Chelsea Boots

Arthur Knight Shoes are proud to offer the largest selection of elasticated slip-on Chelsea Boots for men with over 100 styles to choose from by famous designer brands. Originating in the 1800s as a type of riding boot known as jodhpur boots, the Chelsea (also known as ‘ankle boots’) was first worn by royalty after being designed and made by J. Sparkes-Hall. Created for both men and women, Queen Victoria was known to wear a pair of Chelsea boots around the palace grounds. Of course, it wasn’t long before the design was highly sought after across the country and beyond. The Chelsea’s boot classic markings include rear pull tabs and side gussets for a slip-on and slip-off motion, an invention that was only possible following the creation of stretchy, vulcanised rubber.

The Chelsea boot for men became hugely popular again in the 1960s when famous musicians such as The Beatles wore them. The most distinctive feature of the men’s Chelsea Boot style is its elastic siding, called a gusset, running from the heel to the top of the boot. They are renowned for their timeless appearance and continue to be a bestselling style worldwide.

Compared with laced shoes and boots, this style has the advantage of having both an easy slip-on nature (hence the sewn finger-pull-loop at the back of the Chelsea Boots) as well as a very ‘clean’ appearance on the foot as a result of the whole leather cut. For this reason, Chelseas are typically very versatile and can be worn in the workplace, at social functions or just as an everyday boot. It also supports the ankle area more than other styles, which some of our customers have found provides additional comfort during wear. All Chelsea boots offered by Arthur Knight have robust, hard wearing soles and comfortable interior lining, as well as supportive footbeds, ensuring that your foot can breathe but remains snug and secure while you’re out walking. When cared for properly, there is no reason a well-made Chelsea can’t last you for many years to come.

If you are looking for a classic, round toe Chelsea, we might direct you to the incredible range offered by John White. For a more flamboyant look, you could check out our offering by Jeffrey West. Chelsea boots come in a huge number of variations and can include pointed, round or square toes, various side gusset contrast colouring and sometimes both front and rear pull tabs for a more distinctive look.

