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Taylor Swift’s Thigh-High Boots Are Trending—Here Are 11 Chic Ways to Pull Off the Look for Fall

Starting at just $50

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thigh-high boots: Collage of Taylor Swift and thigh-high boots
TS: Getty Images; Dana Dickey; Reformation, Amazon, Hordstrom

Real talk: the actual start to fall this year wasn’t when the Kansas City Chiefs faced whomever in their season opener, it was that same night when Taylor Swift dominated the fashion field as a spectator, wearing thigh-high burgundy boots and denim hot pants. Simple, sexy and somehow still sophisticated, her thigh-high boots were the equivalent of fashion shots fired. The singer has gone on to wear the style again: She appeared at the MTV Video Music Awards in another pair of thigh-high boots paired with shorts and a billowy plaid train that parted to show off miles of leg covered in sleek black leather.

This fall boot trend isn’t out of nowhere: Versace, Gucci, Stella McCartney and more showed over-the-knee styles on their fall/winter 2024 runways. I’ve coveted the look since I borrowed a friend’s pair of Prada boots years ago in London, but always thought the look was out of reach of my day-to-day, in both price and wearability. However, now the boots seem to be everywhere, including high street versions being sold at affordable price points (under $200) as well as designer versions demanding indulgent splurge sums. As for wearability, I’m seeing many flat and stacked-heel versions of thigh-high boots that are actually practical—as well as still being sexy. Here are 11 pairs to channel your inner Tay Tay this autumn. 

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How to Wear Thigh-High Boots

If you’re the world’s biggest pop star showing up at your Superbowl champ boyfriend’s football game, you want to go super-short with your look, like Taylor did when she wore denim-on-denim (hot pants and a bustier) on one occasion, and an oversized football jersey-as-minidress on another. For me, I’m wearing the style with a mini-dress or, when the weather gets cooler and I can don tights, shorts. (When I paraded in shorts and thigh-high boots sans tights nonchalantly through my living room, my partner burst out laughing, then later asked for “more slutty outfits”…not the soignée look I was going for.) I like a stacked-heel version for walkability during the day, or even a flat version for maximum comfort. For evening, I’ll take a page from Taylor’s book and jump into a high-heeled boot. As for what to pair 'em with, it’s important to keep accessories and tones quiet if you’re wearing a statement item like a thigh-high boot, for maximum impact and to up the taste level of what, after all, is a fashion item that can easily read more Pretty Woman than polished fashionista. Here are 11 pairs of thigh-high boots to check out, starting at $50.

thigh high boots doen cambria boot duo
Dana Dickey
  • Size Range: 35 to 41
  • Heel: 1 inch
  • Material: all-leather suede upper, leather sole

I love these Doen boots, which sum up the easy California cool that I associate with this woman-run Cali brand. These are especially great since the slouchy leg can be crunched up or down depending on how short your dress or shorts are, and the shaft of the boot is roomy enough to accommodate a skinny denim pant legs tucked into them (the inner zipper on the boot makes folding the denim leg inside easy). And the pointed toe and low heel together create a silhouette that’s more Parisienne cool than rugged cowboy, which is what I’m looking for in a versatile boot. I wore these boots with a short body con dress, a silk shirtdress and over jeans, and have never felt so cool (or long-legged) in my life. Sure, they’re not cheap, but they are less than half the full retail price of Taylor Swift’s boots, and I bet I get more wear out of these than she does.

  • Size Range: 6 to 11, standard and wide
  • Heel: 3.25 inches
  • Material: suede leg, recycled rubber sole

Available in burgundy suede (the color of the thigh-high boots TS debuted), this stacked-heel boot is a lot of style for the money and comes in seven shades. It's one of the most comfortable boots I tried on, and it comes in regular and wide-leg sizes. It’s basically a way to never have chilly legs in your fall skirts again.

  • Size Range: 5 to 11,
  • Heel: 4 inches
  • Material: synthetic upper and sole

Tall and lean, these boots have a back slit at the back of the knee so that there’s enough give to actually bend your legs. (Handy.) The pleather is a good dupe of genuine cowhide, and the covered heel elevates the whole look. It’s also available in black and creamy white.

