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 outfit ideas can feel as taxing as slipping them off at the end of a long day. Not to mention while they may elicit “step on me” feelings, they’re not exactly the easiest boots 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 found existential dread coming on upon reading that last sentence, we’re 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 previous seasons—you just have to keep scrolling to see for yourself.
WHO: Noelle Venegas
WHAT: Shoedazzle thigh-high boots
WEAR: Turtleneck sweater dress with a slit, 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 ones or another bold pair, be sure to pair 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: Oversized button-up dress, sweater, thigh-high boots.
Who said you need to purchase a whole new look to suit your boots? Just pull out your oversized white button-up, layer a sweater over, and slip into those thigh-high boots, and voila!
Pair these boots with
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.
Wear these boots with Terra & Sky’s V-Neck Sweater Dress.
WHO: Oriane Adjibi
WHAT: Primark Sweater and Black Cycling Shorts ($4).
WEAR: turtleneck, biker shorts, thigh-high boots.
Consider this a public service announcement: 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 oversized turtleneck for a casual yet fresh take on styling your boots.
WEAR: bolero, knit bralette, sweats, thigh-high boots.
Want another informal way to style your thigh-high boots? Try pairing them with sweat pants. Yes, you read that right—tuck your favorite joggers under your thigh-high boots and throw on a knit bralette and bolero sweater for a cozy look that just so happens also to let you wear your shoes. 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, without fail, works every time.
WHO: Yatri Pabari
WEAR: Turtleneck, sweater vest, Bermuda shorts, thigh-high boots.
If you can’t imagine wearing a dress during the winter but also struggle to wear your thigh-high boots over denim or pants, then we 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, 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 Bermuda cut for your favorite blue jeans shorts and you’ve got an equally chic look. Pro tip: this look is all about the boots being the focus of the look, so don’t be afraid to opt for your boldest pair of thigh-high booties.
Strict budget? You may like these ASOS Keisha Premium Stretch Over-The-Knee Boots ($119).
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, thigh-high boots.
You don’t have to miss out on wearing thigh-high boot outfits if you live in a warmer climate—in fact, you can get creative with your look by wearing them with fewer layers. Pair your boots with either a fringe coat or fleece jacket (based on the temperature) with a simple tank and mini-skirt for a warm-weather friendly look that allows you to wear your boots without overheating.
Pair these boots with IRO’s Cocha Shacket ($600).
WHO: Morgan Fitzpatrick
WHAT: Public Desire Brandy Stone Western Block Heeled Knee High Boots ($75); MTF Label Bag.
WEAR: Oversized blazer, thigh-high boots, micro handbag.
If you live in a warmer climate, then this thigh-high boot outfit idea is also for you. Wear your favorite oversized blazer as a dress, and slip into your thigh-high boots for a look that rivals your city’s heat.
Pair these thigh-high boots with this Altaire Triangle Knot Bag ($425).
WHO: Maggie McCormack
WHAT: Sororité vintage blazer; Nasty Gal Belt; Simmi Shoes.
WEAR: Oversized 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 oversized blazer to add another layer of warmth to your outfit.
WEAR: Matching tonal sweater and slip skirt, with mismatch 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 you didn’t break the bank on your look).
WHO: Yoyo Cao
WEAR: Oversized statement coat, 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 oversized coat if all else fails for a look that’s precisely on-trend for the season.
WHAT: Lespecs Sunglasses; Zara Faux Leather Oversized Blazer ($70).
WEAR: Black mini dress, leather blazer, thigh-high boots.
The other staple outwear 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. We 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: Oversized 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 looks far more polished than it actually is.
Photo:Szymon Brzóska/The Style Stalker
WHO: Julia Comil
WEAR: holiday sweater, leather skirt, shoulder bag, 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.
Pair these boots with our Faux Leather Circle Midi Skirt ($35).
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, 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 for season after season. Furthermore, they’re a style that, while it takes a bit more creativity in terms of coming up with outfit ideas, you won’t regret wearing.
The season’s trendiest thigh-high boots also happen to be flats—which we’re very much here for.
Fun and affordable? Don’t mind if I do.
No lie; I allocate at least twenty minutes a week to stare at these boots.
The tweed detailing on these thigh-high boots is everything.
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 boots are a timeless staple.