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  1. Exclusive Jeffery West Black Polished Skull Chelsea Boots
    Exclusive Jeffery West Black Polished Skull Chelsea Boots
    Jeffery West Shoes
    $281.65
    sizes
    available sizes: US7, US8, US9, US10, US11, US12, US13
  2. Brown Suede Barbour Farsley Cheslea Boot Red Elastic
    Brown Suede Barbour Farsley Cheslea Boot Red Elastic
    Barbour Shoes
    $155.89
    sizes
    available sizes: US8, US10, US11, US12, US13
  3. Black & Grey Mens 1452 Blundstone Chelsea Boots
    Black & Grey Mens 1452 Blundstone Chelsea Boots
    Blundstone Boots
    $149.34
    sizes
    available sizes: US9, US10, US11, US12
  4. Burgundy & Waxy Brown Chelsea Boot Brogues by Anatomic
    Burgundy & Waxy Brown Chelsea Boot Brogues by Anatomic
    Anatomic
    $170.23
    sizes
    available sizes: US9, US10, US11, US12, US13
  5. Jeffery West Dark Burgundy Red Elastic Chelsea Boots
    Jeffery West Dark Burgundy Red Elastic Chelsea Boots
    Jeffery West Shoes
    Special Price $294.75 Regular Price $432.30
    sizes
    available sizes: US8½, US9½, US10, US12
  6. Matt Black Nubuck Leather Bugatti Beatle Boots for Men
    Matt Black Nubuck Leather Bugatti Beatle Boots for Men
    Bugatti Mens Shoes
    Special Price $91.63 Regular Price $117.83
    sizes
    available sizes: US8, US9, US10, US11
  7. Black Suede & Burgundy Oliver Sweeney Chelsea Boots
    Black Suede & Burgundy Oliver Sweeney Chelsea Boots
    Oliver Sweeney
    $196.43
    sizes
    available sizes: US9, US11
  8. Double Wingtip Brown Jeffery West Chelsea Brogues
    Double Wingtip Brown Jeffery West Chelsea Brogues
    Jeffery West Shoes
    $288.20
    sizes
    available sizes: US8, US9, US12
  9. Navy Blue John White Slip on Chelsea Boots
    Navy Blue John White Slip on Chelsea Boots
    John White
    $176.85
    sizes
    available sizes: US8, US9, US11, US12
  10. Mid Brown Suede Round Toe John White Chelsea Boots
    Mid Brown Suede Round Toe John White Chelsea Boots
    John White
    Special Price $124.45 Regular Price $176.85
    sizes
    available sizes: US8, US9, US10, US11, US12
  11. English Jeffery West Chelsea Brogues in Black Polished
    English Jeffery West Chelsea Brogues in Black Polished
    Jeffery West Shoes
    $425.75
    sizes
    available sizes: US8, US9, US11, US12
  12. Fire Red Jeffery West Chelsea Brogues in Black
    Fire Red Jeffery West Chelsea Brogues in Black
    Jeffery West Shoes
    $314.40
    sizes
    available sizes: US8, US12
  13. Barbour Farsley Waxy Tan Chelsea Boots
    Barbour Farsley Waxy Tan Chelsea Boots
    Barbour Shoes
    $155.89
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  14. Navy Blue Tommy Hilfiger Stream Rubber Chelsea Welly
    Navy Blue Tommy Hilfiger Stream Rubber Chelsea Welly
    Tommy Hilfiger
    $110.04
    sizes
    available sizes: US9, US13
  15. Stream Tommy Hilfiger Black Rubber Chelsea Wellies
    Stream Tommy Hilfiger Black Rubber Chelsea Wellies
    Tommy Hilfiger
    $110.04
    sizes
    available sizes: US12
  16. Oliver Sweeney Mens Rocca Chelsea Boot Brogues
    Oliver Sweeney Mens Rocca Chelsea Boot Brogues
    Oliver Sweeney
    $425.68
    sizes
    available sizes: US9
  17. Light Brown Suede Chelsea Boot Brogues Oliver Sweeney
    Light Brown Suede Chelsea Boot Brogues Oliver Sweeney
    Oliver Sweeney
    $196.43
    sizes
    available sizes: US9, US11, US12
  18. Burnished Chelsea Boots Allegro Tan by Oliver Sweeney
    Burnished Chelsea Boots Allegro Tan by Oliver Sweeney
    Oliver Sweeney
    $242.28
    sizes
    available sizes: US8, US9, US10, US12
  19. Chocolate Brown Oliver Sweeney Chelsea Boot Brogues
    Chocolate Brown Oliver Sweeney Chelsea Boot Brogues
    Oliver Sweeney
    $196.43
    sizes
    available sizes: US9
  20. New Burnt Siena Brown Suede Chelsea Boots
    New Burnt Siena Brown Suede Chelsea Boots
    Kebo
    Special Price $111.28 Regular Price $130.93
    sizes
    available sizes: US7, US8, US10, US12, US13
  21. New Waxy Tobacco Suede Mens Slip On Boots
