7 Ways to Wear Cropped Pants in the Winter

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If you’ve caught on to the trend of cropped pants in January and fear your ankles will freeze while wearing them in the cold, worry not — the right footwear will help you pull off the look and keep you warm while you’re at it.

For starters, make sure your boots, closed-toe heels, or sneakers complement the hem length. When wearing sneakers or closed-toe shoes, a couple inches of ankle space looks chic and breaks up the pattern. If you’re trying boots, make sure your pants reach the top of the shaft so you don’t look like you’re wearing something too short for your legs. Here are seven easy ways to go short.

Flared Cropped Pants

These cotton flared cropped pants by Awake take a chic turn when paired with white ankle boots (arguably the coolest footwear of the season). A bright sweater balances the dark shade of the pants.

Awake pants, $421 at Matches Fashion, Tibi Sweater, $262 at IfChic, MM6 Maison Margiela Boots, $560 at SSENSE.

Crepe Slim Cropped Pants

Switch up your black-pants routine with cropped black culottes. Paired with a fancy Saint Laurent blouse and suede Chloe platforms (and tights obviously), they’re also a nice alternative to the cocktail dress.

Saint Laurent Blouse, $1,194 at Farfetch, Chloe Sandals, $864 at Matches Fashion, Aritzia Culottes, $125 at Aritzia.

Denim Cropped Pants

The slight flare on Frame’s cropped jeans adds dimension without making them look dated. Embrace the sporty look with a track sweater and fresh pair of Nikes.

Frame Jeans, $138 at Matches Fashion, Nike Sneakers, $125 at Nike, Tory Sport Pullover, $250 at Tory Sport.

Embellished Cropped Pants

Let Marc Jacobs’s sequined, cropped army pants speak for themselves by wearing a plain black bodysuit and black boots. The pants will still be the focal point, but the solid colors will break up the busy pattern.

Madewell Bodysuit, $30 at Madewell, Marc Jacobs Pants, $695 at Net-A-Porter, Gianvito Rossi Boots, $995 at Fwrd.

Satin Cropped Pants

Satin may not be as warm as other materials, but it is one of the classiest. Stay toasty in these pants by wearing nude tights underneath. When paired with a simple nude suede shoe and Proenza Schouler’s bell-sleeve blouse, this outfit is a sleek alternative to everyday work wear.

Proenza Schouler Top, $510 at Matches Fashion, Tibi Pants, $425 at Net-A-Porter, Gianvito Rossi Heels, $675 at Barneys New York.

Leather Cropped Pants

These cropped J Brand leather pants have a layer of stretch-coated denim underneath, so they won’t stick to your legs. Wear them with a bright oversized sweater and Chelsea boots.

J Brand Pants, $230 at Net-A-Porter, Zara Sweater, $50 at Zara, Pola Boots, $98 at Urban Outfitters.

Jersey Cropped Pants

If you want to try the track-pants trend, try wearing Gucci’s version with a metallic ankle boot and a cozy thermal.

Gucci pants, $950 at Gucci, Saint Laurent boots, $995 at Matches Fashion, Topshop sweater, $55 at Topshop.

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7 Ways to Wear Cropped Pants in the Winter