Designer Chelsea Boots For Men

Arthur Knight Shoes are proud to offer the largest selection of elasticated slip-on designer Chelsea Boots for men with over 100 styles to choose from by famous designer brands. Originating in the 1800s as a type of leather riding boot known as jodhpur boots, the classic 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.

Black Chelsea boots 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 leather 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, Chelsea’s 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 slip on boots offered by Arthur Knight have robust, hard wearing soles and comfortable interior lining, as well as supportive foot beds, ensuring that your foot can breathe but remains snug and secure while you’re out walking. When cared for properly, a well-made Chelsea will serve you with comfortable wear for many years.

If you are looking for a classic, round toe tan Chelsea boot for men, we might direct you to the incredible range offered by John White. For a more flamboyant look, you could check out the brown leather boots by Jeffery West. Designer Chelsea boots for men 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. Calvin Klein Premium Tobacco Nubuck Leather Chelsea Boots
    Calvin Klein Premium Tobacco Nubuck Leather Chelsea Boots
    Calvin Klein
    $167.96
    sizes
    available sizes: US7, US8, US9, US10, US11, US12
  2. Calvin Klein Premium Olive Grey Mens Chelsea Boots
    Calvin Klein Premium Olive Grey Mens Chelsea Boots
    Calvin Klein
    $167.96
    sizes
    available sizes: US7, US8, US9, US10, US11, US12
  3. Barbour Sand Suede Sedgefield Demi Boots for Men
    Barbour Sand Suede Sedgefield Demi Boots for Men
    Barbour Shoes
    $141.92
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  4. Blundstone Black 515 Chelsea Boots with Blue Eastic
    Blundstone Black 515 Chelsea Boots with Blue Eastic
    Blundstone Boots
    $174.47
    sizes
    available sizes: US8, US9, US10, US11, US12
  5. Steptronic Fulham Slip On Chelsea Boots in Brown Leather
    Steptronic Fulham Slip On Chelsea Boots in Brown Leather
    Steptronic Shoes
    $154.94
    sizes
    available sizes: US9, US10, US11, US12
  6. Barbour Designer Light Brown Suede Bedlington Chelsea Boots
    Barbour Designer Light Brown Suede Bedlington Chelsea Boots
    Barbour Shoes
    $167.96
    sizes
    available sizes: US7, US8, US9
  7. Steptronic Formal Black Mens Wingtip Chelsea Boots
    Steptronic Formal Black Mens Wingtip Chelsea Boots
    Steptronic Shoes
    $167.96
    sizes
    available sizes: US8, US10, US11, US12
  8. Barbour International Designer Black Fargo Chelsea Boots
    Barbour International Designer Black Fargo Chelsea Boots
    Barbour Shoes
    Special Price $141.92 Regular Price $187.49
    sizes
    available sizes: US8, US9, US10, US11, US12
  9. Steptronic Square Toe Designer Black Mens Chelsea Boots
    Steptronic Square Toe Designer Black Mens Chelsea Boots
    Steptronic Shoes
    Special Price $128.90 Regular Price $167.96
    sizes
    available sizes: US7, US9, US10, US11, US12, US13
  10. Jeffery West Black Polished Cuban Chelsea Boot with Red Sole
    Jeffery West Black Polished Cuban Chelsea Boot with Red Sole
    Jeffery West Shoes
    $318.99
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  11. John White Premium Snuff Suede Mens Chelsea Boots
    John White Premium Snuff Suede Mens Chelsea Boots
    John White
    $240.87
    sizes
    available sizes: US9, US11, US12
  12. Anatomic Comfort Slip On Brogue Ankle Boot in Brown Leather
    Anatomic Comfort Slip On Brogue Ankle Boot in Brown Leather
    Anatomic
    $162.68
    sizes
    available sizes: US8, US10, US12, US13
  13. Barbour Matt Black Waxy Chelsea Boots with Rubber Sole
    Barbour Matt Black Waxy Chelsea Boots with Rubber Sole
    Barbour Shoes
    $154.94
    sizes
    available sizes: US8, US9, US11, US12
  14. Designer Bass Waxy Brown Suede Wedge Sole Chelsea Boots
    Designer Bass Waxy Brown Suede Wedge Sole Chelsea Boots
    Bass Weejuns
    $208.32
    sizes
    available sizes: US12
  15. Burgundy & Waxy Brown Chelsea Boot Brogues by Anatomic
    Burgundy & Waxy Brown Chelsea Boot Brogues by Anatomic
    Anatomic
    $169.19
    sizes
    available sizes: US9, US10, US11, US12
  16. English Jeffery West Chelsea Brogues in Black Polished
    English Jeffery West Chelsea Brogues in Black Polished
    Jeffery West Shoes
    $423.15
    sizes
    available sizes: US8
  17. Fire Red Jeffery West Chelsea Brogues in Black
    Fire Red Jeffery West Chelsea Brogues in Black
    Jeffery West Shoes
    $312.48
    sizes
    available sizes: US9, US10, US11, US12, US13
  18. Barbour Farsley Waxy Tan Chelsea Boots
    Barbour Farsley Waxy Tan Chelsea Boots
    Barbour Shoes
