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. Black Polished Sherman Premium Formal Chelsea Boots
    Black Polished Sherman Premium Formal Chelsea Boots
    Arthur Knight Shoes
    $148.80
    sizes
    available sizes: US9, US10, US11, US12
  2. Jeffery West Goodyear Welted Diamond Brown Chelsea Boots
    Jeffery West Goodyear Welted Diamond Brown Chelsea Boots
    Jeffery West Shoes
    $462.00
    sizes
    available sizes: US9, US10, US11, US12
  3. Bugatti Mens Chelsea Zip Buckle Boots in Brown
    Bugatti Mens Chelsea Zip Buckle Boots in Brown
    Bugatti Mens Shoes
    $143.94
    sizes
    available sizes: US8, US9, US10, US11, US12, US13
  4. Jeffery West Black Polished Red Elastic Wingtip Chelsea Brogue
    Jeffery West Black Polished Red Elastic Wingtip Chelsea Brogue
    Jeffery West Shoes
    $318.00
    sizes
    available sizes: US9, US10, US12
  5. Bugatti Antique Brown Mens Designer Chelsea Boots
    Bugatti Antique Brown Mens Designer Chelsea Boots
    Bugatti Mens Shoes
    $143.94
    sizes
    available sizes: US11, US12
  6. Tommy Hilfiger Navy Blue Suede Designer Chelsea Boots
    Tommy Hilfiger Navy Blue Suede Designer Chelsea Boots
    Tommy Hilfiger
    Special Price $118.80 Regular Price $160.80
    sizes
    available sizes: US10, US11
  7. Tommy Hilfiger Brown Suede Designer Chelsea Boots for Men
    Tommy Hilfiger Brown Suede Designer Chelsea Boots for Men
    Tommy Hilfiger
    $160.80
    sizes
    available sizes: US7½, US10, US11
  8. Arthur Knight Mayfair Tan Leather Designer Chelsea Boot
    Arthur Knight Mayfair Tan Leather Designer Chelsea Boot
    Arthur Knight Shoes
    Special Price $142.80 Regular Price $178.80
    sizes
    available sizes: US10, US11, US12
  9. Arthur Knight Mayfair Black Designer Chelsea Boots
    Arthur Knight Mayfair Black Designer Chelsea Boots
    Arthur Knight Shoes
    Special Price $142.80 Regular Price $178.80
    sizes
    available sizes: US8, US11, US12
  10. John White Light Brown Leather Mens Chelsea Boots
    John White Light Brown Leather Mens Chelsea Boots
    John White
    $222.00
    sizes
    available sizes: US10, US11
  11. Jeffery West Italian Fire Red Silver Black Chelsea Boot
    Jeffery West Italian Fire Red Silver Black Chelsea Boot
    Jeffery West Shoes
    $474.00
    sizes
    available sizes: US9
  12. Calvin Klein Premium Tobacco Nubuck Leather Chelsea Boots
    Calvin Klein Premium Tobacco Nubuck Leather Chelsea Boots
    Calvin Klein
    Special Price $106.80 Regular Price $154.80
    sizes
    available sizes: US8, US9, US10, US11½
  13. Calvin Klein Premium Olive Grey Mens Chelsea Boots
    Calvin Klein Premium Olive Grey Mens Chelsea Boots
    Calvin Klein
    Special Price $82.80 Regular Price $154.80
    sizes
    available sizes: US8, US9, US10, US11, US11½, US12
  14. Barbour Sand Suede Sedgefield Demi Boots for Men
    Barbour Sand Suede Sedgefield Demi Boots for Men
    Barbour Shoes
    $130.80
    sizes
    available sizes: US8, US9
  15. Blundstone Black 515 Chelsea Boots with Blue Eastic
    Blundstone Black 515 Chelsea Boots with Blue Eastic
    Blundstone Boots
    $166.80
    sizes
    available sizes: US11, US12
  16. Barbour Designer Light Brown Suede Bedlington Chelsea Boots
    Barbour Designer Light Brown Suede Bedlington Chelsea Boots
    Barbour Shoes
    $154.80
    sizes
    available sizes: US7, US8
  17. Jeffery West Black Polished Cuban Chelsea Boot with Red Sole
    Jeffery West Black Polished Cuban Chelsea Boot with Red Sole
    Jeffery West Shoes
    $294.00
    sizes
    available sizes: US9
  18. Barbour Matt Black Waxy Chelsea Boots with Rubber Sole
    Barbour Matt Black Waxy Chelsea Boots with Rubber Sole
    Barbour Shoes
    Special Price $118.80 Regular Price $142.80
    sizes
    available sizes: US8, US9, US10, US11, US12
  19. Designer Bass Waxy Brown Suede Wedge Sole Chelsea Boots
    Designer Bass Waxy Brown Suede Wedge Sole Chelsea Boots
    Bass Weejuns
    $270.00
    sizes
    available sizes: US12
  20. Burgundy & Waxy Brown Chelsea Boot Brogues by Anatomic
    Burgundy & Waxy Brown Chelsea Boot Brogues by Anatomic
    Anatomic
    $155.94
    sizes
    available sizes: US10, US11
  21. Fire Red Jeffery West Chelsea Brogues in Black
    Fire Red Jeffery West Chelsea Brogues in Black
    Jeffery West Shoes
