, I can think of hundreds of ways to wear them.
#178 Nikki (Homepage) on 2010-11-20 02:15 (Reply)
What a great giveaway!! I would love the Bayshore Tall Boot! I would wear it with a pair of skinny jeans or dress, tights and of course, lots of layers!
#179 AB (Homepage) on 2010-11-20 02:38 (Reply)
I would pick the Northstar Boots for sure! Is it wrong to wear leggings everyday in the winter with these boots? Hope not!
#180 Gunita on 2010-11-20 02:56 (Reply)
I would pick the Bayshore Tall Boot in Tan. I would pair them with skinnies, a casual top and a chunky sweater for the perfect low-key weekend look!
#181 Whitney on 2010-11-20 10:10 (Reply)
I would love to get the Bayshore Tall boots, styled with skinny jeans and comfy plaid top!
#182 Meghan O on 2010-11-20 10:41 (Reply)
Bayshore boots are so cute! :-)
#183 Liz on 2010-11-20 11:22 (Reply)
The Ladyfish boot! I'd pair it with jeggings and a chunky sweater.
#184 Karen on 2010-11-20 11:25 (Reply)
I would pick the Chatsworth boots, and I would rock them with leggings and a sweater dress.
#185 Mrs. Kinne (Homepage) on 2010-11-20 11:26 (Reply)
I would choose the Ladyfish boots! i've always loved the dark color of these and that there is a bit of versatility to them. whether with a dress, leggings, jeans, etc - fabulous!!!
#186 DeAnna (Homepage) on 2010-11-20 11:54 (Reply)
I'd get the Ladyfish boots. I can picture them with my dark wash peg leg jeans and a checkered button down and a necklace with a leather accent
#187 Jess on 2010-11-20 13:29 (Reply)
Ladyfish! With dark skinny jeans, a wool overcoat; this would be perfect to keep me warm in the dead of winter!
#188 charlotte on 2010-11-20 13:36 (Reply)
I've loved the Chatsworth boots ever since you styled them! I'd wear them with dark skinny jeans, a chunky grey sweater, and turquoise accessories.
#189 Jenna on 2010-11-20 14:20 (Reply)
I would pick the Chatsworth Boots. There's so much you could wear them with - I would probably rock leggings with an oversized off the shoulder sweater or skinny jeans with a creamy fitted sweater.
#190 Iris on 2010-11-20 15:12 (Reply)
The Chatsworth Boot
I'd wear it with tights and a sweater dress.
#191 Rebecca on 2010-11-20 15:25 (Reply)
I'd go with the Chatsworth boot! They'd look perfect with black leggings, a white tunic tank top and a thick fair isle cardigan. Great boots for the winter, cute and warm!
#192 Angela (Homepage) on 2010-11-20 15:55 (Reply)
I am from Minnesota so I would have to pick the Northstar black boot because we are bound to get above knee length amount of snow at some point! I love the combat look of the boot and that they are tall and would keep me warm. I would pair it with a pair of skinny jeans, darker jean denim or black denim, and a longer off the shoulder shirt and maybe tuck it in or half tuck it in. I also would pair it with a long necklace. I would wear a nice cropped blazer over it, and of course a huge puffy jacket with mittens a hat and a scarf if i go outside into the blizzard!
#193 Molly S. on 2010-11-20 16:44 (Reply)
I really like the Women's Chatsworth Boot. I would wear it with jeans and a cozy sweater, though it's a pretty enough boot for me to consider buying leggings to wear with it.
#194 Jen on 2010-11-20 20:08 (Reply)
I would pick the Chatsworth; they are gorgeous and look super warm as well!
#195 AliciaS on 2010-11-20 20:43 (Reply)
I love the Ladyfish boot! I'd probably put it with some dark wash skinny jeans, and a flowy girly top.
#196 Stephanie Burkholder on 2010-11-20 20:43 (Reply)
I'd want the Bayshore and I'd style them with skinny jeans and an oversized cable tunic length sweater. Throw on some chunky jewelry and it's good to go!
#197 Cupboard Love (Homepage) on 2010-11-20 22:37 (Reply)
I'd love the chatsworth. They look very luxe, yet comfortable and warm.
