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

These kicks were made for super styling.

Best Men's Chelsea Boots

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 UO Dress Chelsea Boot
Urban Outfitters Dress Chelsea Boot $89
Steve Madden Blackburn
Steve Madden Blackburn $100
Legends Tobacco Chelsea Boots
Legends Tobacco Chelsea Boots $153
Steve Madden Dex Tan Suede
Steve Madden Dex Tan Suede $160
RUSH by Gordon Rush Gray
RUSH by Gordon Rush Gray $180
Huckberry Astorflex Bitflex
Astorflex Bitflex $185
Hunter Boots Original Refined Rubber Chelsea Boots
Hunter Boots Original Refined Rubber Chelsea Boots $220
Shoe The Bear Dev Boots
Shoe The Bear Dev Boots $228
Oliver Cabell Chelsea Boot Lion
Oliver Cabell Chelsea Boot | Lion $228
Clarks Clarkdale Gobi Boots
Clarks Clarkdale Gobi Boots $243
Scarosso Tobacco Suede Giancarlo Chelsea Boots
Scarosso Tobacco Suede Giancarlo Chelsea Boots $293
AllSaints Reiner Boot
AllSaints Reiner Boot $295
AllSaints Rook Chelsea Boot
AllSaints Rook Chelsea Boot $295
Frye Jones Chelsea
Frye Jones Chelsea $328
Scarosso Cooper Black Chelsea Boots
Scarosso Cooper Black Chelsea Boots $332
PS by Paul Smith Navy Suede Gerald Chelsea Boots
PS by Paul Smith Navy Suede Gerald Chelsea Boots $395
PS by Paul Smith Black Billy Zip Boots
PS by Paul Smith Black Billy Zip Boot $395
Paul Evans The Wayne Low Cut Chelsea Boot - Chocolate
Paul Evans The Wayne Low Cut Chelsea Boot – Chocolate $425
Paul Evans The Wayne Low Cut Chelsea Boot - Chocolate
Paul Evans The Phoenix Chelsea Boot Coriander $450
Cheaney Brown Suede Godfrey Chelsea Boots
Cheaney Brown Suede Godfrey Chelsea Boots $565
To Boot New York Shelby Suede Chelsea Boots
To Boot New York Shelby Suede Chelsea Boots $570
Tricker's Lambourn Black Calf Leather Jodhpur Boots
Tricker’s Lambourn Black Calf Leather Jodhpur Boots $645
Church's Houston Leather Chelsea Boots
Church’s Houston Leather Chelsea Boots $665
Common Projects Suede Chelsea Boots
Common Projects Suede Chelsea Boots $680
R.M. Williams Comfort Turnout Boots
R.M. Williams Comfort Turnout Boots $705
Barbanera Brown Suede Chelsea Boots
Barbanera Brown Suede Chelsea Boots $750
Crockett & Jones Chelsea Dark Brown Wax Calf Boot
Crockett & Jones Chelsea Dark Brown Wax Calf Boot $992

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