The thigh-high boot is a dramatic shoe. (opens in new tab)There's something provocative, but also stylish, about the silhouette. Julia Roberts in Pretty Woman rocked them amazingly well—but if pre-makeover Vivian Ward isn't exactly the vibe you're going for on a Monday morning, nay, even a Saturday night, we understand. We've found 17 work- and weekend-appropriate ways to wear the shoe without shoving you completely out of your comfort zone. (The easiest outfit to throw together? Your favorite top, jeans, and the killer leg-skimming boots.) Thigh-high styles can look elegant, not tawdry, when styled with the right fall/winter pieces. (And if you need to stock up on said fall items, here you go (opens in new tab).) Using a little street style inspo, below, we'll show you how to put items you already own together for a cohesive, fashion girl-approved ensemble. We even provided similar boot options to shop just in case you don't have a pair, or need a new one.
Thigh-high boots can look prim and proper, rather than super casual, when worn with a blazer or tailored jacket. Take a note from this street style star and go for a monochromatic color scheme. These small changes took the outfit from plain to power woman on the move.
Yeezy stiletto boots, $378 SHOP IT (opens in new tab)
Animal Print Galore
Sometimes you want your thigh-high boots to make a statement and a cow print pair fulfills this job. Let the boot have the spotlight by keeping everything else neutral. However, if you do want to take that extra style step, add in a contrasting animal print through a small accessory.
Giuseppe Zanotti boots, $1,125 SHOP IT (opens in new tab)
Thigh-high boots don’t have to be strictly lace-ups and skinny column silhouettes. They can have a cowboy-inspired feel. To keep you outfit from feeling like the wild wild west, style with a fitted top and a trendy handbag.
Missy Empire, $55 SHOP IT (opens in new tab)
Meet your thigh-high boots halfway with a pair of belted wool or leather shorts. The bottom adds more intrigue than a pair of blue jeans and allows you to extend the shelf life of your favorite summer bottoms.
ASOS thigh-high boots, $36 SHOP IT (opens in new tab)
Let It Shine
Gold thigh-high boots are for the brave, and if that sounds like you then there’s nothing stopping you from rocking a pair 24/7. Keep your outfit bold and cool while also accessorizing with some gold accented pieces like a belt.
Paris Texas boots, $398 SHOP IT (opens in new tab)
Sweaters, jeans, and boots is an easy combo, but here's another quick idea for ya: sweater, leather dress, and thigh-high boots. The outfit is great for the beginning days of fall to keep you warm and cool at the same time.
Le Silla boots, $873 SHOP IT (opens in new tab)
Dreaming About Summer
You're not ready to part with your summer mini dress. The solution? Throw on a pair of thigh-high boots, maybe some tights, and then cocoon yourself into a coat. The trick to pulling off this outfit is covering up as much as possible. And, calling a cab to get to and from locations.
Victoria Beckham boots, $930 SHOP IT (opens in new tab)
An Everyday Look
If you're just warming up to the idea of wearing thigh-high boots, they do make you feel invincible and cool, keep it simple with jeans, your favorite top, and a furry coat. You'll feel dressed up without completely leaving your fashion comfort zone.
Kate Spade New York boots, $299 SHOP IT (opens in new tab)
Prints, Prints, and More Prints
Remember when you couldn't care less about mixing all sorts of wacky prints as a child? Pay homage to that feeling by opting to style your thigh-high animal boots with some sweet florals. Take joy in dressing up for yourself, not the critics.
Steve Madden boots, $120 SHOP IT (opens in new tab)
Cool and Casual
Take a note from this street style star and have your thigh-high boots peek out from underneath a leather skirt. Color coordinate the two pieces for a uniform bottom, then add a little color on top with a festive sweater. This combination looks smart and put together, so feel free to show off the look via Zoom or on a date.
Prada thigh-high boots, $940 SHOP IT (opens in new tab)
Dress It Up
My personal go-to for wearing thigh-high boots is underneath a flowing maxi dress. Even better is if there is a side slit that allows you to show off your footwear with every step you take.
Fendi thigh-high boots, $1,490 SHOP IT (opens in new tab)
Whether or not you've watched The Matrix, you're probably all too familiar with the black trench coats from the film. Take things up a notch with a pair of glossy red thigh-high boots and a vintage band tee.
Saint Laurent boots, $1,595 SHOP IT (opens in new tab)
Putting Up With Plaid
Animal print not your thing? That's totally fair. Select a pair of boots with the plaid treatment instead. This classic pattern goes well with something as simple as a denim skirt and tee while adding that extra-ness to your everyday look.
Plaid boots, $62 SHOP IT (opens in new tab)
Denim on Denim
One of my favorite denim on denim...on denim looks. The key is to keep your pieces in the same color family or as a complete set and let your boots stand out, not fade into your outfit.
Le Silla boots, $1,196 SHOP IT (opens in new tab)
When in doubt, throw on a beige sweater, cream-colored jeans, and your thigh-high western boots. The outfit is cute and not overly flashy, if you err on the more minimalist side.
Public Desire boot, $56 SHOP IT (opens in new tab)
If none of the thigh-high boot options thus far has appealed to your fashion senses, here's a pair that might change your mind. This transparent lace-up footwear will definitely make your head, and a few others, turn.
Pretty Little Thing, $58 SHOP IT (opens in new tab)
Don't be afraid to pile on the color if you're wearing red thigh-high boots. It's a sure sign that you're confident in your style and in your own skin. A total street style moment.
Petar Petrov, $529 SHOP IT (opens in new tab)
Marina Liao is the former fashion news editor at MarieClaire.com, where she covered celebrity style (from Meghan Markle to Katie Holmes), fashion trends, and shopping advice, plus conducted original interviews with industry insiders. She's also had many opportunities to write content in other areas such as beauty, food, tech, and even home. Her previous fashion stints include POPSUGAR and Cosmopolitan.
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