Thigh-High Boots: A Beginner's Guide

Thigh-high boots can easily veer into Pretty Woman territory if they’re styled the wrong way, but you shouldn’t let that deter you from wearing one of the season’s hottest shoe trends. To help you out, we’ve put together a handy beginner’s guide to wearing thigh-highs in a fashionable way. Scroll through for nine foolproof style tips, and shop our picks at the end!

Adding a coat is always a good idea.

Photo:

Style Du Monde

A great to winterize a summery dress? Style it with thigh-highs and a coat for a more seasonally appropriate feel.

Yes, you can wear over-the-knee boots to work.

Photo:

Timur Emek/Getty Images

Want to get away with wearing them to the office? Just make sure to pair your boots with a skirt that’s long enough to cover any leg (at least to the knee) and add a crisp button-down for extra polish.

Sweater dresses and thigh-highs are a great combo.

Photo:

Style Du Monde

A long-sleeved sweater dress can look a little odd when it’s styled with the wrong shoes; a pair of thigh-high boots offers a stylish, suitable option.

Borrow from the boys.

Photo:

Vanessa Jackman

On the other hand, you can try a more masculine-inspired look with your thigh-highs, as Man Repeller’s Leandra Medine does in an oversized jacket and striped shirt. The borrowed-from-the-boys pieces help balance the va-va-voom vibe of the boots.

Let your boots lighten up your look.

Photo:

Style Du Monde

If you’re wearing a lot of black or dark tones, a lighter-colored boot provides some contrast and helps soften your look, while maintaining its edgy vibe.

It doesn’t have to be all about the boots.

Photo:

Vanessa Jackman

If you’re anxious about wearing thigh-high boots as the central focus of your outfit, distract from the shoes by pairing them with bold mixed prints.

Take a basic denim outfit to the next level.

Photo:

Style Du Monde

The addition of a furry coat and suede thigh-highs instantly elevates a basic sweater and skinny jeans ensemble.

For subtle allure, just reveal an inch or two of leg.

Photo:

The Urban Spotter

Take your cue from Olivia Palermo, and wear your over-the-knee boots with a miniskirt for a date night-worthy ensemble. The combination will reveal just a sliver of skin for a look that’s sultry yet understated.

Don’t be afraid to mix in other accessories.

Photo:

Vanessa Jackman

If you’re wearing a simple outfit, adding other interesting accents, such as an embellished belt and fringe purse, will make your look feel more complete.

Keep scrolling to shop our favorite thigh-high boots.

Zara Long Leather Boot ($269) in Black

Will you be opting for thigh-highs this season? Tell us how you style them in the comments below!