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10 Ways to Wear Ankle Boots (and 13 Tips To Wearing Them Well)

Image source: Merrick White
Image source: Merrick White

It took me a while to get on board with the ankle boot (or bootie) trend, mostly because I felt like they made women’s feet look chunky, and cut off their legs right above the ankle, making their ankles look wide. Who knows what happened … maybe I just saw too many bloggers looking fabulous in them that I could no longer resist? I don’t know. But now I own four pairs and practically live in them. Also along the way, I’ve discovered a few ways to wear them so they are flattering and don’t make me look like I have fat ankles (thankyouverymuch).

There are so many fun ones out there: wedge, heel, flat, cut-out, laced, buckled, and the list could go on. And they’re so big for fall — you really should own a pair. Don’t be afraid!

Click through for 10 great ways to wear your booties, and a few tips to keep your legs looking slim and fabulous, even with a shoe that doesn’t inherently flatter.

And remember, you don’t need these exact pairs to create great outfits — use these outfits as inspiration to wear your ankle boots well, no matter what style they are!

1. Tucked

Image source: Merrick White

Tucking your pants into your ankle boots creates a long, lean leg line.Tip#1. Most jeans aren’t quite fitted enough at the ankle to allow for this look to work, so a long pair of leggings are your best bet.

2. Rolled Hem

Image source: Merrick White

Rolled or double cuffed jeans are a cute look with booties and allow for a little bit of your ankle to show through, and highlighting that skinny area down there (and keeping your ankles from looking wide). Tip #2.  This look works best with skinny jeans. Straight-legged or wider-legged jeans shorten your leg line when rolled.

3. Cuffed

Image source: Merrick White

When wearing jeans with booties, an exposed ankle is key to keeping your ankles looking as slim as possible. One of the ways to create this gap between the jeans and boots is a cuffed hem. Tip #3. Try this look with a longer pair of skinny jeans, rather than an ankle length pair. A larger cuff (2-3 inches tall) is more flattering.

4. Half Cuff

Image source: Merrick White

One of my favorite looks when pairing jeans with booties is the half cuff. It’s an effortless look and is fun when paired with an oversized tee and sunglasses for a weekend with friends.Tip #4: To make this look as effortless as possible, don’t make your half cuffs match. Keep them about the same height, but roll/cuff them at slightly different angles and widths to make them look effortless and a little haphazard.

5. Layered Socks and Leggings

Image source: Merrick White

The sock trend was hard for me to get on board with, too, but I’m kind of loving it these days. It’s a tough one to pull off though, since it adds bulk to your ankles (the exact thing we’re trying to avoid). But layered over leggings makes for a cute wintery look. Tip #5. Go for a neutral-colored sock to avoid drawing too much attention down there.

Tip #6. Shorter socks (as opposed to knee-length socks) are easier to pull of as well. There is less to bunch, and therefore less bulk.

Tip #7. Don’t ever layer socks over your jeans when you’re wearing booties. Unless they’re jeggings and are very thin material, it will add even more bulk to your ankles. Just don’t do it.

6. Monochromatic

Image source: Merrick White

A monochromatic look is a great way to wear those taller ankle boots. I have a hard time styling my black pair sometimes because they’re a bit taller and cover up my entire ankle. But a pair of black tights and a black pencil skirt creates a sleek long black line that makes it so the height of the boot is irrelevant. Tip #8. Try a fun patterned top to offset the monochromatic bottom!

Tip #9. Try brown tights with brown boots, gray with gray, or mustard with your light brown boots! Related PostTopshop Unveils “Clear Mom Jeans” and We Wish We Were Kidding

7. Colored Tights

Image source: Merrick White

Although the previous look shows tights, this look shows colorful tights, which are a great way to incorporate some color into your outfit.

8. Socks and Bare Legs

Image source: Merrick White

Like I mentioned before, socks are super trendy this year. And although I tend to have a hard time pulling off the look, I have to admit that they look so cool on other people. Tip #10. Keep your socks neutral so they don’t stand out from your legs too much. If your skin is light and your socks are dark, they will cut off the line of your leg and create weird proportions.

Tip #11. When wearing socks with bare legs, keep your skirt or dress hemline above the knee. Anything longer will also cut off the line of the leg and make your legs look short.

9. With a Dress

Image source: Merrick White

Pairing booties with a dress is a fun and non-obvious choice. I like pairing my military style boots with a dress for an interesting juxtaposition. Tip #12. Again, keep the hem of your dress above your knee to create the longest leg line possible.

10. With a Pencil Skirt

Image source: Merrick White

Although I’ve shown you a pencil skirt with ankle boots look already, this look shows them without tights. Typically, I prefer to wear A-line skirts with ankle boots, since the fullness of the skirt makes my feet and ankles look smaller when wearing boots, but pencil skirts can definitely be worn as well and look great.Tip #13. Wear a neutral pair of ankle boots with a slimmer and more fitted skirt. Darker boots draw the eye down toward your feet and can make the outfit feel bottom heavy. Whereas a lighter, neutral boot elongates the leg and keeps the outfit feeling balanced.