A Chelsea boot is the Chukka boot’s more sophisticated cousin. They’ve got a modern yet timeless styling that makes them more versatile than a classic Chukka. Chelsea boots tend to have a sleeker look, and the slimmer shaft allows you to wear them with more pants and jean silhouettes than you can with a Chukka boot.

Read on to see our tips on how to wear Chelsea boots.  

T-Shirt Guide


When it comes to jeans and boots, you’ve got two options: cuff your jean above the top of the boot, or pull down the leg of the jean over the top of the boot. While a slim fit or skinny jean is often too slim to pull over a Chukka or lace-up boot, they will often work with a slimmer Chelsea boot. Once you’ve found a pair of denim that works with your boots, you’ve got a versatile anchor for a multitude of outfit combos. Try these pairings:

  • T-shirt and bomber jacket
  • Casual button-up and V-neck sweater
  • Plaid flannel and slim-line vest.
  • Dress shirt and blazer

How to Wear Navy and Black Together


Chelsea boots are also a terrific work shoe. In inclement weather, they’ll help you maintain a professional look and keep you warm. Lightweight styles in tan hues are also great options to sport in warmer weather. Did you know you can wear Chelsea boots with a suit? Just make sure they’re a dressier Chelsea and that you’ve given them a good shine. Try these combos for work:

  • Chinos and a button-up in a seasonal hue
  • Your go-to suit, dress shirt and tie
  • Neutral dress pants, button-up and blazer
  • Printed button-up and sweater vest


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