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

thigh high boot outfits


@georgia_3.0; Szymon Brzóska/The Style Stalker; @xbibigul; @chasingoutfits@noellevenegas

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.

thigh high boot outfits



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. Voilà!

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.

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.

thigh high boot outfits



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.

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.

thigh high boot outfits



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.

thigh high boot outfits



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.

thigh high boot outfits



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.

thigh high boot outfits



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.

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. 

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).

thigh high boot outfits



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.

thigh high boot outfits



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).

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.

thigh high boot outfits


Szymon Brzóska/The Style Stalker

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.

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.

Re-create this look:
Shop more thigh-high boots:

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

Sparkly pink boots? Yes, please. 

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

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

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

Imagine these boots with a pleated skirt and sweater.

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