#198 Joanna on 2010-11-20 22:57 (Reply)
I'd pick the Bayshore Boot... I'd wear it with medium wash skinny jeans, a red plaid button-up shirt, and a large chunky gray sweater to complete the comfy, yet stylish look!
#199 Lillian Cheng on 2010-11-20 23:25 (Reply)
I would go with the Bayshore boot in tan, and wear it with dark denim skinny jeans, my camel v-neck sweater and possibly a leopard scarf!
#200 Andrea on 2010-11-20 23:30 (Reply)
I would love to win the Women's Ladyfish Boots! I grew up in New England and fell in love with winter shoes and boots with thick dark leathers and durable,comfy, stylish interiors to keep my tootsies warm. It was pretty hard to do when there was four girls and my parents were trying to make ends meet- but we did well enough finding discounts and sales. These remind me of warm feet, which was a real treat in those fierce winters. I can still be stylish and put together a rocking outfit to go with these even at my age of 54 yrs old and not 14! I love fashion and as an artist, I do not run with the pack so to speak. Hope I win!
#200.1 Yvonne Rahmes on 2010-11-21 03:43 (Reply)
I would love a pair of the Chatsworth boots. I'd wear them with dark wash jeggings and my favorite grey turtleneck tunic sweater. Perfect for a cold, windy day!
#201 Sarah on 2010-11-20 23:58 (Reply)
I'd love the northstar boot... paired with dark grey leggings, a slouchy white t, military shirt, high ponytail. And with dangly earrings, patterned scarf, a large cuff or gold watch. Too many options!
#202 Jennifer on 2010-11-21 01:55 (Reply)
Oh man, hard to choose between the last two choices - I love them both soooooo much.

I'd wear either of them with my shorter skirts, my jeans, my khakis... uhhh... EVERYTHING ALL THE TIME!!!
#203 Sandra on 2010-11-21 06:25 (Reply)
I love both the Ladyfish and the Bayshore Tall boots- I can imagine fulfilling my New England fantasies here in Southern California by pairing them with leggings/jeggings (can't believe that word is now part of my personal lexicon...) and and my new super-cozy Fair Isle Kensie sweater. Thank you!
#204 Yvonne S on 2010-11-21 08:15 (Reply)
I LOVE the Sandfish boots! Living in FLA...the name screams FLA style. I am 47 but love stylish, fun "things" and would wear these with skinny jeans slightly rolled to expose the boot.
#205 Kristie on 2010-11-21 08:44 (Reply)
lady fish! i would wear them with a big chunky scarf!
boon1211 at gmail dot com
#206 becky on 2010-11-21 10:20 (Reply)
Love the Chatsworth style with a corduroy skirt, tights, and a sweet top!
#207 Katie F on 2010-11-21 12:26 (Reply)
I would wear the bayshore tall boot with a bold-printed oversize sweater, with a belt, and a pair of leggings, or legging jeans. The boots are subtle, but still make a statement, so I wouldn't want to overwhelm them on the bottom, but I would try to bring in some bright colors with the jewelry because I like to add a little excitement to my clothes in winter.
#208 Bri on 2010-11-21 12:43 (Reply)
I would wear the Chatsworth boot with a pretty gold pleated skirt and button down shirt.
#209 Jessica Smith on 2010-11-21 13:10 (Reply)
I love the Bayshore Tall!!
#210 Shelby on 2010-11-21 13:28 (Reply)
Hands down I'd pick the chocolate Ladyfish, fully laced, worn with short shorts, tall socks, gold belt, down vest, wool knit sweater, and my LV logo clutch. Perfect.
#211 TheStyleSmith on 2010-11-21 14:52 (Reply)
I'd choose the Ladyfish Boot which would make a great addition to my wardrobe. What a fun twist on this boot and they could be so versatile. It could be worn with of course leggings and a great sweater or add some edge to a skirt. The possibilities are endless with this boot.
#212 Megz on 2010-11-21 16:08 (Reply)
I love the Bayshore Tall Boot. Fur is in this year, and this pair is just lovely. I would pair it with skinny jeans, simple tee, and a coat.
#213 Karen on 2010-11-21 16:23 (Reply)
I love the Bayshore Tall boot! I'd wear it with leggings, a comfy oversized sweater or sweater dress, a knitted beret, and a matching necklace.
