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These Are the Best Boots to Wear With Cropped Pants

Photo: Courtesy of the Retailer

Almost every pair of pants is at least a little bit cropped now, whether a Sabrina-style ankle-revealing crop or the wide-leg crop popularized by Jesse Kamm and Everlane. This presents a challenge: What shoes can you wear with them in cold weather that are nicer than a sneaker and socks? An ankle boot or a heel leaves a bit too much lower shin exposed to the frigid air. The key, then, is a bootie with at least a six-inch shaft, so there’s not a huge gap between the hem of the pants and the top of the boot. The shaft should also be somewhat tight up your leg. And voilà! The perfect way to wear your cropped pants into the cold winter months.

The Starter Boot

ASOS DESIGN Elexis Leather Ankle Sock Boots
$87 at ASOS

A neutral brown boot will go with any cropped pant.

The Statement Shoe

Vagabond Shoemakers Olivia Leather Boot
$160 at Urban Outfitters

This would look great as part of a monochromatic red outfit.

The Shiny Option

Sam Edelman Hilty Booties
$160 at Shopbop

Just a hit of The Matrix.

If Comfort Is Key

Dr. Martens Pascal Boot
$140 at Nordstrom

You don’t have to wear heels to make the outfit work. A trusty pair of Docs will do the trick.

If You’re Buying Into the Western Trend

Frye Sacha Chelsea Booties
$298 at Shopbop

Western-inspired dressing has been everywhere lately, but these are subtle enough to last for more than one season.

The Party Shoe

Rebecca Minkoff Sayres Glittery Sock Boot
$198 at Saks Fifth Avenue

Dress these shoes down with a pair of jeans and a T-shirt. They speak for themselves.

The Unexpected Color

Vince Camuto Thelmin Bootie
$140 at Nordstrom

Teal is a modern way to add color into a look.

The Punk Option

Boots with Buckles
$70 at H&M

Nothing like four large buckles to add a little bit of edge.

The Mod Shoe

Loeffler Randall Cooper Bootie
Photo: 18-08-16 Accessories AM2 B2 dylanremis W
Loeffler Randall Cooper Bootie
$450 at Shopbop

A sleek way to embrace your inner go-go dancer.

The Patent-Leather Option

Aeyde Leandra Patent Leather Ankle Boots
$385 at Net-a-Porter

Brown patent leather is unexpected, but feels so now.

The Animal-Print Option

Diane von Furstenberg Dakota Leopard-Print Calf Hair Ankle Boots
$400 at Net-a-Porter

A little bit Victorian thanks to the lace-up front, but very large bit stylish.

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These Are the Best Boots to Wear With Cropped Pants