Mens Chelsea Boots

Invest a pair of timeless men's Chelsea boots for day or night. Whatever the weather; simply slip on with some straight leg denims or spice up a suit with this classic style.

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26  items
Dr. Martens
2976 Chelsea Boots
Black Leather
£139.00
Dr. Martens
2976 Chelsea Boots
Gaucho Crazyhorse
£139.00
Dr. Martens
Graeme Chelsea Boot
Black
£129.00
Office
Bruno Chelsea Boots
Black Leather
£65.00
Office
Bruno Chelsea Boots
Brown Leather
£65.00
Timberland
Stormbuck Chelsea Boots
Dark Brown Leather
£60.00 £130.00 -54% SAVE 54%
Timberland
Larchmont Chelsea
Oakwood Nubuck Leather
£65.00 £110.00 -41% SAVE 41%
Timberland
Larchmont Chelsea Boots
Gaucho Saddleback
£65.00 £110.00 -41% SAVE 41%
Ted Baker
Hourb 2 Chelsea Boots
Black Leather
£65.00 £110.00 -41% SAVE 41%
Vagabond
Roy Chelsea Boots
Black Suede
£60.00 £110.00 -46% SAVE 46%
Vagabond
Johnny Chelsea Boots
Black
£65.00 £120.00 -46% SAVE 46%
Ted Baker
Lameth Chelsea Boots
Black Hi Shine Leather
£70.00 £125.00 -44% SAVE 44%
Hudson London
Adlington Chelsea Boots
Black Suede
£45.00 £70.00 -36% SAVE 36%
Office
Locked Chelsea Boots
Beige Suede
£30.00 £79.99 -63% SAVE 63%
Ask the Missus
Lightweight Chelsea Boots
Sand Suede
£25.00 £79.99 -69% SAVE 69%
Office
Barkley Chelsea Boots
Black Suede
£38.00 £59.00 -36% SAVE 36%
Office
Barkley Chelsea Boots
Grey Suede
£38.00 £59.00 -36% SAVE 36%
Office
Barkley Chelsea Boots
Tan Suede
£38.00 £59.00 -36% SAVE 36%
Office
Barkley Chelsea Boots
Chocolate Suede
£38.00 £59.00 -36% SAVE 36%
Office
Barkley Chelsea Boots
Brown Waxy Leather
£30.00 £59.00 -50% SAVE 50%
Office
Buster Chelsea Boots
Black Suede
£30.00 £59.00 -50% SAVE 50%
Office
Buster Chelsea Boots
Beige Suede
£25.00 £59.00 -58% SAVE 58%
Office
Barnaby Chelsea Boots
Black Suede
£17.00 £59.00 -72% SAVE 72%
Office
Blake Chelsea Boots
Tan Suede
£35.00 £59.00 -41% SAVE 41%
Office
Blake Chelsea Boots
Brown Leather
£35.00 £59.00 -41% SAVE 41%
Ted Baker
Travic Chelsea Boots
Brown
£65.00 £129.00 -50% SAVE 50%
Viewed 26 of 26 products
Looking for a staple shoe to carry you through the seasons? A pair of men's Chelsea boots are a must-have in every shoe collection. With a timeless design that strikes the perfect balance between comfort and smart-casual style, the Chelsea boot has been a popular choice for decades - and we get why! Ideal whether you're adding some sophistication to a laid-back outfit at the weekend or teaming them with a suit for a contemporary office look, a pair of black or brown leather Chelsea boots are a match made in heaven!