15 Thigh-High-Boot Outfits We're Re-Creating

last updated 5 September 2024

a thigh-high boots outfit shown on a woman wearing a black leather top with matching leather shorts and black flat tall boots

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 them for yourself.

Oversize Leather Blazer + Sweaterdress + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman standing near the street wearing a black baker boy hat with a black leather jacket, white mini sweater dress, and black thigh-high boots

Who said you must purchase a new look to suit your boots? Just pull out your favorite sweaterdress, layer a leather blazer over it, and slip into those thigh-high boots. Voilà!

ALDO

Astelawan Platform Boot

Oversize T-Shirt + Oversize Sweater-Vest + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman standing against a white wall wearing a black oversize T-shirt under an oversize white sweater-vest dress styled with black slouchy tall boots

If you’re seeking a thigh-high-boot outfit you can replicate at home easily, look no further than this outfit. Pair your boots with an oversize T-shirt and sweater-vest and top it off with your favorite crossbody bag for a simple yet chic look.

Michael Kors

Kelsea Leather Slouchy Boot

Jacket + Tank Top + Miniskirt + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman sitting on stairs outside wearing a fringe plaid jacket over a white T-shirt with a gray miniskirt and black 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 miniskirt for a warm-weather look that allows you to wear your boots without overheating.

Staud

Aimee Boot Black Vegan Leather

Blazer + T-Shirt + Shorts + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman walking across the street wearing a tan blazer over a white T-shirt with denim shorts and orange 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.

Vince Camuto

Sydnie Extra Wide Boot

Button-Down + Wrap Skirt + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman walking down the sidewalk wearing a white button-down shirt with a green cargo skirt and black thigh-high boots

When it comes to perfecting a thigh-high-boot outfit, it's essential to get comfortable playing with color-blocking. Give your thigh-high boots an extra pop by styling them with a colorful skirt and a simple button-down.

Marc Fisher LTD

Genessa 2 Pointed Toe Boot

Oversize Blazer + Sweatshirt + Belt + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman in a park garage wearing a gray blazer over a creme sweater dress styled with snakeskin 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.

Khaite

Snake-Effect Leather Knee-High Boots

Trench Coat + Turtleneck + Midi Skirt + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman standing against a white wall wearing a green trench coat over a turtleneck styled with a gray pleated midi-skirt and red thigh-high boots

Didn't think thigh-high boots could be work-friendly? Think again. Simply style them underneath a midi skirt with a turtleneck and trench coat.

Chloé

85mm Eve Leather Boots

Oversize Statement Coat + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman sitting on a stoop wearing an oversize yellow coat worn as a dress with black 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 an on-trend look this season.

Nomasei

Whisper Over the Knee Boots

Minidress + Leather Blazer + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman sitting down wearing a black minidress with a black leather blazer and black 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).

PARIS TEXAS

Vegas Faux Stretch-Leather Boots

Fair Isle Sweater + Leather Skirt + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman walking down the street wearing a fair isle sweater with a leather skirt and white 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.

STEVE MADDEN

Vava White Boots

Camel Coat + Leggings + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman walking down the street wearing thigh-high brown boots over black leggings with a camel wrap coat with a built-in scarf

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, a camel coat, and your thigh-high boots for an effortless look that appears far more polished than it actually is.

GABRIELA HEARST

Linda Leather Boots

Leather Bomber Jacket + T-Shirt + Miniskirt + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman standing in an art gallery wearing a leather moto jacket over a gray T-shirt with a red pleated miniskirt styled with black thigh-high boots

PSA: You don't have to dress up in a full head-to-toe 'fit to use your thigh-high boots this season. Just take a cue from the look above and pair your shoes with a leather bomber jacket, T-shirt, and miniskirt for a casual yet fresh take on styling your boots.

Schutz

Helena Boots

Leather Button-Down + Matching Shorts + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman walking down the street wearing a black leather top styled with matching shorts and black tall boots

The best part about wearing thigh-high boots is showing them off. Wear them with a leather button-down and matching shorts to show off your boots in all their glory.

Charles & Keith

Davina Buckled Thigh-High Boots

T-Shirt + Denim Skirt + Shoulder Bag + Thigh-High Boots

a photo of a thigh-high boots outfit shown on a woman wearing an ombré T-shirt with a midi denim skirt and black thigh-high boots

Styling denim and boots together may be a tad bit cliché, but it always works. But if you still want to spice up your styling, swap skinny jeans for a denim skirt. Do this, and you'll realize nothing is boring about this combo.

Jeffrey Campbell

Overlook Boot

Maxi Dress + Thigh-High Boots + Statement Clutch

a photo of a thigh-high boots outfit shown on a woman in an art gallery wearing a black turtleneck sweater dress with black thigh-high boots and a clutch bag

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.

Nine West

Sensa Boot

This post was originally published at an earlier date and has since been updated.

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Jasmine Fox-Suliaman is a freelance writer and editor living in New York City. What began as a pastime (blogging on Tumblr) transformed into a lifelong passion for unveiling the connection between fashion and culture on the internet and in real life. Over the last decade, she's melded her extensive edit and social background to various on-staff positions at Who What Wear, MyDomaine, and Byrdie. More recently, she’s become a freelance contributor to other publications including Vogue, Editorialist, and The Cut. Off the clock, you can find her clutching her cell phone as she's constantly scrolling through TikTok and The RealReal, in search of the next cool thing.