5 Trendy Outfits to Wear With Thigh-High Boots This Fall


(Image credit: @georgia_3.0)

In the case of thigh-high boots, here's where the legendary "can't wait till it gets colder so I can really start dressing" fashion meme firmly applies. They're one of those items you wait all year to finally drag out from the depths of the closet, and now that the leaves are turning orange, it's officially time for thigh-high boots. Admittedly, it's a silhouette that's trickier to pull off than riding boots or a knee-high style, but don't stress—I'm here to provide all the styling lessons needed.

An essential element of cold-weather dressing, thigh-high boots can be a practical choice if you're the type to forgo heavy-duty stockings. To make them easier to adapt into your everyday wardrobe, think of them as a way to extend the life of your shorter-length seasonal pieces. Thigh-high boots styled with shorts, a miniskirt, or a flowing midi dress are among the infallible styling combos editors always keep on hand. For more ideas on what to do with my favorite piece of footwear this season, keep reading. Let thigh-high-boot season officially commence!

Outfit 1: Shorts Suit

Any polished suit is enough to turn heads, but if you really want all eyes on you, try this combination of a shorts set and combat boots. What sets this look apart is the menswear-inspired tailoring juxtaposed with the rugged thigh-high lugged boots. It's unexpected and downright cool.

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Outfit 2: Cozy Turtleneck Dress

The best outfits are the ones you can put together in 10 minutes flat, and this one requires little more than a big, cozy sweaterdress and your best leather thigh-high boots. If you're feeling extra fancy, these Loewe glasses and Khiry earrings are sure to garner all the compliments. 

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Outfit 3: Cropped Tweed Blazer + Denim Miniskirt

In a wave of nostalgia, denim skirts are slowly emerging as a trend this season. One of the most effortless ways to wear one? Thigh boots, of course, and this Chanel-esque cropped tweed blazer. Opt for boots in a lighter color to emphasize the royal blue in of the blazer.

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Outfit 4: Bohemian Floral Dress + Shearling Coat

One of my personal favorite outfit formulas is a billowy floral dress and tall boots. Amp the look up with a dramatic shearling coat when temperatures start to drop.

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Outfit 5: Trench Coat + Sweater-Vest + Leggings

While it may be impossible to layer a pair of jeans or thicker pants underneath thigh-high boots, leggings are thin enough and equally versatile. Elevate it with a chic trench and an oversize sweater-vest.

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Next up, PSA: These Fall Outfits Will Make You Miss Summer Less

Fashion Market Editor

Indya Brown is a fashion editor, stylist, and writer living in Los Angeles. While going to school at Columbia University in New York City, she got her feet wet in the fashion industry interning at Elle magazine, Harper's Bazaar, and New York magazine's The Cut. After graduating in 2016, she joined The Cut as a fashion assistant, eventually working her way up to fashion editor. There, she worked on a multitude of projects, including styling inbook feature stories for New York magazine's print issue, writing and pitching market stories for The Cut, and serving as fashion lead for The Cut's branded content. While New York has been her home for over 10 years, she moved to Los Angeles in the midst of the pandemic in 2020 for a new chapter. Now she is a fashion market editor for Who What Wear, focusing on emerging designers, rising trends on and off the internet, interior design, and BIPOC creatives and brands. Aside from her duties as a fashion market editor, Brown is also a freelance stylist and writer, working on national print and video commercial campaigns for Sephora, The Independent, and Cadillac. Her bylines also include Harper's Bazaar, Vox, and The New York Times. But once the computer goes down and the emails turn off, she's likely eating her way through Koreatown, hunting down vintage furniture, scoping out new outrageous nail designs to try, or taking a hot cycling class.