Thigh-High Boot Outfit Ideas Anyone Can Wear for Fall

Just go for it.

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Christian VierigGetty Images

The thigh-high boot is a dramatic shoe. There's something provocative, but also uber stylish, about the silhouette. Julia Roberts in Pretty Woman rocked them amazingly well—though, if pre-makeover Vivian Ward isn't exactly the vibe you're going for on a Monday morning, we understand. We've found seven work- and weekend-appropriate ways to wear the shoe without shoving you completely out of your comfort zone. Thigh-high boots can look elegant, not tawdry, when styled with the right fall/winter pieces. 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.

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1 A Leather Skirt + Thigh-High Boots
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Design by Morgan McMullenGetty Images

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 at the office or on a date.

Shop the pieces: 1. Max Mara coat, $2,750; 2. Ganni sweater, $264; 3. Sam Edelman boots, $240; 4. Alexa Chung leather skirt, $269; 5. Mansur Gavriel x Calder Circle bag, $795

2 Denim Biker Shorts + Thigh-High Boots
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Design by Morgan McMullenGetty Images

Meet your thigh-high boots halfway with a pair of biker shorts. The denim variety adds more intrigue than a pair of blue jeans, while a cropped shearling bomber jacket ensures you're properly covered in the cooler weather. The ensemble says sporty yet stylish, though you won't be running around any fields in those boots. Scuff marks are the bane of our existence.

Shop the pieces: 1. 3.1 Phillip Lim bomber jacket, $595; 2. AG Jeans denim shorts, $126; 3. Stuart Weitzman boots, $850; 4. Brahmin bucket bag, $265

3 A Mini Dress + Thigh-High Boots
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Design by Morgan McMullenGetty Images

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 the fluffiest, furry coat. The trick to pulling off this outfit is covering up as much as possible. And, calling a cab to get to and from events. (You won't see me in this outfit on a grocery store run this winter.)

Shop the pieces: 1. Nanushka coat, $850; 2. Isabel Marant dress, $645; 3. Casadei thigh-high boots, $1,325; 4. Cult Gaia tote, $300

4 A Snakeskin Dress + Snakeskin Thigh-High Boots
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Design by Morgan McMullenGetty Images

Double down on one of fall/winter's most popular trends: animal print. Start with a snakeskin thigh-high boot and match your outerwear to your shoes. If you're looking for a two-for-one, unbutton this dress and wear it as a coat over another shift. Or, button up (leave a few undone at the bottom to show off your shoes) and top with a heavier coat.

Shop the pieces: 1. Stand Studio dress, $960; 2. Zimmermann polka dot dress, $233; 3. Steve Madden boots, $110; 4. Tara Zadeh leather clutch, $289

5 A Cape + Thigh-High Boots
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Design by Morgan McMullenGetty Images

The cool alternative to a trench coat in 2019? A cape. You're probably wondering how to wear this without it slipping completely off your shoulders—Miu Miu has the answer. The brand's utilitarian cape comes with two arm holes for you to slide into and has buttons all down the front for secure fastening. Since the outerwear is so special, keep the rest of your pieces simple, including your thigh-high boots. A classic brown block heeled option works perfectly.

Shop the pieces: 1. Miu Miu cape, $2,970; 2. Everlane sweater, $95; 3. Madewell jeans, $128; 4. Splendid boots, $169; 5. MCM pouch, $375

6 A Shirtdress + Thigh-High Boots
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Design by Morgan McMullenGetty Images

Thigh-high boots can look prim and proper, rather than super casual, when worn with a shirtdress and blazer. Take a note from Chiara Ferragni who balanced out the boldness of her casual red boots with some tailored pieces. These small changes also took the outfit from Superwoman costume to power woman on the move. Though, if you wanted to be Superwoman on October 31st, here's half of your outfit already.

Shop the pieces: 1. AllSaints blazer, $198; 2. Anna Sui sunglasses, $149; 3. Sies Marjan shirtdress, $895; 4. GUESS Inc. red boot, $169; 5. Botkier crossbody bag, $198

7 An Oversize Sweater + Thigh-High Boots
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Design by Morgan McMullenGetty Images

A sweater dress and thigh-high boot is a classic combination. To keep it feeling fresh and new this season, opt for a luxurious Fendi pair—everyone's rocking the brand right now—and Aritzia's newest super puff outerwear. The iconic footwear instantly elevates any basic outfit to a more fabulous version of itself. For more ideas on how to style this thigh-high boot: wear it with jeans, wear it under a long dress, wear it with tights, etc etc.

Shop the pieces: 1. Aritzia long puffer coat, $298; 2. Vera Wang sunglasses, $275; 3. Topshop sweater dress, $75; 4. Fendi thigh-high boots, $1,590; 5. Marge Sherwood slim bag, $245

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