#214 Lucia on 2010-11-21 19:23 (Reply)
I've never had a pair of boots, and I came across this post! I would definitely pick the black bayshore tall boots. They look super comfy, and I'd pair them with leggings and a sweater dress.
#215 Kim on 2010-11-21 19:37 (Reply)
If I won, I would pick the Chatsworth Boot! ;-) I absolutely love the style of this boot with the toggles! It is difficult to find winter boots that are both cozy and stylish, but these boots do the job well! I also think the neutral color is great because it will match well with anything. I would definitely wear these boots over jeans along with my cozy winter sweaters and scarves!
#216 Kelsie Cardio on 2010-11-21 21:51 (Reply)
I'd pick the Bayshore Tall Boot and wear it with a button down red plaid flannel shirt with black leggings!
#217 Tami on 2010-11-22 03:13 (Reply)
I would pick the Northstar boots in brown because for me it lends more versatility. Dress it up or dress it down. I tend to dress more feminine and these boots will keep any outfits grounded.
#218 Ubie on 2010-11-22 04:19 (Reply)
I LOVE the Northstar boots in black. I'd probably wear them with just about anything, but I can see them looking great with skinny jeans, a brightly coloured tunic and a cloche hat. They would also rock paired with a skirt.
#219 Bree on 2010-11-22 05:39 (Reply)
I like the Ladyfish boots, both in dark brown and tan. I would wear them with dark wash skinny jeans, a dark polo, and a bright scarf, perhaps in blue.
#220 May Chow on 2010-11-22 11:37 (Reply)
Oooh....hard to decide between the Sandfish and the Northstar--both would look great with a slouchy cardigan or sweaterdress with leggings. They'd also look great with jeans.
#221 Shannon (Homepage) on 2010-11-22 11:52 (Reply)
I'd definitely rock the bayshore tall boot with skinny jeans
#222 Sarah K on 2010-11-22 12:01 (Reply)
I would wear the Sandfish boot with leggings or dark wash skinny jeans!
#223 Anne Knab on 2010-11-22 12:14 (Reply)
It's a toss up between the Ladyfish boot and the Snug Harbor.
#224 Kim on 2010-11-22 13:06 (Reply)
It's a tough choice, but I think I'd go with the Bayshore. I'd wear it with some skinny jeans or leggings, a long, loose top and a comfy sweater. i'd probably want to sprinkle a long necklace and cute ring on top. :-)
#225 Amy on 2010-11-22 14:35 (Reply)
I would definitely pick the Chatsworth Boot! It would be perfect for the winter season in New York paired with denim shorts, black leggings and a heavy coat on top.
#226 Tiffany on 2010-11-22 14:51 (Reply)
Defintely the Bayshore in Black! I'd pair it with leggings or Skinny jeans...or even bootcut jeans...a cozy sweater or just my fave "Carmel" sweatshirt and some skinny JCrew sweatpants for lazy weekends! They are such cool boots!
#227 Kristine on 2010-11-22 15:09 (Reply)
I would pick the Ladyfish. I would pair it with skinny jeans, a cardigan, cute tank and a scarf!
#228 Jenny on 2010-11-22 15:51 (Reply)
I'd love either the Northstar Boot in black, or Chatsworth Boot. They're both fantastic, and I could seriously use me some winter boots! I'd wear them with everything, jeans or tights and a skirt, or even dress pants!
#229 BrieCS (Homepage) on 2010-11-22 16:12 (Reply)
I love the Northstar boot in brown, but it is also amazing in black. I'd pair it with leggings, and underneath the boots I would wear knee-high socks in a thick, wooly material to compliment the rugged feel of the boots. The socks would peek out from the top of the boots just a bit. On top, I'd wear a flowy white top, of which I have an abundance in my closet because they go with everything! I'd top the shirt with a mismatch of bold necklaces, and then top that off with either a structured velvet blazer (I'm looking for the perfect one) or a shaggy fur vest. This look would be perfect for the cold weather I'm expecting when I travel to Germany in a few months :-)
#230 Tina on 2010-11-22 16:58 (Reply)
I would pick the Sandfish boots because of how versatile the color is. I can just imagine myself clad in a pair of dark wash skinny jeans, a plaid button-up, and a warm light-weight, knit gray sweater on top. Very cute for fall!
#231 Simona on 2010-11-22 17:43 (Reply)
Made a mistake with the name of the boot I would pick -- I meant to write Ladyfish.

