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. John White Premium Snuff Suede Mens Chelsea Boots
    John White Premium Snuff Suede Mens Chelsea Boots
    John White
    $242.35
    sizes
    available sizes: US8, US9, US10, US11, US12
  2. Anatomic Comfort Slip On Brogue Ankle Boot in Brown Leather
    Anatomic Comfort Slip On Brogue Ankle Boot in Brown Leather
    Anatomic
    $163.68
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  3. Barbour Matt Black Waxy Chelsea Boots with Rubber Sole
    Barbour Matt Black Waxy Chelsea Boots with Rubber Sole
    Barbour Shoes
    $155.89
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  4. Designer Bass Waxy Brown Suede Wedge Sole Chelsea Boots
    Designer Bass Waxy Brown Suede Wedge Sole Chelsea Boots
    Bass Weejuns
    $209.60
    sizes
    available sizes: US10, US12
  5. Exclusive Jeffery West Black Polished Skull Chelsea Boots
    Exclusive Jeffery West Black Polished Skull Chelsea Boots
    Jeffery West Shoes
    $281.65
    sizes
    available sizes: US9
  6. 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
  7. Black & Grey Mens 1452 Blundstone Chelsea Boots
    Black & Grey Mens 1452 Blundstone Chelsea Boots
    Blundstone Boots
    $149.34
    sizes
    available sizes: US11
  8. 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
  9. Jeffery West Dark Burgundy Red Elastic Chelsea Boots
    Jeffery West Dark Burgundy Red Elastic Chelsea Boots
    Jeffery West Shoes
    $432.30
    sizes
    available sizes: US12
  10. Black Suede & Burgundy Oliver Sweeney Chelsea Boots
    Black Suede & Burgundy Oliver Sweeney Chelsea Boots
    Oliver Sweeney
    $196.43
    sizes
    available sizes: US8
  11. Double Wingtip Brown Jeffery West Chelsea Brogues
    Double Wingtip Brown Jeffery West Chelsea Brogues
    Jeffery West Shoes
    $288.20
    sizes
    available sizes: US8
  12. Navy Blue John White Slip on Chelsea Boots
    Navy Blue John White Slip on Chelsea Boots
    John White
    $176.85
    sizes
    available sizes: US8, US12
  13. 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: US9, US12
  14. 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, US12
  15. Barbour Farsley Waxy Tan Chelsea Boots
    Barbour Farsley Waxy Tan Chelsea Boots
    Barbour Shoes
    $155.89
    sizes
    available sizes: US8, US9
  16. Light Brown Suede Chelsea Boot Brogues Oliver Sweeney
    Light Brown Suede Chelsea Boot Brogues Oliver Sweeney
    Oliver Sweeney
    $196.43
    sizes
    available sizes: US9
  17. Oliver Sweeney Black & Purple Designer Chelsea Boots
    Oliver Sweeney Black & Purple Designer Chelsea Boots
    Oliver Sweeney
    $196.43
    sizes
    available sizes: US7
  18. New Burnt Siena Brown Suede Chelsea Boots
    New Burnt Siena Brown Suede Chelsea Boots
    Kebo
    Special Price $110.04 Regular Price $130.93
    sizes
    available sizes: US7, US8, US10, US12
  19. Chelsea Boots in Amazonas Tan by Anatomic & Co Shoes
    Chelsea Boots in Amazonas Tan by Anatomic & Co Shoes
    Anatomic
    $157.13
    sizes
    available sizes: US9, US10
  20. Chelsea Boots in Amazonas Black by Anatomic & Co
    Chelsea Boots in Amazonas Black by Anatomic & Co
    Anatomic
    $157.13
    sizes
    available sizes: US7, US9, US10, US11, US12
  21. 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, US12, US13
  22. 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
  23. Waxy Brown Plain Chelsea Boots by Anatomic & Co
    Waxy Brown Plain Chelsea Boots by Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US7, US10, US11, US12
  24. Matt Black Mustang Chelsea Boots Anatomic & Co
    Matt Black Mustang Chelsea Boots Anatomic & Co
    Anatomic
    $163.68
    sizes
    available sizes: US13
  25. Anatomic Shoes Brown Waxy Chelsea Boots
    Anatomic Shoes Brown Waxy Chelsea Boots
    Anatomic
    $163.68
    sizes
    available sizes: US8, US10, US11, US12
  26. 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
  27. Thomas Partridge Brown Mens Cranwell Chelsea Boots
    Thomas Partridge Brown Mens Cranwell Chelsea Boots
    Thomas Partridge
    $162.44
    sizes
    available sizes: US8, US10, US12
  28. Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge
    $162.44
    sizes
    available sizes: US8, US9, US10, US11, US12
  29. Square Toe Steptronic Aston Chelsea Boots in Tan
    Square Toe Steptronic Aston Chelsea Boots in Tan
    Steptronic Shoes
    $157.13
    sizes
    available sizes: US14
  30. 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
  31. Tan Leather Bison Chelsea Boots by Exceed
    Tan Leather Bison Chelsea Boots by Exceed
    Exceed Shoes
    $189.95
    sizes
    available sizes: US7, US8
  32. 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, US11, US12, US13, US14
  33. Exceed Brown Mens Chelsea Boots UK
    Exceed Brown Mens Chelsea Boots UK
    Exceed Shoes
    $189.95
    sizes
    available sizes: US8
  34. Black Polished Mens Exceed Chelsea Boots
    Black Polished Mens Exceed Chelsea Boots
    Exceed Shoes
    Special Price $144.03 Regular Price $189.95
    sizes
    available sizes: US7, US9, US10, US11, US12, US13, US14
  35. 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, US9, US10, US11, US13, US14
  36. Tan Leather Mens Chelsea Boots by Exceed
    Tan Leather Mens Chelsea Boots by Exceed
    Exceed Shoes
    Special Price $144.03 Regular Price $189.95
    sizes
    available sizes: US7, US8, US9, US11, US12, US13, US14
  37. Navy Blue Chelsea Boot Brogues by Exceed Shoes
    Navy Blue Chelsea Boot Brogues by Exceed Shoes
    Exceed Shoes
    Special Price $144.03 Regular Price $189.95
    sizes
    available sizes: US9, US10, US11, US12, US14
  38. Carlos Santos Burnished Tan Chelsea Boots
    Carlos Santos Burnished Tan Chelsea Boots
    Carlos Santos Shoes
    Special Price $314.40 Regular Price $471.60
    sizes
    available sizes: US7, US8½
  39. Conquer by Carlos Santos Boots in Black Calf Suede
    Conquer by Carlos Santos Boots in Black Calf Suede
    Carlos Santos Shoes
    $471.60
    sizes
    available sizes: US8½
  40. Conquer Carlos Santos Mens Boot in Brown Leather
    Conquer Carlos Santos Mens Boot in Brown Leather
    Carlos Santos Shoes
    Special Price $314.40 Regular Price $471.60
    sizes
    available sizes: US7, US10
  41. Carlos Santos Conquer Luxury Blue Chelsea Boots
    Carlos Santos Conquer Luxury Blue Chelsea Boots
    Carlos Santos Shoes
    $471.60
    sizes
    available sizes: US9, US9½
  42. Conquer Two Tone Rustic Wine Carlos Santos Shoes
    Conquer Two Tone Rustic Wine Carlos Santos Shoes
    Carlos Santos Shoes
    Special Price $314.40 Regular Price $471.60
    sizes
    available sizes: US8½, US9½

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Chelsea Boots

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Chelsea Boots
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