The thigh-high boot is a dramatic shoe. 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.) 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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