How To Wear Chelsea Boots

As with any menswear item considered a heritage piece, you’ll need to tread carefully when styling to avoid going into turbo toff mode. Good, advise for going more rockstar Wear Chelsea boots casually with jeans, a white T-shirt and a thrown-on shirt.

If you’re looking to sharpen up your act, however, both what you wear and the boot’s ankle height come into play. A taller ankle height is very on-trend and adds a smarter feel for a sharper look. These look great when worn with slim jeans, a crisp Oxford shirt, and a smart cool coat.

As for where you’ll find the best, here are 20 brands delivering on style, substance, and a little more style.