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

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 the thigh-high boot. Admittedly it’s a bit trickier silhouette to pull off than say a riding boot or a knee-high style, but don’t stress—we’re 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 it easier to adapt into your everyday wardrobe, think of it as a way to extend the life of your shorter-length seasonal pieces. Thigh-high boots styled with shorts, a mini skirt, or a flowing midi dress are among the infallible styling combos editors always keep on hand. For more ideas on what to do with our favorite piece of footwear this season, keep reading. Let thigh-high boot season officially commence!

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

The best outfits are the ones you can pull off in ten minutes flat, and this one requires little more than a big cozy sweater dress 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. 

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

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

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

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