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
The Statement Shoe
This would look great as part of a monochromatic red outfit.
The Shiny Option
If Comfort Is Key
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
Western-inspired dressing has been everywhere lately, but these are subtle enough to last for more than one season.
The Party Shoe
Dress these shoes down with a pair of jeans and a T-shirt. They speak for themselves.
The Unexpected Color
The Punk Option
The Mod Shoe
A sleek way to embrace your inner go-go dancer.
The Patent-Leather Option
The Animal-Print Option
A little bit Victorian thanks to the lace-up front, but very large bit stylish.
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