  • Size Range: 6 to 11
  • Heel: 1 inch
  • Material:  all leather

The cutest innovation in the latest cowboycore aesthetic, these stretched-out cowboy boots are all-leather. They are a classic pull-on design with an inner leg zipper for fit and touches of stylish distressing and Western stitching. One of the season's best cowboy boots for women, costing less than $300? Giddy up!

  • Size Range: 5 to 11
  • Heel: 3 inches
  • Material: calf leather suede

This shape—a skinny high heel, almond toe and wide leg—is the buzziest look in boots this season, and it’s a boon for those of us with muscular calves that don’t prefer to have stretchy material tight to our leg all day, the way some stretch leather boots can fit. This boot’s whiskey-like shade is called bog, and I love it for being a more contemporary version of khaki that will go with everything you’d wear black or brown with. The flare at the top of the boot might overwhelm wearers with super-petite frames or short legs, however the futuristic look of these boots means that if you’ve got the swagger to wear these, you’ll get lots of compliments.

  • Size Range: 6 to 10
  • Heel: 2 inches
  • Material: stretch faux suede upper, rubber sole

These thigh-high boots get raves for their stretch shaft as well as the boot’s thigh opening, which has a taller front layer so that you can get the look of a taller over-the-knee boot without having to encase your thigh all the way around. Available in 13 colors including a gorgeous pink suede, I’m partial to the red sueded fabric for a statement holiday party look that can read as sexy cocktail dressing with a black dress or as festive and casual caroling outfit when paired with jeans. Santa hat accessorizing at your discretion.

  • Size Range: 5 to 11
  • Heel: 2.5 inches
  • Material: faux suede upper, rubber soles

This affordable faux suede pair is great for the way the back of the boot has a short set of laces to tighten around your leg to keep them in place. The soft, thin material of the boot leg is ideal for transitional seasons and mild winters, so you’ll be able to pair these with a flowy dress and show off your outfit without hiding it under layers of sweaters and coats.

  • Size Range: 5 to 11
  • Heel: 3 inches
  • Material: leather upper and sole

If the Venn diagram of thigh-high boots involves materials, price and longevity—in other words, a real investment purchase—then this boot gets a bullseye. Crafted of all-leather in Spain, these boots are made with a three-inch heel that’s high, but still walkable since it is stacked and engineered at an angle that gives your heel maximum leverage. Additionally, the 22.5-inch shaft is going to hide your thighs but not appear so long as to suggest bass-fishing waders. Finally, there’s a back slit at the top of the boot so that every step you take doesn’t push the boot down. Sharp-looking, and well-priced…to boot.

  • Size Range: 5.5 to 9.5
  • Heel: 3 ¾ inch heel
  • Material: synthetic upper, lining and sole

This well-priced boot's secret is that it's made in a really well-done synthetic material that looks like leather and doesn't scuff easily. The almost-four-inch heel is super sexy, and in the red color, we suggest you wear these to cosplay Wanda the sexy witch long after Halloween is over. Or, just wear them with last year's holiday outfit to all your holiday parties or to a dinner date with an all-black ensemble.

  • Size Range: 3.5 to 12
  • Heel: 4 inches
  • Material: stretch nappa leather

A great option for thin frames, this stretch-leather thigh high boot is all-leather and very sexy. It’s pull-on, so it hugs your calves and thighs to stay in place, accentuating all those leg days you’ve worked so hard on. And the pointy toe has a rubber injection outsole to keep it strong as you’re tottering around on the four-inch stiletto heel. This shoe—especially on sale—is a must-have for any drinks date where you can perch on a barstool with your legs crossed.

  • Size Range: 5 to 11
  • Heel: 1.18-inches
  • Material: water-repellent wool uppers, terry knit lining, anti-slip rubber outsole

No need to forgo up-to-date styling just because you're in for soggy weather—this thigh-high boot keeps legs warm and dry with a woolen leg up top and a rubber sole down below. The flexible wool shaft stays put, even if you have to jump over a puddle, and the grip sole keeps you from slipping. All this, plus a bit of lift thanks to a sturdy, squared off one-inch heel.


dana dickey

Senior Editor

  • Writes about fashion, wellness, relationships and travel
  • Oversees all LA/California content and is the go-to source for where to eat, stay and unwind on the west coast
  • Studied journalism at the University of Florida