The Budget Babe | Affordable Fashion & Style Blog

Ask BB: Chic Cold Weather Style

Dear BB,
I'm moving to Chicago in less than two weeks and I've completely forgotten how to dress for cold weather! ... Could you possibly do a quick post on what a (few) typical outfit(s) looks like? (If it helps, I'm a woman in her late 20s and need to dress somewhere between professionally and casual, i.e. jeans are fine on most days.) —Fashionably Challenged

Dear Fashionably Challenged,
You're one brave soul to move to the Windy City (my hometown) in the middle of winter, but congrats as you embark on this new adventure!

Here are some tips for dressing for the cold:
Invest in a heavy wool trench-style coat that hits A) mid-thigh or B) falls at or below the knee so you can wear it with dresses/skirts. This will keep you warm and stylish for a good 6 to 9 months out of the year.

Next, invest in at least one thick, warm cashmere scarf, a cashmere/wool hat that covers the ears, and densely knit gloves or leather gloves lined in cashmere. Chicago winters are bitterly cold and you just can't fool around with cheap polyester, it will do nothing against the cold wind.

Also, you'll need tall leather boots with a low heel for walking, if you can afford La Canadienne or Aquatalia, great. Either way, invest in a couple pairs of warm wool socks (I like cashmere or SmartWool, not so itchy) and possibly even silk longjohns from (thanks to Sal over at Already Pretty for the tip on those).

Depending on how warm your office is, you can probably get away with long sleeve layering tees and cardigans, wool blazers, or pretty blouses topped with warm shawl collar cardigans. I mostly wear jeans all year round, just stick to dark washes for work. Black pants work well too.

On "warm" days (over 40 degrees) you can have fun with colored or textured tights and dresses or skirts, so long as you have that warm trench to shield you.

Hopefully this should be enough to get you started, then once you're in the elements you'll have a better sense of what you need. I always loved people watching while riding the El downtown or the bus (especially north-south routes near the lake). Admittedly, I always choose warmth and practicality over style (I know, blasphemy right) but that's what growing up in the Midwest can do to a girl. Good luck!

[Photo credit: Chic winter looks courtesy, including my high school pal Rosie (far left). Love her style!]
I lived in Chicago many moons ago. With global warming maybe it is not as bad as it was some 20+ years ago, but I still say layer yourself well. Hat, scarf and gloves are mandatory. Chicago winds can be brutal!
#1 budget chic on 2009-01-08 08:54 (Reply)
i heart winter clothing.. the scarves & hats.. the boots & skinny jeans... sweater dresses & leggings... love love
#2 Crista (Homepage) on 2009-01-08 10:14 (Reply)
Thanks for the shout-out, lady! And these are some fantastic tips. Gotta put in a plug for mittens, too, though. Unfashionable they may be, but if you get frosty fingertips like me, they're a MUST. Gloves just don't cut it sometimes.

Oooh! And a tip I picked up via Solo Lisa y Nada Mas: Tights beneath leggings. Double-layer happiness without the bulk!
#3 Sal (Homepage) on 2009-01-08 10:52 (Reply)
great tips from one mid-westerner to another, BB!You are right on!
#4 Real Style Real people (Homepage) on 2009-01-08 11:21 (Reply)
I love the outfit in the 4th pic! So cute!
#5 Mishka (Homepage) on 2009-01-08 18:08 (Reply)
Great tips.
What I really enjoyed this winter thus far is my floor length puffy coat. No it's not glamorous or stylish, but it's warm. And when you're in a skirt/dress for formal events, it's NICE to be able to feel warm.

Cashmere is expensive but oh so worth it.
I found that by layering tights then two layers of leggings keeps me warmer than jeans with a pair of leggings. After all, jeans are more porous.
#6 Christina on 2009-01-08 22:04 (Reply)
Love the tips! Being in the mid-west, I can totally feel the winter coldness. Thinsulate coats are a great option too. There are really cute ones that look just like a regular coat on the outside but they're lined with a layer of Thinsulate on the inside. Warmth without puffiness!
#7 Pretty Lil' Things (Homepage) on 2009-01-09 01:56 (Reply)
I think everything pictured here are warm enough for the chilly wintry weather in cold places like Chicago and our place here in CT, except for the 3rd pic from left. I feel like my legs would be trembling with that sheer tights that look like black pantyhose. But maybe that would be good for , as you've said for over 45 degrees.
#8 bingkee (Homepage) on 2009-01-09 16:26 (Reply)
Get a pair or two of water-resistant boots. Wellies are popular here. While Uggs will keep your feet warm, they WILL get dirty from all the dirty slush!
#9 Jade on 2009-01-09 22:12 (Reply)
I, like the other reader, love the 4th outfit. The caramel boots are a nice break from black or dark brown.
#10 Down Comforter (Homepage) on 2009-01-10 16:53 (Reply)
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