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.
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.
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.
WHO: Yatri Pabari
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.
WHO: Bianca Valle
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.
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.
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.
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).
WHO: Yoyo Cao
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.
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.
Photo:Szymon Brzóska/The Style Stalker
WHO: Julia Comil
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.
These boots would look so good with this Paco Rabanne Jacquard-Knit Turtleneck Maxi Dress ($790).
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.
These would go perfectly with your skinny jeans.
White boots are never a bad idea.
Hello, suede boots of my dreams.
You can wear these all winter.
Talk about a statement boot.
I'm pretty sure Rihanna would wear these.
These boots are a timeless staple.