How to Wear Ankle Boots

This post has now been updated for 2014! Click here to see it.


It’s time for the long-awaited next installment of “How to Wear”! This time I’m talking ankle boots or booties. They’re so darn adorable, but they can be hard to wear. They cut off your legs at the ankle (as you might have guessed), which can make you look shorter, which in turn can make you look fatter. I don’t mean to speak for all women, but I tend to shoot to look more like Gisele and less like Danny Devito. The key to wearing ankle boots is elongating your legs as much as you can while still showing off the shape of the shoe.

Your ankle boot styling options depend on the kind of heel you’re working with, so I’ve split my examples into 3 categories: wedges, flats, and heels.

Wedge ankle boots


Wedge boots are my favorite so I put them first! You get extra height, which makes them easier to wear, but they’re still comfortable. I wear my wedge ankle boots with cuffed skinny jeans all the time. Skinny jeans make my short legs look as long as they’ll ever look (still not that long). But cuffing them a bit helps show off the shoe. If you have cropped skinny jeans, that would work too.


Wedge ankle boots can work with a skirt or dress too, as long as the hem falls a few inches above the knee. The more leg that’s showing, the longer your legs look. Just keep it decent, OK ladies?

Shop Wedge Ankle Boots: Save // Spend // Splurge

Flat ankle boots


Flat ankle boots are the hardest. They accentuate my lack of height, but I still love them! I wear them with cuffed skinny jeans just like my wedges. You’ll notice in both of the above outfits I tucked in my shirt – if you’re already cutting off the leg line at the bottom, you don’t want to do it at the top too!


Friends don’t let friends wear leggings as pants. Always cover your junk. That said, leggings can be very slimming on your stems, and you can get away with a short tunic. Flat booties with leggings can be a fun alternative to sneakers or flip flops with a super casual outfit.

Shop Flat Ankle Boots: Save // Spend // Splurge

Heeled ankle boots


Heeled ankle boots can be worn almost any way you would wear regular old pumps. They’re a great option for the winter because they’re a little sturdier than pumps and you get more coverage on your chilly feet.

Shop Heeled Ankle Boots: Save // Spend // Splurge

See more How to Wear posts:

Army Jacket     Oxford Shirt     Denim Jacket     Flared Skirt

20 thoughts on “How to Wear Ankle Boots

  1. The more you post about how to dress up flat footwear, the happier I am. I have a back injury and can therefore no longer wear heels at all. I was depressed about this for years and lived in running shoes, but, eventually, I got smart and just started buying nice flat shoes, sandals, and boots. I miss my heels, but at least now I have some variety.

    On another note, I’m short too and have never understood why women mind looking short. I like it. I think it makes me cute and I like that too. I own my stature with pride. My partner loves my shortness and always calls me a “boo, ’cause you’re just little!”

    • I’m a proud shortie too! I think I like flats just as much as heels, just depends on my outfit and mood and what I’m doing. If I’m going to walk very much, I don’t bother with heels because I know I’ll just get grumpy.

  2. Just saw your post and can’t agree enough about the problems with being short (although my mother always said “say petite”)! I have a couple of ankle boots and am always conscious of wearing them and looking shorter (read fatter), but your post now makes me appreciate their versatility. I will try again. Thanks heaps.

  3. Pingback: How to Wear Ankle Boots (Part Deux) | Sarah's Real Life

  4. Pingback: Trend Watch: Two-Tone Boots | Boottique Blog

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s