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!
A great to winterize a summery dress? Style it with thigh-highs and a coat for a more seasonally appropriate feel.
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.
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.
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.
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.
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.
The addition of a furry coat and suede thigh-highs instantly elevates a basic sweater and skinny jeans ensemble.
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.
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.
Alexandre Birman Suede Over The Knee Boots ($995) in Antracite
DV by Dolce Vita Keva Over-The-Knee-Boot ($200) in Black
Nicholas Kirkwood Suede Block Heel Over-The-Knee Boots ($1150)
Sergio Rossi Stretch-Suede Over-The-Knee Boots ($1460)