The Budget Babe | Affordable Fashion & Style Blog

Three Ways to Wear Ankle Boots

Not sure how to wear ankle boots? Read these tips for all body types.
I've gotten a couple requests regarding how to wear ankle boots, which are boots that end at or just above the ankle. These boots are especially hot for Fall 2009, but here are some things to consider should you choose to wear them:

  • If you're tall, you're in luck—for the most part: Ankle boots can make even the leggiest lass look stubby, so use a mirror. Dare to wear your ankle boots with bare legs and a mini dress.
  • If you're short: Pair your ankle boots with tights, leggings or pants that are the same color as the boot to create the longest line possible. Ankle boots have a tendency of visually chopping you off at the ankle, so be aware of this. Try topping your look with a fitted, cropped jacket to elongate your torso.
  • If you're plus size: Go for a monochromatic look on the bottom to slim and lengthen your silhouette. Pair with something like an a-line, 3/4-length-sleeve dress in a body skimming (not hugging) fabric that falls at or just above the knee.
  • Everyone: I'm stating the obvious here, but the higher the heel, the more height you'll get, hence the more likely you are to nail this look. But I love ankle boots with a low-heel, too, since they're more comfortable for daily wear. And anything over 4 inches can start to look vampy. Also, below-the-knee and long skirts don't seem to work with ankle boots no matter what your body type. Looks frumpy.

Here are 3 ways to wear ankle boots now (shown above):
  • Left: With dark tights. On top, you could really wear any number of dresses, but I've chosen a very of-the-moment girly floral dress and black leather jacket combo. Difficulty level: Easy as pie.
  • Center: With cropped pants. Notice how that little chunk of white flesh visually breaks up my leg line? Yeah, it's not the most flattering thing in the world but it does have a fashion-y vibe that I like. You could wear dark tights under your pants to streamline the look (or add warmth when its cold). Try this look with harem pants if you're uber brave; cigarette pants if you're like me and slightly less of a risk-taker. Difficulty level: Hard
  • Right: With leggings. This season, there are dozens of prints and fabrics to choose from for your leggings. The simplest solution is to pick black leggings with black ankle boots. Tuck in or scrunch over depending on the circumference of the boot shaft. Difficulty level: Intermediate
  • Not shown: Another option would be to wear your ankle boots with skinny jeans, but I figure you've seen enough of me in those. The look is similar to leggings except, of course, you'd be wearing a more substantial pair of pants.

Will you be wearing ankle boots this season? How do YOU style them?

Where did you purchase your ankle boots?
#1 Phinesia on 2009-09-13 11:07 (Reply)
Oops, forgot to mention this too. Those are my new Kalila ankle boots from Target:

#1.1 The Budget Babe on 2009-09-13 19:34 (Reply)
Have you seen anything lately that closely resembles this pair of shoes? I am in LOVE and would like a pair! Obviously a few years too late :-)
#1.1.1 Mandy (Homepage) on 2015-10-04 08:59 (Reply)
Wow excellent tips. I like what you did with outfit 1 and 3 especially thats how I would wear it. I am so short so you are so right, they do make legs looks short. Your legs do look longer when matched with the same color boots, very true!
#2 Dina's Days (Homepage) on 2009-09-13 11:47 (Reply)
This article was great. I love your long blazer. It looks slightly shiny which is nice. Will you share will you found them?
#3 Jem on 2009-09-13 12:57 (Reply)
Oh yes, I meant to do a separate post on this but haven't had time: The blazer is called the Long Boyfriend Jacket from

I love the length and 3/4 length sleeves (no rolling required). I bought it a couple weeks ago w/a gift card and 20% off coupon that I found at So far, so good!
#3.1 The Budget Babe on 2009-09-13 19:30 (Reply)
thanks so much for this post! i'm a shorty so i knew i would need leggings but i wasn't sure what else to wear with them. and i love the ankle boots you're wearing!
#4 giselle on 2009-09-13 13:59 (Reply)
when i wear my ankle boots with skinny jeans, they always "blouse" over the top of them because my legs are so disgustingly skinny. any tips ladies?
#5 Tanya on 2009-09-13 15:10 (Reply)
Super cute!! I love look #2. But no one..NO ONE should wear harem pants!!

#6 Carrie on 2009-09-13 16:17 (Reply)
Brilliant post, Dianna! You've hit the nail on the head with HOW to wear ankle boots with each of the body types. A raised hemline on the frocks is essential. And you look absolutely gorgeous in every outfit! Very inspiring. Love your cuffs!
#7 angie (Homepage) on 2009-09-13 18:30 (Reply)
I love the dress in number 1!! Where did you get it?? Love the blog!!
#8 jennifer on 2009-09-13 18:43 (Reply)
That dress is from forever21...i know because I bought it there for about 15$ and it's really comfortable!
#8.1 Noh on 2009-09-14 02:32 (Reply)
I have a gorg pair of frye ankle boots and I wore them out with a pair of jeggings (full length) and a long tank and leather jacket, and the outfit was seriously fierce! I love my ankle booties and will be rocking them all season!
#9 Peaches on 2009-09-13 19:25 (Reply)
love this article, great advice! As a shortie I find it very hard to find boots that fit me, but I think I may have a pair that doesn't make me look like a midget!
#10 MizzJ (Homepage) on 2009-09-13 23:16 (Reply)
I love those ankle boots!

Where did you get your cigarette jeans? I have been looking for a pair, cheap of course!
#11 Rachel (Homepage) on 2009-09-14 10:02 (Reply)
u look great!
#12 anh (Homepage) on 2009-09-14 10:30 (Reply)
Not a fan of the cropped pants and ankle boots. Maybe being that I am tall it looks like you couldn't get your pants long enough!
#13 Barbara (Homepage) on 2009-09-14 17:13 (Reply)
i've been dying for a pair of ankle boots i can wear with *everything*. I have so many black shoes I want to look for a brown pair xP However, my legs are really scrawny, and I feel the openings for all the ankle boots are so wide. Any suggestions?
#14 Julia on 2009-09-14 17:51 (Reply)
Thank you posting this how-to! I was shy to break out my ankle boots but not anymore! Can't wait to put these ideas into practice...
#15 Sam on 2009-09-14 21:43 (Reply)
loveee ankle boots, but i have a brown pair and am lost as to what to wear it with aside from skinny jeans.. thoughts :(?
#16 Niala (Homepage) on 2009-09-24 15:29 (Reply)
I'm with you. I just purchased some brown ankle boots- I'm in love!They're brown leather with a folded-down cuff. But I'm stumped as to how I should wear them. Can I mix brown boots with black tights? What about boots with work attire? Any suggestions?
#16.1 martha on 2009-10-20 02:05 (Reply)
I looove outfit number 1. where is your leather jacket from?
#17 Ali on 2009-11-16 22:42 (Reply)
This helps, thank you! I'm plus size and boguht a pair of chunky-heeled ankle boots today on a whim and wasnt sure what ensemble to pair them with!
#18 Sarah on 2012-01-14 01:25 (Reply)
I appreciate the fact that you have tips for plus sizes too. Thanks!
#19 Kaitlin on 2012-09-21 10:39 (Reply)
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