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Men's Chelsea Boots

386 Results
386 results
  1. The Black Dr. Martens 2976 Chelsea Boots Have A Leather Upper, The Iconic Yellow Stitching, And Airwair Heel Loop, Which Gives Them That Doc Martens Edge. Featuring The Famous Air-cushioned Airwair Sole With The Traditional Rugged Tread And Goodyear Welt For Enhanced Durability. These Shoes Stand Out From The Crowd In The Legendary Docs Look.

    Dr. Martens

    Dr Martens 2976 Ambassador Boots

    £170.00£134.0021% Off
  2. Selling Fast! Sold 43 times
    These Dr. Martens Chelsea boots are crafted from a heavyweight and oily leather that’s been tumbled. With elasticated side panels and branded heel tabs to ensure the perfect fit and an easy on/off. The iconic chunky PVC sole is Goodyear welted yellow stitching with bouncing Air Wair technology.

    Dr. Martens

    Dr. Martens 2976 Ambassador Leather Black Boots

    £170.00£134.0021% Off
  3. Selling Fast! Sold 10 times
    Looking for a new style this season? We love the Crew, a must-have boot featuring a chunky statement sole and timeless round toe. Designed to keep you comfy and stylish all day long, they feature a pull tab for ease when putting on.

    Dune London

    Dune Mens Crew - Suede Chunky Chelsea Boots

    £120.00£35.0071% Off
    +3 colours
  4. Selling Fast! Sold 5 times
    STB STB ELLIS Unisex Leather Air Cushioned Dealer Boots Waxy Brown Upper Material: Leather Lining Material: Textile Sole Material: Synthetic Closure/Fastening: Slip-On Features: Comfort,Breathable Toe Shape: Round Shoe Width: Regular Item Weight: 1.66 KG Heel Height: Flat (Under 2.5cm) Shoe Shaft Height: Ankle Boot Style: Occupational/Non-Safety Boots Safety Features: Water Resistant Product Code: ELLIS/BRN

    STB

    STB ELLIS Unisex Leather Air Cushioned Dealer Boots Waxy Brown

    £44.99£35.9920% Off
    +4 colours
  5. Mens brown Oliver Sweeney baltimore boots, manufactured with leather and a leather sole. Featuring: blake stitched leather sole, side gussets, oliver sweeney branding and leather lining.

    Oliver Sweeney

    Oliver Sweeney Baltimore Boots

    £279.00£160.0043% Off
  6. STB STB ELLIS Unisex Leather Air Cushioned Dealer Boots Polished Black Upper Material: Leather Lining Material: Textile Sole Material: Synthetic Closure/Fastening: Slip-On Features: Comfort,Breathable Toe Shape: Round Shoe Width: Regular Item Weight: 1.66 KG Heel Height: Flat (Under 2.5cm) Shoe Shaft Height: Ankle Boot Style: Occupational/Non-Safety Boots Safety Features: Water Resistant Product Code: ELLIS/PBLK

    STB

    STB ELLIS Unisex Leather Air Cushioned Dealer Boots Polished Black

    £44.99£33.7425% Off
    +4 colours
  7. The #587 is part of the Blundstone Classics collection a series of round-toe lined Chelsea boot styles. Comprised of high quality rustic black leather they'll compliment a variety of outfits. Strong grooved outsoles provide a solid grip in all weather and work together with XRD Technology and removable EVA footbeds to cushion and support your feet all-day long.

    Blundstone

    Blundstone Classics 587 Rustic Black Boots

    £185.00£149.849% Off
  8. Men's Tan Simon Carter Elgar 2 Lace-up Chelsea Boots With Smooth Suede Leather Upper, Fine Details, Designer Branded Textile Heel Tab And Exclusive Printed Lining And Sock. These Smart, Exclusive Simon Carter Men's Shoes Are Your Stylish Staple For Many Occasions.

    Simon Carter

    Simon Carter Elgar 2 Chelsea Boots

    £99.99£72.9927% Off
  9. Classic Chelsea, rugged upgrade. The Zinc Boot features rich pull-up leathers, an elasticated gusset, and a nylon pull-tab for easy wear. A cleated rubber sole adds grip, while the Ortholite insole keeps things comfy. Smart, sturdy, effortless.

