It works with any timeless beige trench and brown suede boots, or even a head-to-toe leather look complete with a longline black leather trench and platform Chelsea boots.

I’m sharing a roundup of ways to style Chelsea boots that will help you elevate this classic piece and give it a fresh, updated look for any occasion.

Reese Witherspoon wore a pair of high-rise bootcut jeans at Hello Sunshine’s Shine Away event in Los Angeles. These flared-leg pants are great for fall and winter because they cover bulky boots ...

They play especially well with another closet staple: denim. Not as soft as a beige sandal, nor as fierce as a black heel, ...

I styled them with jeans first and a pair of dress slacks the second time I wore them—they are versatile and sleek.” Cole Haan Zerogrand Waterproof Chelsea Boots in Pavement-Black, $100 (was ...

Girls who pass by are clad in skinny blue jeans, khaki parkas and, you guessed it, Chelsea boots. No shoe has oscillated between cool and uncool quite like the Chelsea boot.

The best Chelsea boots for women are practical yet stylish. Here are the top pairs to buy, according to our in-depth review, and advice from a fashion stylist.

The best women’s Chelsea boots are practical and stylish, including special interpretations from Dorothee Schumacher, Prada, and more brands. Shop them here.

Chelsea boots are the perfect transitional shoe from spring to summer. Here’s how to wear Chelsea boots in 2025.