    $288.00
    sizes
    available sizes: US10
  22. Burnished Chelsea Boots Allegro Tan by Oliver Sweeney
    Burnished Chelsea Boots Allegro Tan by Oliver Sweeney
    Oliver Sweeney
    Special Price $179.94 Regular Price $239.94
    sizes
    available sizes: US8, US10, US11, US12
  23. Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge London Tan Cranwell Chelsea Boots
    Thomas Partridge
    $148.80
    sizes
    available sizes: US8
  24. Exceed Brown Mens Chelsea Boots UK
    Exceed Brown Mens Chelsea Boots UK
    Exceed Shoes
    Special Price $131.94 Regular Price $174.00
    sizes
    available sizes: US7, US8, US13
  25. Exceed Black Brogue Mens Chelsea Boots
    Exceed Black Brogue Mens Chelsea Boots
    Exceed Shoes
    Special Price $131.94 Regular Price $174.00
    sizes
    available sizes: US7, US13, US14
  26. Tan Leather Mens Chelsea Boots by Exceed
    Tan Leather Mens Chelsea Boots by Exceed
    Exceed Shoes
    Special Price $131.94 Regular Price $174.00
    sizes
    available sizes: US7, US8, US13
  27. Carlos Santos Burnished Tan Chelsea Boots
    Carlos Santos Burnished Tan Chelsea Boots
    Carlos Santos Shoes
    Special Price $288.00 Regular Price $432.00
    sizes
    available sizes: US8½
  28. Conquer Carlos Santos Mens Boot in Brown Leather
    Conquer Carlos Santos Mens Boot in Brown Leather
    Carlos Santos Shoes
    Special Price $264.00 Regular Price $432.00
    sizes
    available sizes: US7
  29. Brown Suede Goodyear Welted Wholecut Chelsea Boot
    Brown Suede Goodyear Welted Wholecut Chelsea Boot
    Arthur Knight Shoes
    $294.00
    sizes
    available sizes: US9
  30. Deer Skin Mens Chelsea Boots in Antique Tan
    Deer Skin Mens Chelsea Boots in Antique Tan
    Arthur Knight Shoes
    $234.00
    sizes
    available sizes: US8, US11
  31. Purple Aubergine Chelsea Boots for Men
    Purple Aubergine Chelsea Boots for Men
    Arthur Knight Shoes
    $288.00
    sizes
    available sizes: US10
  32. Trickers Beechnut Lambourn Dealer Boot
    Trickers Beechnut Lambourn Dealer Boot
    Trickers
    Special Price $342.00 Regular Price $702.00
    sizes
    available sizes: US9
  33. Steptronic Austin Formal Black Leather Chelsea Boots
    Steptronic Austin Formal Black Leather Chelsea Boots
    Steptronic Shoes
    $155.94
    sizes
    available sizes: US8
  34. Barbour Light Tan Farsley Mens Slip On Chelsea Boot
    Barbour Light Tan Farsley Mens Slip On Chelsea Boot
    Barbour Shoes
    $142.80
    sizes
    available sizes: US10, US11, US12
  35. Jeffery West Honey Leather Diamond Chelsea Boot With Red Sole
    Jeffery West Honey Leather Diamond Chelsea Boot With Red Sole
    Jeffery West Shoes
    Special Price $342.00 Regular Price $438.00
    sizes
    available sizes: US9, US10, US11, US12
  36. Jeffery West Black Leather Designer Chelsea Boot Brogues
    Jeffery West Black Leather Designer Chelsea Boot Brogues
    Jeffery West Shoes
    $294.00
    sizes
    available sizes: US9, US10, US11
  37. Steptronic Buckingham 2 Country Brogue Boot in Black
    Steptronic Buckingham 2 Country Brogue Boot in Black
    Steptronic Shoes
    $167.94
    sizes
    available sizes: US8
  38. Brown Polished Sherman Premium Formal Chelsea Boots
    Brown Polished Sherman Premium Formal Chelsea Boots
    Arthur Knight Shoes
    $148.80
    sizes
    available sizes: US9, US10, US11, US12
  39. Jeffery West Black Polished Diamond Chelsea Boot with Red Sole
    Jeffery West Black Polished Diamond Chelsea Boot with Red Sole
    Jeffery West Shoes
    Special Price $342.00 Regular Price $438.00
    sizes
    available sizes: US9, US9½, US10, US10½, US11, US12
  40. Jeffery West Premium Brown Chelsea Boot Brogues
    Jeffery West Premium Brown Chelsea Boot Brogues
    Jeffery West Shoes
    $390.00
    sizes
    available sizes: US8, US9, US10, US11
  41. Calvin Klein Premium Brown Suede Mens Chelsea Boots
    Calvin Klein Premium Brown Suede Mens Chelsea Boots
    Calvin Klein
    $154.80
    sizes
    available sizes: US7½, US8, US9
  42. Jeffery West Premium Antique Tan Diamond Chelsea Boots
    Jeffery West Premium Antique Tan Diamond Chelsea Boots
    Jeffery West Shoes
    Special Price $342.00 Regular Price $462.00
    sizes
    available sizes: US9, US10, US11, US12

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