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How to Wear Boots in the Warmest (and Chicest) Way This Winter

Author

Ava Hudson

Updated on March 29, 2026

Snow boots are the unsung hero of wintertime. They're reliable, comfortable, and dependable—but not many people see them as stylish, and that's a huge oversight. Sure, your favorite pair of duck boots may not seem fashionable at first, but they absolutely work when they're paired with the right outfit. In fact, once you've figured out how to wear snow boots with style, you won't want to put on another shoe ever again. Even during summertime. Catch me this Memorial Day at the pool wearing a bathing suit and duck boots.

Okay, I'm kidding. We'll most likely retire our winter boots come April, which will be sad because they've never looked better. Still not convinced? Here's what inspired me to change up how I wear them:

Pair with skinny jeans or leggings.

Like Aubrey Plaza does in this photo. This helps show off the color and details of your boot. Wear like this if you have a pair in an electric shade.

Getty Images

Debra Messing achieves a similar look in the photo, below.

Getty Images