    Base London

    Base London Zinc Leather Men's Tan Boots

    £85.00£69.9118% Off
  10. A Fine Example Of Fashion With A Conscience, These Vegan-friendly Chelsea Boots From Dr Martens In Classic Black Will Instantly Update Your Everyday Outfit. Contrary To Their Sturdy Appearance, The Pull On Elasticised Ankle And Cushioned Airwair Sole Make These Boots As Comfortable As They Are Stylish.

    Dr. Martens

    Dr Martens Vegan 2976 Boots

    £170.00£133.4921% Off
  11. The Pascal Chelsea Boot leather brings timeless style and winter-ready performance. Crafted with premium waterproof leather, a soft padded insole, and a durable TPR outsole, it's designed for comfort and quality all through the season.

    Hush Puppies

    Hush Puppies Pascal Leather Men's Tan Boots

    £115.00£82.3028% Off
  12. Gear up for adventure with our Colton boot. This design features our signature stacked coloured insert heel and a lace up fastening ending in hook fastenings. Crafted from leather the addition of the contrasting padded cuffs adds all-day comfort.

    Dune London

    Dune Mens Colton - Lace Up Hiker Boot

    £130.00£39.0070% Off
  13. Men's Tan Simon Carter Terrier Pull-on Chelsea Boots With Smooth Leather Upper, Double Elasticated Gussets And Delicate Stitch Detailing. These Premium Ankle Boots Have An Elongated Toe, Branded Heel Pull Tab And Leather Lining And Exclusive Simon Carter Queuing Dog Print, Finished With A Synthetic Sole.

    Simon Carter

    Simon Carter Terrier Chelsea Boots

    £110.00£80.0027% Off
  14. Men's Black Simon Carter Terrier Pull-on Chelsea Boots With Smooth Leather Upper, Double Elasticated Gussets And Delicate Stitch Detailing. These Premium Ankle Boots Have An Elongated Toe, Branded Heel Pull Tab And Leather Lining And Exclusive Simon Carter Queuing Dog Print, Finished With A Synthetic Sole.

    Simon Carter

    Simon Carter Terrier Chelsea Boots

    £110.00£80.0027% Off
  15. A classic Chelsea boot featuring elastic for easy on and off, a soft microfibre lining, and comfy foam footbed, the Russell is a great every day pick for comfort and style

    Hush Puppies

    Hush Puppies Russell Leather Men's Tan Boots

    £95.00£69.0927% Off
  16. Pax by KG Kurt Geiger is a brown chelsea boot with elasticated side panels.

    KG Kurt Geiger

    KG Kurt Geiger Leather Pax Boots

    £129.00£79.0039% Off
  17. The 585 is part of the Blundstone Classics collection a series of round-toe lined Chelsea boot styles. Comprised of high quality rustic brown leather they'll compliment a variety of outfits. Strong grooved outsoles provide a solid grip in all weather and work together with XRD™ Technology and removable EVA footbeds to cushion and support your feet all-day long.

    Blundstone

    Blundstone 585 Classic Unisex Boot

    £185.00£154.7916% Off
  18. Ben Sherman Lombard Leather Mens Desert Boots Black. Leather Upper. Fabric Lining. Synthetic Sole. Mens Gentlemens Ben Sherman Lombard Leather Chelsea Boots Slip On.

    Ben Sherman

    Ben Sherman lombard leather Mens Desert Boots black

    £89.99£47.9947% Off
  19. Mens Frank James Brogue Leather Upper Dealer Boots. These Brogue chealsea boots are a durable yet fashionable pair that are fit for all occasions - smart or casual. With a cushioned sole these boots are also a comfortable and hard wearing fit. Available in Black, Bordo Brown or Tan in UK 6-12

    Frank James

    Frank James Warkton Leather Bordo Mens Cushioned Brogue Chelsea Boots

    £74.99£44.9840% Off
  20. STB STB ELLIS Unisex Leather Air Cushioned Dealer Boots Waxy Black Upper Material: Leather Lining Material: Textile Sole Material: Synthetic Closure/Fastening: Slip-On Features: Comfort,Breathable Toe Shape: Round Shoe Width: Regular Item Weight: 1.66 KG Heel Height: Flat (Under 2.5cm) Shoe Shaft Height: Ankle Boot Style: Occupational/Non-Safety Boots Safety Features: Water Resistant Product Code: ELLIS/BLK