    New Waxy Tobacco Suede Mens Slip On Boots
    Kebo
    Special Price $111.28 Regular Price $130.93
    sizes
    available sizes: US7, US11, US14
  22. New Navy Blue Suede Plain Chelsea Boots for Men
    New Navy Blue Suede Plain Chelsea Boots for Men
    Kebo
    Special Price $111.28 Regular Price $130.93
    sizes
    available sizes: US8
  23. Chelsea Boots in Amazonas Tan by Anatomic & Co Shoes
    Chelsea Boots in Amazonas Tan by Anatomic & Co Shoes
    Anatomic
    $157.13
    sizes
    available sizes: US7, US9, US11, US12
  24. Chelsea Boots in Amazonas Black by Anatomic & Co
    Chelsea Boots in Amazonas Black by Anatomic & Co
    Anatomic
    $157.13
    sizes
    available sizes: US7, US8, US11, US12
  25. Cognac Wingtip Brogue Chelsea Boots by Anatomic Co
    Cognac Wingtip Brogue Chelsea Boots by Anatomic Co
    Anatomic
    $163.68
    sizes
    available sizes: US11, US12
  26. Black Brogue Chelsea Boots by Anatomic & Co Shoes
    Black Brogue Chelsea Boots by Anatomic & Co Shoes
    Anatomic
    Special Price $111.35 Regular Price $170.23
    sizes
    available sizes: US8, US10, US11, US12, US13
  27. Antiqued Wingcap Brogue Chelsea Boot Anatomic & Co
    Antiqued Wingcap Brogue Chelsea Boot Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US11
  28. Formal Cognac Mens Chelsea Boots Anatomic & Co
    Formal Cognac Mens Chelsea Boots Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US8, US9, US10, US11, US12, US13, US14
  29. Waxy Brown Plain Chelsea Boots by Anatomic & Co
    Waxy Brown Plain Chelsea Boots by Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US7, US8, US10, US11, US12
  30. Matt Black Mustang Chelsea Boots Anatomic & Co
    Matt Black Mustang Chelsea Boots Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US13
  31. Anatomic Shoes Brown Waxy Chelsea Boots
    Anatomic Shoes Brown Waxy Chelsea Boots
    Anatomic
    $163.68
    sizes
    available sizes: US12, US13
  32. Formal Black Mens Chelsea Boots Anatomic & Co
    Formal Black Mens Chelsea Boots Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US7, US8, US10, US11, US12, US13
  33. Thomas Partridge Brown Mens Cranwell Chelsea Boots
    Thomas Partridge Brown Mens Cranwell Chelsea Boots
    Thomas Partridge
    $162.44
    sizes
    available sizes: US11
  34. Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge
    $162.44
    sizes
    available sizes: US8, US9, US12
  35. Square Toe Steptronic Aston Chelsea Boots in Tan
    Square Toe Steptronic Aston Chelsea Boots in Tan
    Steptronic Shoes
    $157.13
    sizes
    available sizes: US14
  36. Steptronic Dark Conker Brown Mens Dealer Boots with Rubber Sole
    Steptronic Dark Conker Brown Mens Dealer Boots with Rubber Sole
    Steptronic Shoes
    $157.13
    sizes
    available sizes: US7
  37. Mephisto Colby Black Mens Chelsea Boots
    Mephisto Colby Black Mens Chelsea Boots
    Mephisto
    $229.18
    sizes
    available sizes: US8
  38. Tan Leather Bison Chelsea Boots by Exceed
    Tan Leather Bison Chelsea Boots by Exceed
    Exceed Shoes
    Special Price $144.03 Regular Price $189.95
    sizes
    available sizes: US7, US8, US10, US11
  39. Exceed Grey Leather Mens Chelsea Boots
    Exceed Grey Leather Mens Chelsea Boots
    Exceed Shoes
    Special Price $144.03 Regular Price $189.95
    sizes
    available sizes: US7, US8, US9, US10, US12, US14
  40. Exceed Brown Mens Chelsea Boots UK
    Exceed Brown Mens Chelsea Boots UK
    Exceed Shoes
    $189.95
    sizes
    available sizes: US8, US9, US13, US14
  41. Black Polished Mens Exceed Chelsea Boots
    Black Polished Mens Exceed Chelsea Boots
    Exceed Shoes
    $189.95
    sizes
    available sizes: US7, US8, US14
  42. Exceed Black Brogue Mens Chelsea Boots
    Exceed Black Brogue Mens Chelsea Boots
    Exceed Shoes
    Special Price $144.03 Regular Price $189.95
    sizes
    available sizes: US7, US8, US13, US14

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Chelsea Boots

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Chelsea Boots
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