12 Thigh-High Boot Outfits with Endless Fall Fashion Inspiration

The arrival of autumn brings many things: falling leaves, pumpkin spice everything, and boot season. While booties and knee-highs are the most common go-to styles, thigh-high boots are a major fashion trend this fall. Also known as over-the-knee boots, thigh-highs are tall boots that go past your knee, creating a dramatic silhouette. While this makes for a fashion favorite (we often see them on the runway), it can be hard to figure out how to wear them in everyday life. To help, we're breaking down just a few of the many ways you can style this statement footwear to fit any occasion or personal aesthetic. Ahead, see 12 thigh-high boot outfits to try this fall.

Cozy and Classic 

The classic (and easiest) way to wear thigh-high boots is with a sweater dress. Wear a shorter dress to show off the boots, or opt for a longer style with a slit to keep you warm. Throw a leather jacket over it to give your look some extra edge. 

Statement Moment 

Thigh-highs are dramatic shoes, so why not go bold with all parts of your outfit? Opt for a pair in a vivid hue, then style them with a graphic turtleneck top and a sparkling midi skirt to make a statement. 

All Matched Up 

When in doubt, a matching set is always helpful to create a pulled-together thigh-high boot outfit. A matching cropped blazer and mini skirt will give your thigh-highs a preppy look while still keeping a degree of edge. 

Bring the Drama 

While thigh-high boots are already eye-catching on their own, if you want to place the focus on these shoes' dramatic silhouette, pair them with a statement coat to turn heads. This pairing is ideal if you’re still getting comfortable showing off your thigh-highs or want to stand out at a party. Wear the look with a midi slip dress for some balance. 

Power Dressing 

Workwear is coming back in a major way this fall, with one of the major trends being the blazer dress. While thigh-highs probably aren't the first thing you think of when it comes to office attire, they look chic and put-together with a coordinating blazer dress and some sunglasses. The ensemble is perfect for a brunch outfit or a fun event. 

Bold and Bright 

While traditional thigh-highs usually stop at the mid-thigh, one popular trend is the extreme thigh-high, which goes so high that it sort of looks like a legging-shoe hybrid. Get some in a fun color, and pair them with a matching mini dress and some statement earrings to create a dramatic look. 

Leather Weather 

Name a more iconic duo than a leather mini skirt and thigh-high boots—we’ll wait. Mini skirts are short enough to show off your statement boots, plus the leather material brings a bit of edge. To tone down the look for daytime, pair these pieces with a turtleneck top for a fall-ready feel that will simultaneously boost your confidence and keep you warm. 

Having a Romp 

To make a foolproof statement, pair some ultra-dramatic thigh-highs with a black long-sleeve romper that keeps your boots center stage while adding a little structure to the look. Just add a handy belt bag, and you’re more than ready for a night on the town. 

Festive Fall Fit 

While thigh-highs are most often featured in bold looks set for nights out, you can also style them more playfully for a day of fun fall activities. Try pairing some simple thigh-highs with a fun fall sweater and some leather tailored shorts—the look is perfect for going to the cider mill or taking pictures with pumpkins. 

Denim Dreams 

Denim is the it fabric of the season, making for a trend-forward variation on a thigh-high boot outfit. Blend simplicity and drama by pairing your boots with a t-shirt and denim midi skirt for an effortless yet unexpected look. 

Buttoned Up 

Sometimes simple is best, even when it comes to a thigh-high boots look. If you simply can't decide what to wear, try pairing black thigh-highs with a loose button-down shirt dress and a bold belt to add a little structure and drama. This easy outfit will have you out the door in no time, looking effortlessly stylish. 

That’s a Wrap

If you're looking to add a little edge to a simple, structured outfit, thigh-highs are the way to go. Pair some classic black thigh-highs with a cropped button-down shirt and a wrap mini skirt for a statement-making yet classic ensemble.