    STB

    STB ELLIS Unisex Leather Air Cushioned Dealer Boots Waxy Black

    £44.99£35.9920% Off
    +4 colours
  21. A classic Chelsea boot featuring elastic for easy on and off, a soft microfibre lining, and comfy foam footbed, the Russell is a great every day pick for comfort and style

    Hush Puppies

    Hush Puppies Russell Leather Men's Brown Boots

    £95.00£69.0927% Off
  22. Synonymous with Dune London, the Chelsea boot is a long-standing classic favoured for its transitional appeal. Signature style Mandatory perfectly blends a contemporary aesthetic with our iconic heritage. Crafted from the finest material and detailed with a quintessential elastic side gusset and grosgrain pull tab, this almond-toed silhouette has been set on a durable rubber outsole. Finished with tonal stitching, this timeless style will become a go-to dressing solution throughout the season.

    Dune London

    Dune Mens MANDATORY Chelsea Boots Mandatory

    £129.00£90.0030% Off
  23. Benchgrade handmade footware. The Benchgrade brand was established in 1920 in London and strive to provide quality and hardwearing footwear. Ideal for any formal or casual occasions, in tan brown or black with full leather lining and goodyear welted leather sole. This handmade harewood dealer also includes a leather heel with pvc insert for traction. Availble in size 7-12

    Frank James

    Frank James Stratford Leather Tan Mens Chelsea Boots

    £139.99£73.9847% Off
  24. Built to weather the elements, the Blundstone 584s are your best friends as temperatures begin to fall. With fully waterproof premium brown leather uppers, these boots will help keep your feet nice and dry. In addition, the genuine removable sheepskin fleece footbed is supremely comfortable and with Blundstone's Thinsulate lining throughout the boot, it will help to keep your feet toasty and dry. These added cold-weather features come with the unrivalled comfort, durability and style that you have come to expect from Blundstone boots, with durable TPU outsole for enhanced traction on slippery terrains, and the patented SPS Max Comfort system for reduced wearer fatigue and increased comfort. A staple for any cold-weather wardrobe, these insulated Blundstone 584 thermal leather boots are perfect for the outdoors, whether in the snow or the rain. Premium rustic brown waterproof leather uppers Waterproof brown elasticated sides and iconic pull tags for easy slip-on Latexed seams to ensure waterproofing Thermal Thinsulate® insulation for warmth Removable shearling sheepskin footbed for warmth and comfort Highly durable TPU outsole ensures excellent traction on all terrains and outstanding durability Blundstone SPS Max Comfort system for superb comfort Lightweight and comfortable

    Blundstone

    Blundstone #584 Rustic Brown Thermal Chelsea Boot

    £210.00£180.3014% Off
  25. The Tan Dr. Martens 2976 Chelsea Boots Have A Leather Upper, The Iconic Yellow Stitching, And Airwair Heel Loop, Which Gives Them That Doc Martens Edge. Featuring The Famous Air-cushioned Airwair Sole With The Traditional Rugged Tread And Goodyear Welt For Enhanced Durability. These Shoes Stand Out From The Crowd In The Legendary Docs Look.

    Dr. Martens

    Dr Martens 2976 Boots

    £170.00£133.4921% Off
  26. The 550 in walnut is the perfect versatile boots for any weather. Featuring a premium upper leather material and leather lining. These boots have a contoured EVA cushion insole which provide support for all day wear with a thick outsole.

    Blundstone

    Blundstone Classic Walnut Brown Boots

    £185.00£149.8417% Off
  27. Step Into Pure Luxury With The Lineus Chelsea Boot From Ted Baker. With A Geometric Elastic Panel On The Ankle, These Classic Chelsea Boots Add A Contemporary Twist To A Classic Style. High-quality Top-grain Leather And A Comfortable Fit Make Them Perfect For Any Occasion, Whether You're Dressing Up Or Down, Adding A Sophisticated Flair To Your Looks.

