I'm Wearing Thigh-High Boots as Much as Possible This Season—Here's How

·10 min read

Real talk: While thigh-high boots may be a fan-favorite among designers, fashion girls, and women everywhere, they aren't exactly the easiest to wear. Coming up with thigh-high boot outfits can feel as taxing as slipping them off at the end of a long day. And while they may elicit step-on-me feelings, they're not exactly the easiest boots to wear to get your steps in, if you catch my drift. But, as knee-high boots and over-the-knee boots have surged in popularity, it's only a matter of time before thigh-high boots inch up even further.

If you experienced existential dread while reading that last sentence, take a deep breath—I'm about to prove to you that thigh-high boots actually aren't that difficult to style. The best thigh-high boot outfits of the moment are easier to replicate and wear than they were in previous seasons. You'll just have to keep scrolling to see for yourself.

WHO: Noelle Venegas

WHAT: Shoedazzle thigh-high boots

WEAR: Turtleneck sweater dress with a slit and snake-print thigh-high boots.

The best part about wearing thigh-high boots is being able to show them off, so whether you own a pair of snake-print boots or another bold pair, be sure to wear them with a dress with a high-slit to show off your boots in all their glory.

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Steve Madden Vava Blue Snake ($120)

WHO: Madeline Briell

WHAT: Charcoal sweater; Missguided boots.

WEAR: Oversize button-up dress, sweater, and thigh-high boots.

Who said you need to purchase a whole new look to suit your boots? Just pull out your oversize white button-up, layer a sweater over it, and slip into those thigh-high boots. Voila!

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Aldo Dweradia Over-the-Knee Boot ($130)

WHO: Jeniese H

WHAT: Time and Tru Felt Fedora ($11); Terra & Sky V-Neck Sweater Dress; Brinley Co. Over-the-Knee High Heel Faux Suede Wide Calf Boots ($64).

WEAR: Thigh-high boots, a mini sweater dress, and a hat.

If you’re seeking a thigh-high boot outfit you can replicate at home with ease, look no further than this outfit from Jeniese. Pair your boots with a sweater dress, and top it off with your favorite hat for a simple yet chic look.

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ASOS Kendra Stiletto Thigh High Boots ($64)

WHO: Oriane Adjibi

WHAT: Primark sweater; Black Cycling Shorts ($4).

WEAR: Turtleneck, biker shorts, and thigh-high boots.

PSA: You don't have to dress up in a full head-to-toe 'fit to make use of your thigh-high boots this season. Just take a cue from Oriane Adjibi, and pair your shoes with biker shorts and an oversize turtleneck for a casual yet fresh take on styling your boots.

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Vince Camuto Demerri Boots ($223)

WHO: Archie

WHAT: Luxe to Kill Cream Extreme Crop Roll Neck Jumper ($27); Chocolate Brown Knitted Bralet ($20); Brown Oversized Joggers ($24); Truffle Collection shoes.

WEAR: Bolero sweater, knit bralette, sweats, and thigh-high boots.

Want another informal way to style your thigh-high boots? Try pairing them with sweatpants. Yes, you read that right. Throw on a knit bralette with a bolero sweater and tuck your favorite joggers under thigh-high boots for a cozy look. It's a win-win in our book.

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Jeffrey Campbell Parisah Over the Knee Boot ($165)

WHO: Laura Dittrich

WHAT: Celine sunglasses; C/MEO Collective dress; Saint Laurent Faux Patent-Leather Over-the-Knee Boots ($1995).

WEAR: Black dress and thigh-high boots.

The simplest way to style your thigh-high boots is by pairing them with your favorite LBD. It's a look that works every time.

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Zara Tall Shaft Heeled Boots ($119)

WHO: Yatri Pabari

WHAT: H&M sweater; Arket High-Waist Culottes ($79); Jones Bootmaker Brescia Leather Knee Boots ($219)

WEAR: Turtleneck, sweater vest, Bermuda shorts, and thigh-high boots.

If you can't imagine wearing a dress during the winter but also struggle to wear your thigh-high boots over jeans or pants, then I recommend pairing them with Bermuda shorts. Not only will you get to show off your shoes, but your legs will stay warm in the process.

Franco Sarto Pisa Over the Knee Boot ($169)

WHO: Bianca Valle

WHAT: Gucci sunglasses; Versace earrings; Vintage blazer; Mango Organic Cotton Essential T-Shirt ($10); Jacquemus Le Chiquito Mini Bag ($499).

WEAR: Blazer, T-shirt, shorts, and thigh-high boots.

For the Bermuda-short adverse, you don't have to toss out the thought of pairing your thigh-high boots with shorts. Just swap out the Bermuda cut for your favorite blue-jean shorts, and you've got an equally chic look. Pro tip: The boots are the focus of this look, so don't be afraid to opt for your boldest pair of thigh-high booties.

Cult Gaia Yasmina Suede Over-the-Knee Boots ($798)

WHO: Emmanuelle Koffi

WHAT: MM6 Maison Margiela Logo-Print Headband ($200); IRO Paris coat; Furla boots.

WEAR: Fringe jacket or fleece top, tank top, mini skirt, and thigh-high boots.

You don't have to miss out on thigh-high boot outfits if you live in a warmer climate. In fact, you can get creative with your look by wearing your boots with fewer layers. Pair them with a fringe coat or fleece jacket (depending on the temperature) and a simple tank and mini skirt for a warm-weather look that allows you to wear your boots without overheating.

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Tony Bianco Holli Boot in Black ($280)

WHO: Morgan Fitzpatrick

WHAT: Public Desire Brandy Stone Western Block Heeled Knee High Boots ($75); MTF Label bag.

WEAR: Oversize blazer, thigh-high boots, and micro-handbag.

