Upgrade your winter wardrobe with these fail-safe styling formulas—no hosiery required.
I used to be intimidated by the idea of wearing thigh-high boot outfits. Although the style designed with lengthy legs reigned supreme across several Fall 2024 runways—including the catwalks at Gucci, Chloé, and Fendi—I wasn’t convinced that I, a self-proclaimed minimalist, could pull off this bold boot trend. But I’ve since had a change of heart, thanks to none other than Rihanna.
The snazzy pop star recently proved that styling thigh-high boots doesn’t have to be daunting. For an evening on the town, she slipped into over-the-knee boots alongside a zippered sweater dress and an oversized clutch drenched in wine red. Rihanna kept her accessories to a minimum, choosing to only incorporate wide-framed sunglasses and hints of gold jewelry. By taking a straightforward styling approach, she tackled the thigh trend in a way that felt, well, approachable.
Inspired by RiRi’s going-out look, I filled my winter mood board with thigh-high boot outfits plucked straight from the street style scene. Most looks feature easygoing cold-weather essentials like relaxed sweaters, rugged leather jackets, and sturdy straight-leg jeans. Others embrace more of a statement through fringed jackets and faux fur coats. More than anything, these sleek uniforms boast a sense of practicality—there’s no denying that full-length boots provide extra warmth—no tights required.
Ahead, you’ll discover all the thigh-high boots outfit ideas I plan to take for a spin this season. And given that they are both feasible and functional, I’m sure you’ll want to do the same.
Partially Preppy
According to the fashion set, preppy outfits are all the rage. If you’d like to play into this look in a way that doesn’t scream “school girl,” give your outfit a grown-up edge with sultry thigh-high boots. Top things off with a khaki midi skirt and a crisp button-down shirt layered beneath a sweater.
Corporate-Inspired
Put a professional twist on your thigh-high boot outfit with a tailored blazer that’s sharp around the edges. While this look is a bit too risqué for the office, it will fit right into your evening-friendly wardrobe. Don’t forget to cinch your blazer at the waist with a belt to really tie the look together.
Shed a Layer
For warm winter days that feel more like spring, pair your boots with a cardigan and a mini skirt or shorts that hit at the thigh. Wear a coordinating set to earn extra style points. There’s just something about a matching fit that feels exceptionally polished.
Have Fun With Fringe
Champion the fringe trend with a playful jacket trimmed in decorative strands of fabric. Since this piece makes quite a statement, stick with a neutral color palette to balance things out.
The Furrier, the Better
Shaggy faux fur coats are cold-weather classics, so why not give this eye-catching outerwear style a try? Liven things up with a little black dress and a pair of striking thigh-high boots plastered in a warm hue of burgundy.
Plain and Simple
As someone who lives by the style memo, “less is more,” this look instantly spoke to me. I love how this fashion week showgoer chose an all-black outfit that allowed her thigh-high boots to take center stage. The opulent handbag to match is Chef’s kiss!
The Cherry on Top
Lean into saturated shades with a vibrant accessory—like a cherry red bag that commands attention. For the rest of your look, consider subdued shades like olive green and black thigh-high boots to ground the outfit.
Leather Layers
For a grungy feel, opt for a pair of lug sole thigh-high boots with a combat-inspired silhouette. Complete this biker-chic look with an edgy leather jacket that flaunts a lived-in feel.
Dress Like a Princess
Princess Diana had many styling hacks under her belt, one of which was her go-to “boot tuck.” Follow in the fashion icon’s footsteps by slipping a pair of thigh-high boots over straight-leg jeans. Throw a blazer over your shoulders, and you’ll look like an English country-style poster girl (in the best way possible).
Keep It Neutral
If you don’t want to waste any energy trying to come up with a thigh-high boot outfit, use this look as your source of inspiration. Simple shades like black, cream, and tan give off a streamlined aesthetic.