    Ted Baker

    Ted Baker Lineus Boots

    £149.99£99.9933% Off
  28. Mens Frank James Brogue Leather Upper Dealer Boots. These Brogue chealsea boots are a durable yet fashionable pair that are fit for all occasions - smart or casual. With a cushioned sole these boots are also a comfortable and hard wearing fit. Available in Black, Bordo Brown or Tan in UK 6-12

    Frank James

    Frank James Warkton Leather Tan Mens Cushioned Brogue Chelsea Boots

    £74.99£44.9840% Off
  29. Pax by KG Kurt Geiger is a black chelsea boot with elasticated side panels.

    KG Kurt Geiger

    KG Kurt Geiger Leather Pax Boots

    £129.00£79.0039% Off
  30. Expertly constructed from the finest leather, this timeless and traditional silhouette will provide a sartorial foundation to any wardrobe. Constructed with elastic side panels and featuring a rear pull tab Maccles fuses master craftsmanship with contemporary British styling.

    Dune London

    Dune Mens Maccles - Maccles - Smart Leather Chelsea Boots

    £130.00£65.0050% Off
  31. Synonymous with Dune London, the Chelsea boot is a long-standing classic favoured for its transitional appeal. Signature style Mandatory perfectly blends a contemporary aesthetic with our iconic heritage. Crafted from the finest material and detailed with a quintessential elastic side gusset and grosgrain pull tab, this almond-toed silhouette has been set on a durable rubber outsole. Finished with tonal stitching, this timeless style will become a go-to dressing solution throughout the season.

    Dune London

    Dune Mens MANDATORY Chelsea Boots Mandatory

    £129.00£90.0030% Off
  32. Synonymous with Dune London, the Chelsea boot is a long-standing classic favoured for its transitional appeal. Signature style Mandatory perfectly blends a contemporary aesthetic with our iconic heritage. Crafted from the finest material and detailed with a quintessential elastic side gusset and grosgrain pull tab, this almond-toed silhouette has been set on a durable rubber outsole. Finished with tonal stitching, this timeless style will become a go-to dressing solution throughout the season.

    Dune London

    Dune Mens MANDATORY Chelsea Boots Mandatory

    £129.00£90.0030% Off
  33. These Black Dr Martens 2976 Black Chelsea Boots For Men Are A Distinctive And Timeless Entrant To The Dr. Martens Collection. Featuring Goodyear Welt, Side Gussets, Heel Loop, Iconic Yellow Stitching And The Famous Airwair Cushioned Sole.

    Dr. Martens

    Dr Martens 2976 Boots

    £170.00£134.0021% Off
  34. Caspian is a versatile boot that will become a welcome addition to your wardrobe. Constructed from soft premium leather, this style features a classic round toe, elasticated inserts and a chunky cleated sole for extra comfort and durability.

    Dune London

    Dune Mens Caspian - Leather Chelsea Boots

    £140.00£95.0032% Off
  35. Inspired by the rolling hills of the Cotswolds and terrains that demand more from your footwear, the Bodicote is a mens rugged country waterproof Chelsea boot crafted with a premium Nubuck leather upper and chunky hardwearing sole. Men's rugged country waterproof Chelsea boot crafted with a premium Nubuck leather upper- Embossed Cotswold branding on side.

    Cotswold

    Cotswold Bodicote WATERPROOF Mens

    £87.99£63.9927% Off
  36. A classic wardrobe staple, Roamers present these Palermo men's chelsea boots, delivered in a premium leather upper in a crisp black colourway with a durable rubber outsole.- Leather upper - Padded footbed - Fuller fitting design - Heel tab - Twin gussets for slip on wear - Flexi TR Sole

    Roamers

    Roamers Palermo Boots Mens

    £57.99£40.0027% Off
  37. The #587 is part of the Blundstone Classics collection a series of round-toe lined Chelsea boot styles. Comprised of high quality rustic black leather they'll compliment a variety of outfits. Strong grooved outsoles provide a solid grip in all weather and work together with XRD Technology and removable EVA footbeds to cushion and support your feet all-day long.

    Blundstone

    Blundstone 587 Classic Unisex Boot

    £185.00£154.7916% Off
  38. Expertly constructed from the finest material, this timeless and traditional silhouette will provide a sartorial foundation to any wardrobe. Constructed with elastic side panels and a contrasting sole Characteristic fuses master craftsmanship with contemporary British styling. Fits bigger to size. We recommend ordering the next size down.