If you live in a warmer climate, then this thigh-high boot outfit is for you. Wear your favorite oversize blazer as a dress, and slip into your thigh-high boots for a look that rivals your city's heat.

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Cape Robbin Over the Knee Western Cowgirl Boots With Chunky Block Heels ($36)

WHO: Maggie McCormack

WHAT: Sororité vintage blazer; Nasty Gal belt; Simmi shoes.

WEAR: Oversize blazer, sweatshirt, belt, and thigh-high boots.

If the thought of wearing just a blazer made you shiver, don't fret. You can still pull off a similar thigh-high boot look by throwing a sweatshirt or sweater underneath your oversize blazer to add another layer of warmth to your outfit.

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Dundas X Revolve London Boot in Snake ($698)

WHO: Kizhan

WHAT: H&M Rib-Knit Turtleneck Sweater ($15); Zara skirt; Stuart Weitzman Highland Boots ($895).

WEAR: Matching tonal sweater and slip skirt, mismatching thigh-high boots.

When it comes to perfecting a thigh-high boot outfit, it's important to get comfortable playing with various colors, fabrics, and combinations. Try styling your thigh-high boots this season by pairing them with your trusted silk slip skirt and a matching sweater. The mix of fabrics along with your shoes will give off an expensive aura (even if your look didn't break the bank).

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Raye River Boot in Black ($348)

WHO: Yoyo Cao

WHAT: Jimmy Choo Beca Over-the-Knee Boots ($1550); Anne Vest Cloe Coat ($2465).

WEAR: Oversize statement coat and thigh-high boots.

Depending on your height, an over-the-knee boot can become a thigh-high one. But there's no need to fret because you can still make this look work for you no matter what. Just pair your boots with an oversize coat for a look that's precisely on-trend this season.

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Staud Aimee Boot Black Vegan Leather ($495)

WHO: Georgia

WHAT: Lespecs sunglasses; Zara Faux Leather Oversized Blazer ($70).

WEAR: Black mini dress, leather blazer, and thigh-high boots.

The other staple outerwear piece of the season (other than a fun coat) is a leather blazer. And blazers just so happen to be the perfect piece to pair with thigh-high boots. I recommend taking the seasonal staple to the next level by doing a head-to-toe monochrome look (in black or any hue of your choosing).

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Tory Burch Lila Heeled Tall Boot ($578)

WHO: Isabelle Tounsi

WHAT: Men's blazer; H&M Faux Leather Leggings ($25); Don Donna bag; Shein boots.

WEAR: Oversize blazer, leather leggings, thigh-high boots.

Let's be real: Leggings have been the bottoms of choice (if we're wearing pants at all) this year. But if you are feeling compelled to dress up a bit, then you can slip into a pair of leather leggings and your thigh-high boots for an effortless look that appears far more polished than it actually is.

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Shoedazzle Meya Stiletto Boot ($74)

WHO: Julia Comil

WHAT: Long Champ sweater; Barbara Bui skirt; Nicholas Kirkwood Lexi 70mm Snake-Print Leather Boots ($1395); Staud Soft Moon Bag Cream ($395).

WEAR: Holiday sweater, leather skirt, shoulder bag, and thigh-high boots.

As you can tell, leather separates are by far one of the season's biggest trends. But if you're not a fan of leather blazers or pants, opting for a leather skirt to go with your thigh-high boots will work wonders, too.

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Jessica Simpson Ammira Over the Knee Boot ($139)

WHO: Jasmine Fox-Suliaman

WHAT: Missoma Lucy Williams Gold Chunky Waffle Hoop Earrings ($143); Staud dress; Steve Madden thigh-high boots; Vintage clutch.

WEAR: Maxi turtleneck dress, thigh-high boots, and a statement clutch.

Still here, but not convinced of the power of thigh-high boots? I can personally attest that these boots are a staple you can wear season after season. And while thigh-high boot outfits require a bit of creativity, you won't regret wearing them.

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Keeyahri Zerina Pointed Toe Over the Knee Boot ($1199)

These boots would look so good with this Paco Rabanne Jacquard-Knit Turtleneck Maxi Dress ($790).

Shop more thigh-high boots:

Free People Chase Second Skin Over-the-Knee Boots ($248)

The season's trendiest thigh-high boots also happen to be flats, which I'm very much here for.

Steve Madden Vivianne Pink ($250)

Sparkly pink boots? Yes, please.

Nicholas Kirkwood Jazzelle Over the Knee Boots ($678)

No lie, I allocate at least twenty minutes a week to staring at these boots.

Charles & Keith Black Textured Thigh-High Boots ($93)

You can't go wrong with black suede thigh-high boots.

Nicolette Nichelle The Briar Boots Denim ($50)

Leave it to a Black-owned, Texas-based small brand to create the coolest thigh-high boots I've ever seen.

Simon Miller Vegan Tall Scrambler Boot ($530)

Imagine these boots with a pleated skirt and sweater.

Dolce Vita Nicolette Over-the-Knee Lug Boots ($99)

These would go perfectly with your skinny jeans.

French Connection Liv Over-the-Knee High-Heeled Boots ($90)

White boots are never a bad idea.

Brother Vellies Ronstadt Suede Boots ($995)

Hello, suede boots of my dreams.

Michael Kors Ridley Over the Knee Boot ($188)

You can wear these all winter.

Olivia Miller Madison Lug Sole Tall Boot ($110)

Talk about a statement boot.

Pretty Little Thing Black Diamante Slouch Thigh High Boot ($129)

I'm pretty sure Rihanna would wear these.

Calvin Klein Sacha Over the Knee Boot ($179)

These boots are a timeless staple.

Next: Knee-High Boots Are Back for Fall—Here Are the Best Pairs Under $350

This article originally appeared on Who What Wear

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