#231.1 Simona on 2010-11-22 17:48 (Reply)
I would wear the dark brown ladyfish boots, with indigo skinnies, and a chiffon blouse tucked in with a menswear gold watch
#232 Shenique on 2010-11-22 20:29 (Reply)
bayshore tall boot!!!!
#233 julie on 2010-11-22 23:12 (Reply)
I go crazy for boots, nice coats, and scarves--that's why I love winter :-). All of the Sperry top-sider boots are great, but I especially love the Chatsworth boot! I feel like it's a classic staple that won't go out of style any time soon--it's not necessarily couture but it is cute and wearable! There's something very light, feminine, and rich about it.
I feel like the other boots are a bit riskier and although they would definitely compliment the right outfit, I don't know if I could pull them off next fall.

When I shop for boots, I look for something classic that can adapt to any style. For this winter, I would pair it with dark skinny jeans and a grey over-the-shoulder/boat neck sweater. As for accessories, I would probably just wear a chunky white beanie/beret and a small understated necklace. If the weather was particularly unfriendly, I would wear a quilted coat. Overall, very comfy and wearable--which is exactly what this boot seems to be.

Although this look is common and perhaps overdone, the beauty of this boot is that it can adapt to so many styles--I know I would definitely be able to wear it a different way next year! Thanks :-)
#234 Ann on 2010-11-23 02:22 (Reply)
chatsworth! i would wear them with skinny jeans, a great cardigan and a scarf! perfect for winter months!
#235 Christine on 2010-11-23 09:00 (Reply)
Those Ladyfish boots give me funny feelings in my tummy, the kind only cute boys or seeing a perfect cheesecake tends to give me.
I have an artist friend who has a vaguely similar pair of boots, and my style would definitely be inspired by her. The boots would go great with black leggings under a colorful basic top, a cropped leather jacket thrown on and a patterned scarf wrapped loosely around the neck would finish the look.
#236 Mia on 2010-11-23 10:40 (Reply)
What a tough decision! Since I have to pick one,I would choose the Bayshore Tall boot. I would pair it with a pair of skinny jeans, a chunky sweater/cardigan with a paterned scarf (my standard go to now a days).
#237 Erika on 2010-11-23 11:41 (Reply)
top sider boat shoes have been staple of my clothing for years. Super comfortable shoes that last and stand up well to the elements. I like the Abacos Sahara Corduroy shearling boots. They are precious and look like a boot sneaker cross. I would wear them with a chunky cable knit sweater and some skinny jeans tucked right in them.
#238 Kim on 2010-11-23 11:50 (Reply)
Since the choices are on the other selected boots I would chose the Ladyfish boots in Barley/Suede/Shearling. Those boots just look like Thanksgiving. All the warm fall colors of the season. I saw a perfect dolamn embelshished top at H&M that would look great with them along with the chunky oversized cableknit and jeans.
#238.1 Kim on 2010-11-23 12:03 (Reply)
I like the Ladyfish boot to pair with some jeans and a chunky sweater.
#239 Ellen on 2010-11-23 14:09 (Reply)
Love the Ladyfish boots!
#240 Kay (Homepage) on 2010-11-23 20:59 (Reply)
I'd chose the Bayshore Tall boot! I'd style with dark jeggings and a comfy cowl neck sweater :-)
#241 styleezta (Homepage) on 2010-11-23 21:54 (Reply)
I would choose the Ladyfish Boot in dark brown shearling 2! I love that cute design! I would style them with dark skinny jeans and a long sleeve tee with a fun scarf! Hope I get that chance!
#242 Shelley on 2010-11-23 22:53 (Reply)
I would definitely pick the Bayshore Tall Boot in black because they would be perfect for transitioning from Fall into Winter! I would pair them with my black acid wash skinny jeans, a loose, off-the-shoulder, light gray sweater, a chunky dark gray cable-knit scarf, my favorite dark green leather hobo bag, and of course, some cute black bracelets and bangles :-)
#243 Brooke on 2010-11-24 00:59 (Reply)
The Bayshore Tall Boots are super cute!
#244 Diana on 2010-11-24 01:20 (Reply)
I would choose the Bayshore Tall Boot. I would wear them with some skinny jeans and an oversized sweater.
