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There’s no arguing that ankle boots are killing it this season, but there’s another set of steppers that are doing equally as well, sartorially speaking: over-the-knee boots. These high-reaching numbers aren’t exactly for the non-adventurous — they make quite a statement — but they can totally work in just about any wardrobe. They’re BFFs with slim cut trousers, mini dresses and asymmetrically cut midi skirts, plus they instantly add a fashion-forward edge to simple separates. The key to keeping them feeling fresh each season? Pairing them up with hot-right-now colors and silhouettes. Here are three ways to wear these eye-catching kicks right now.

How to Wear Over-the-Knee Boots at Work

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Those tailored work pants are about to get a whole lot more interesting with over-the-knee boots thrown into the mix. To create a look that fuses equal parts polish and style, add in a button-down in soft flannel fabric layered underneath a rich, autumnally hued blazer. Bonus points for long-line styles. Complete the getup with smart tech accessories and a bright carry-all.

Oasis Over the Knee Block Heel Boots ($171) + Mango Combi Print Trousers ($70), Zara Long Blazer With Flap Pockets ($150), Reversible Vegan Leather Tote Bag ($59), Madewell Flannel Sunday Shirt ($88), Ringly Bluetooth Smart Ring ($260)

How to Wear Over-the-Knee Boots on a Night Out

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Cold-weather dressing is all about balance. Keeping warm and cozy means lots of layering, but that doesn’t have to mean frumpy and bulky. Over-the-knee boots keep legs covered and looking chic, while a turtleneck and printed mini-dress combo feels sophisticated and incredibly of the moment. Playful accessories like a colorful faux fur coat and metallic clutch infuse the look with personality and drive it well into par-tayyy territory.

Oasis Over the Knee Block Heel Boots ($171) + Topshop Multi-Colored Faux Fur Coat ($170), Selected Femme White Cathy Shift Dress ($100), J.Crew Tippi Mockneck Sweater ($70), ASOS Harmonic Zip Top Clutch Bag ($33), BCBG Double-Wrap Whipstitch Belt ($68), Joomi Lim Lost Innocence Spike and Chain Earrings ($60), Bobbi Brown Long-Wear Gel Eyeliner ($25), Christian Louboutin Nail Color ($50)

How to Wear Over-the-Knee Boots on the Weekend

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Off-duty isn’t all joggers and sweats. There is some serious style to be had during those off-the-clock hours, and statement steppers are good place to start. Pair them up with mist-hued skinny jeans and an oversized, grid-check top for the ultimate fusion of casual and cool. Shearling introduces a rustic edge to the look, while funky shades and colorful, high-shine accessories keep it real.

Oasis Over the Knee Block Heel Boots ($171) + Mother Denim The Looker Ankle Fray Jeans ($180), A Common Space Plaid Fringe Shirt Dress ($68), Topshop Faux Shearling Car Coat ($150), Friends With Benefits Taylor Headphones ($200), Quay Australia Westend Girl ($50), Furla Metropolis Shoulder Bag ($498), Olympus Pen E-PL7 Camera ($500)

What pieces in your closet deserve more attention, but stump your style game? Tell us about your trickiest wear-again garments in the comments below and we might feature them in our next Style Resolutions post!

Libby MacCarthy
Libby MacCarthy is an urban planner turned writer with a love (bordering on unhealthy obsession) of all things fashion and beauty related. She lives for perfectly brewed coffee, farmer's markets, dinner parties and perusing impeccably designed boutiques. When she's not on the hunt for the latest trends, you'll likely find her plotting her next adventure or nose deep in a book. Libby currently splits her time between the East Coast and her adopted home of France. Follow her daily adventures on Instagram.