Elastic sides are the feature that makes a Chelsea boot a Chelsea boot. To fit the classic profile, a Chelsea boot should also hit a little above the ankle, come with a pull tab in the back ...

The Caslon Miller Lug Chelsea Boot is currently on sale at Nordstrom ... brown chestnut, olive, and beige sand that are all neutral enough to pair with jeans, trousers, skirts, and even dresses.

Learn more! Regardless, rich moms near and far have taken on the trend, pairing Chelsea boots with everything from jeans and leather pants to dresses and skirts. It’s a casual yet ultra-classy ...