27 Chelsea Boots That Will Instantly Sharpen Your Look For Work & Play

If you haven’t heard of the legendary chelsea boot then your wardrobe has been missing out on one of the most reliable and stylish footwear options for men today.

The appeal of the chelsea boot is its ability to straddle both the casual and formal wardrobe. It works with a suit as well as it does with a pair of jeans with the only rule being that it should be well looked after to retain its polished appeal.

With an illustrious ancestry extending back to the British monarchy, it’s no surprise that they’re so well-loved today. A quick walk down memory lane shows that chelsea boots were originally intended as riding boots. The Beatles would eventually wear them on stage and it soon became the British mod movement of the 1960s.

With the resurgence of the chelsea boot in the men’s fashion space, there’s no shortage of materials, colours and price points to choose from. Thankfully we’re about to make your job easier with 27 of the best chelsea boots for men to buy right now. And once you’ve done that you can learn how to wear and style them.

Urban Outfitters Dress Chelsea Boot $89

Steve Madden Blackburn $100

Legends Tobacco Chelsea Boots $153

Steve Madden Dex Tan Suede $160

RUSH by Gordon Rush Gray $180

Astorflex Bitflex $185

Hunter Boots Original Refined Rubber Chelsea Boots $220

Shoe The Bear Dev Boots $228

Oliver Cabell Chelsea Boot | Lion $228

Clarks Clarkdale Gobi Boots $243

Scarosso Tobacco Suede Giancarlo Chelsea Boots $293

AllSaints Reiner Boot $295

AllSaints Rook Chelsea Boot $295

Frye Jones Chelsea $328

Scarosso Cooper Black Chelsea Boots $332

PS by Paul Smith Navy Suede Gerald Chelsea Boots $395

PS by Paul Smith Black Billy Zip Boot $395

Paul Evans The Wayne Low Cut Chelsea Boot – Chocolate $425

Paul Evans The Phoenix Chelsea Boot Coriander $450

Cheaney Brown Suede Godfrey Chelsea Boots $565

To Boot New York Shelby Suede Chelsea Boots $570

Tricker’s Lambourn Black Calf Leather Jodhpur Boots $645

Church’s Houston Leather Chelsea Boots $665

Common Projects Suede Chelsea Boots $680

R.M. Williams Comfort Turnout Boots $705

Barbanera Brown Suede Chelsea Boots $750

Crockett & Jones Chelsea Dark Brown Wax Calf Boot $992