    $154.94
    sizes
    available sizes: US8, US9, US11, US12
  19. Burnished Chelsea Boots Allegro Tan by Oliver Sweeney
    Burnished Chelsea Boots Allegro Tan by Oliver Sweeney
    Oliver Sweeney
    $240.80
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  20. Oliver Sweeney Black & Purple Designer Chelsea Boots
    Oliver Sweeney Black & Purple Designer Chelsea Boots
    Oliver Sweeney
    $195.23
    sizes
    available sizes: US7, US8
  21. Chelsea Boots in Amazonas Black by Anatomic & Co
    Chelsea Boots in Amazonas Black by Anatomic & Co
    Anatomic
    $156.17
    sizes
    available sizes: US7
  22. Black Brogue Chelsea Boots by Anatomic & Co Shoes
    Black Brogue Chelsea Boots by Anatomic & Co Shoes
    Anatomic
    Special Price $110.67 Regular Price $169.19
    sizes
    available sizes: US8, US12, US13
  23. Formal Cognac Mens Chelsea Boots Anatomic & Co
    Formal Cognac Mens Chelsea Boots Anatomic & Co
    Anatomic
    $162.68
    sizes
    available sizes: US8
  24. Waxy Brown Plain Chelsea Boots by Anatomic & Co
    Waxy Brown Plain Chelsea Boots by Anatomic & Co
    Anatomic
    $162.68
    sizes
    available sizes: US7, US11
  25. Anatomic Shoes Brown Waxy Chelsea Boots
    Anatomic Shoes Brown Waxy Chelsea Boots
    Anatomic
    $162.68
    sizes
    available sizes: US8, US9
  26. Formal Black Mens Chelsea Boots Anatomic & Co
    Formal Black Mens Chelsea Boots Anatomic & Co
    Anatomic
    $162.68
    sizes
    available sizes: US7, US8, US9, US12, US13
  27. Thomas Partridge Brown Mens Cranwell Chelsea Boots
    Thomas Partridge Brown Mens Cranwell Chelsea Boots
    Thomas Partridge
    $161.45
    sizes
    available sizes: US8
  28. Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge
    $161.45
    sizes
    available sizes: US8, US10, US12
  29. Tan Leather Bison Chelsea Boots by Exceed
    Tan Leather Bison Chelsea Boots by Exceed
    Exceed Shoes
    $188.79
    sizes
    available sizes: US7, US8
  30. Exceed Grey Leather Mens Chelsea Boots
    Exceed Grey Leather Mens Chelsea Boots
    Exceed Shoes
    Special Price $143.15 Regular Price $188.79
    sizes
    available sizes: US7, US8, US9, US10, US11, US12, US13, US14
  31. Exceed Brown Mens Chelsea Boots UK
    Exceed Brown Mens Chelsea Boots UK
    Exceed Shoes
    Special Price $143.15 Regular Price $188.79
    sizes
    available sizes: US7, US8, US9, US10, US11, US12, US13
  32. Black Polished Mens Exceed Chelsea Boots
    Black Polished Mens Exceed Chelsea Boots
    Exceed Shoes
    Special Price $143.15 Regular Price $188.79
    sizes
    available sizes: US7, US9, US10, US11, US12, US13
  33. Exceed Black Brogue Mens Chelsea Boots
    Exceed Black Brogue Mens Chelsea Boots
    Exceed Shoes
    Special Price $143.15 Regular Price $188.79
    sizes
    available sizes: US7, US8, US9, US10, US11, US12, US13, US14
  34. Tan Leather Mens Chelsea Boots by Exceed
    Tan Leather Mens Chelsea Boots by Exceed
    Exceed Shoes
    Special Price $143.15 Regular Price $188.79
    sizes
    available sizes: US7, US8, US9, US10, US11, US12, US13
  35. Navy Blue Chelsea Boot Brogues by Exceed Shoes
    Navy Blue Chelsea Boot Brogues by Exceed Shoes
    Exceed Shoes
    Special Price $143.15 Regular Price $188.79
    sizes
    available sizes: US7, US8, US9, US10, US11, US13
  36. Carlos Santos Burnished Tan Chelsea Boots
    Carlos Santos Burnished Tan Chelsea Boots
    Carlos Santos Shoes
    Special Price $312.48 Regular Price $468.72
    sizes
    available sizes: US7
  37. Conquer by Carlos Santos Boots in Black Calf Suede
    Conquer by Carlos Santos Boots in Black Calf Suede
    Carlos Santos Shoes
    Special Price $312.48 Regular Price $468.72
    sizes
    available sizes: US8½, US10, US11, US12
  38. Conquer Carlos Santos Mens Boot in Brown Leather
    Conquer Carlos Santos Mens Boot in Brown Leather
    Carlos Santos Shoes
    $468.72
    sizes
    available sizes: US7, US10
  39. Carlos Santos Conquer Luxury Blue Chelsea Boots
    Carlos Santos Conquer Luxury Blue Chelsea Boots
    Carlos Santos Shoes
    $468.72
    sizes
    available sizes: US9
  40. Conquer Two Tone Rustic Wine Carlos Santos Shoes
    Conquer Two Tone Rustic Wine Carlos Santos Shoes
    Carlos Santos Shoes
    Special Price $312.48 Regular Price $468.72
    sizes
    available sizes: US9½
  41. John White Shoes Chelsea R Boots in Brown Suede Leather Rubber Sole
    John White Shoes Chelsea R Boots in Brown Suede Leather Rubber Sole
    John White
    $227.85
    sizes
    available sizes: US8
  42. Black John White Chelsea Boot with Leather Sole
    Black John White Chelsea Boot with Leather Sole
    John White
    Special Price $188.79 Regular Price $240.87
    sizes
    available sizes: US8

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