#245 Ysenia Ramirez on 2010-11-24 03:49 (Reply)
I would wear the Ladyfish Boot in the Brown Deerskin color with olive green skinny cargos and a flowy white v-neck shirt with a long gold necklace and small gold stud earrings. I would top it off with my camel colored trenchcoat (similar to the color of the foldover part at the top of the boot) to class the look up as I imagine I would wear these to a wine tasting close to my home in cold, wet Erie, PA. :-) Maybe a small braid to hold back my side bangs as well! LOVE these adorable boots!
#246 Taylor Larouche on 2010-11-24 08:41 (Reply)
Chatsworth because I love the wedge heel and color.
#247 LuAnn Bowers on 2010-11-24 09:42 (Reply)
i love the northstar boot..i would most likely wear it with black skinny jeans, a t shirt and oversized cardigan. these boots are amazing so i hope to win them
#248 Alesha Dorsey on 2010-11-24 11:06 (Reply)
I have passion for anything nautical so these boots are just my style. I love the Ladyfish Boot in dark brown! :-)
#249 Maggie Hall on 2010-11-24 11:20 (Reply)
I like the Sandfish boot. Looks stylish!
#250 Jellybean on 2010-11-24 11:21 (Reply)
I would wear the Ladyfish boot with a pair of black leggings and an oversized comfy sweater!
#251 Holly on 2010-11-24 12:08 (Reply)
The Chatsworth Boot would be perfect for apres ski or just trekking around my favorite ski village. The wave siping would help prevent slips and falls on the icy walks. I would pair the boot with a pair of trim fitting chocolate pants and a pumpkin colored sweater. I would top it off with a wool camel-colored coat with winter white fleece scarf, hat, and gloves.
#252 Christi on 2010-11-24 13:20 (Reply)
I love, love, love the Chatsworth boot! Sooo adorable! I live in Denver so they would be perfect for the winter weather. I would wear them with skinny jeans, a blazer, and a scarf.
#253 Hannah on 2010-11-24 16:07 (Reply)
I would pick the northstar boot and style it with leggings and a warm sweater dress.
#254 Denisha on 2010-11-24 20:11 (Reply)
I would wear the olive Ladyfish Boot with a shirt dress and knee socks. I would also throw on a few gold necklaces and a distressed leather jacket to complete the look!
#255 Anne Michelle on 2010-11-24 21:57 (Reply)
I would wear the Bayshore Boot with skinny jeans and a t-shirt and a wool coat.
#256 Allison on 2010-11-24 23:25 (Reply)
I want the Chatsworth Boot. I would love to wear them with some jeggings and a comfy sweater. Makes me want to go skiing.
#257 Tatiana on 2010-11-24 23:54 (Reply)
I would pick the Black Northstar boot and style it with black jeans, and a white crop top paired over a black lace body suit. I'd top it all off with some earrings and other accessories.
#258 Alyssa Vu on 2010-11-25 01:21 (Reply)
I'd choose the Northstar boot in black and wear them with black thigh-high socks, high-waisted black shorts, a simple long sleeve, and a coat. Perfect for a winter-y afternoon.
#259 Alicia on 2010-11-25 01:23 (Reply)
The black Northstars would look awesome with tights and a flowy dress! Edgy but chic.
#260 Uyen on 2010-11-25 01:25 (Reply)
These are all awesome but i'd pick the black northstar boot just because black would go easily with my other clothes. I'd wear these with dark wash jeans and a big grey coat and a scarf for day-adventures in the cold.
#261 Phuong on 2010-11-25 01:30 (Reply)
I would pick the Chatsworth boots. They are "to die for" and looked so Awesome in the magazine. They would rock with tights, skinny jeans, a skirt...just about anything!
#262 Hong (Homepage) on 2010-11-25 10:43 (Reply)
I would pick the Chatsworth. I think they'd be adorable with gray tights and a cream or camel sweater dress. Or a little more apres ski with skinny tan corduroys and a slouchy fair isle cardigan. They look so comfy even with the heel.
#263 Victoria on 2010-11-25 22:25 (Reply)
Chatsworth Boot for sure is my favorite!! Very sexy. I would rock it with a Black Tunic dress and black leggins! It would make the boots pop!! :-)))

#264 Lillian Miranda on 2010-11-26 23:44 (Reply)
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