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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

A neutral brown boot will go with any cropped pant.

The Statement Shoe

Vagabond Shoemakers Olivia Leather Boot

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

The Shiny Option

Sam Edelman Hilty Booties

Just a hit of The Matrix.

If Comfort Is Key

Dr. Martens Pascal Boot

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

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

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

The Unexpected Color

Vince Camuto Thelmin Bootie

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

The Punk Option

Boots with Buckles

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

The Mod Shoe

Photo: 18-08-16 Accessories AM2 B2 dylanremis W
Loeffler Randall Cooper Bootie

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

The Patent-Leather Option

Aeyde Leandra Patent Leather Ankle Boots

Brown patent leather is unexpected, but feels so now.

The Animal-Print Option

Diane von Furstenberg Dakota Leopard-Print Calf Hair Ankle Boots

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