    Dune London

    Dune Mens Characteristic - Characteristic - Smart Chelsea Boots

    £130.00£102.1021% Off
  39. Mens Frank James Brogue Leather Upper Dealer Boots. These Brogue chealsea boots are a durable yet fashionable pair that are fit for all occasions - smart or casual. With a cushioned sole these boots are also a comfortable and hard wearing fit. Available in Black, Bordo Brown or Tan in UK 6-12

    Frank James

    Frank James Warkton Leather Oxblood Mens Cushioned Brogue Chelsea Boots

    £74.99£44.9840% Off
  40. Brand new from Thomas Crick (Formally Red Tape). These chelsea boots are a step above the rest with better quality leather, a comfortable fashion styled sole and wicking lining. Classic yet modern brogue styling and contrast sole make these boots the must have for this season.

    Red Tape

    Red Tape Beeston Leather Tan Mens Chelsea Boots

    £69.99£38.9744% Off
  41. Embrace The Elements This Season In The Yuma Chelsea Men’s Boots From Wrangler. The Black Leather Slip On Boot Is Finished With A Chunky Cleated Sole.

    Wrangler

    Wrangler Yuma Chelsea Boots

    £99.99£68.9831% Off
  42. Purapiel Warranty, 10 years warranty. Casual boots for men. Made with 100% natural leather, free of Chromium VI. Made with the highest quality materials. Manufactured by other brands for our brand

    Purapiel

    Purapiel Boot Botspring3 Brown

    £189.99£99.9547% Off
  43. Gear up for adventure with our Colton boot. This design features our signature stacked coloured insert heel and a lace up fastening ending in hook fastenings. Crafted from leather the addition of the contrasting padded cuffs adds all-day comfort.

    Dune London

    Dune Mens Colton - Lace Up Hiker Boot

    £130.00£65.0050% Off
  44. Command the city streets in these rich brown leather brogue Chelsea boots, where classic craftsmanship meets modern versatility. Whether youre stepping into a high-stakes meeting or winding down at a weekend dinner, these boots are your effortless go-to. Crafted from premium genuine leather, they boast timeless brogue detailing that brings a touch of refinement to their classic stylish looks. The easy slip-on design, paired with dual elasticated gussets, ensures a snug, flexible fit that moves with you. Beneath it all, a high-grip rubber sole provides dependable traction on any terrain. -Leather upper -Brogue detailing - Twin gusset design - Dual pull tab and slip on design for easy on / off wear - Slight raised heel - Rugged durable rubber outsole - Catesby branding

    Catesby

    Catesby Engand Sandhurst Mens Leather Brogue Boots

    £129.99£44.4966% Off
  45. A classic Chelsea boot featuring elastic for easy on and off, a soft microfibre lining, and comfy foam footbed, the Russell is a great every day pick for comfort and style

    Hush Puppies

    Hush Puppies Russell Leather Men's Black Boots

    £95.00£69.0927% Off
  46. The Pax are a navy suede ankle boot with two black elasticated panels at the ankle. The black and red tab at the back of the ankle aids slip on ability.

    KG Kurt Geiger

    KG Kurt Geiger Suede Pax Boots

    £129.00£79.0039% Off
  47. A Classic Desert Style Boot with a Double Elastic Gusset; the Samuel Boot is built with a Worry Free Water Repellent leather upper and a flexible yet lightweight sole unit. Its breathable textile and sock lining keeps wearer dry and comfy

    Hush Puppies

    Hush Puppies Shaun Leather Men's Waxy Brown Boots

    £75.00£55.0427% Off
  48. The Catesby England Andrew Chelsea boot is crafted from high-quality leather, delivering its individual profile with a subtle heel. High quality leather uppers are moulded into a simple, yet effective Chelsea ankle boot upper with a elasticated side panel to provide both an easy on / off application, assisted by a pull tab on the ankle delivering an extremely comfortable fit. - Premium Leather Upper - Elasticated side gussets - Heel Tab for easy on / off wear - Comfort Flex insole - Durable rubber outsole

    Catesby

    Catesby England Andrew Leather Mens

    £79.99£59.0526% Off