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| Best Seller  | Classic 550 Series Water Resistant Chelsea Boot Men's Blundstone Classic 550 Series Water Resistant Chelsea Boot - Brown - Casual boots Premium, water-resistant leather elevates a ruggedly built Chelsea boot featuring shock-absorbing PORON® XRD cushioning in the heel to reduce impact fatigue. more | FREE shipping go to store |
 | Men's Blundstone Classic Chelsea Boot - Brown - Casual boots A Chelsea boot made from durable leather with signature SPS Max Comfort System technology keeps your feet protected and supported day in and out. more | FREE shipping go to store |
| Best Seller  | Men's Church's Classic Chelsea Boots - Brown - Casual boots Dimensions: Heel: 3cm, Height: 12cm, Sole: 1cm 100% Suede, 100% Leather, 100% Rubber. Made in United Kingdom. more | $1,047.32 $754.07 FREE shipping go to store |
 | J.Crew Chelsea Boots Black Leather Ankle Heel Classic 9 $250. Excellent Condition Minimal Wear Size 9 Original Box Included Wardrobe Staple Style Similar To Saint Laurent Ysl Wyatt Boots more | go to store |
 | Ralph Lauren Brown Leather Chelsea Boot Size 8 more | go to store |
 | Madewell Shoes | Madewell Regan Chelsea Ankle Boots Classic | Color: Black | Size: 7 Madewell Size 7 Regan Chelsea Ankle Boots W/ A Moderate 2.5” Heel Classic Style Slip On W/ Elastic Side Goring & Pull Tabs In Great Used Condition With Minimal Wear To Leather Upper & Lots Of Life Left. Leather Lined. Made To Last! Boho Bihemian... more | go to store |
 | Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 8.5 GB00353-085W Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 8.5 GB00353-085W. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on the... more | FREE shipping go to store |
 | Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Wide Brown 10.5 GB00353-105W. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on the... more | FREE shipping go to store |
 | Georgia Boot AMP LT Wedge Steel Toe Waterproof Chelsea Work Boot - Men's Medium Brown 10.5 GB00353-105M. The new Georgia Boot AMP LT Wedge Work Boots start out with durable pasture proof SPR leather just like their classic wedges but then we pack on... more | FREE shipping go to store |
 | Renegade Chelsea Boot - Brown - Florsheim Boots Men's Florsheim Renegade Chelsea Boot - Brown - Casual boots Bolster your chilly weather wardrobe with the Renegade Chelsea boot from Florsheim. This sharp boot sports a leather design and classic look that makes for a versatile add. Leather upper.... more | FREE shipping go to store |
 | Florsheim Lodge Plain Toe Gore Boot - Mens 9 Black Boot Medium *This boot combines modern materials and comfort technology with the classic Chelsea boot design *Leather upper *Pull-on styling with side gores *Fully cushioned Ortholite footbed *Rubber outsole more | FREE shipping go to store |
 | Florsheim Lodge Plain Toe Gore Boot - Mens 7 Black Boot Medium *This boot combines modern materials and comfort technology with the classic Chelsea boot design *Leather upper *Pull-on styling with side gores *Fully cushioned Ortholite footbed *Rubber outsole more | FREE shipping go to store |
 | Florsheim Lodge Plain Toe Gore Boot - Mens 13 Black Boot Medium *This boot combines modern materials and comfort technology with the classic Chelsea boot design *Leather upper *Pull-on styling with side gores *Fully cushioned Ortholite footbed *Rubber outsole more | FREE shipping go to store |
 | Brooks Brothers Men's Leather Chelsea Boots | Cognac | Size 10½ D The classic shoes of rock stars, pop-art stars and style stars gets the Brooks Brothers treatment with exceptional construction and genuine leather details throughout. Put your best foot forward. Leather sole, leather stacked heel; tonal stitching100%... more | go to store |
 | Brooks Brothers Men's Leather Chelsea Boots | Cognac | Size 10 D The classic shoes of rock stars, pop-art stars and style stars gets the Brooks Brothers treatment with exceptional construction and genuine leather details throughout. Put your best foot forward. Leather sole, leather stacked heel; tonal stitching100%... more | go to store |
 | Brooks Brothers Men's Leather Chelsea Boots | Cognac | Size 9 D The classic shoes of rock stars, pop-art stars and style stars gets the Brooks Brothers treatment with exceptional construction and genuine leather details throughout. Put your best foot forward. Leather sole, leather stacked heel; tonal stitching100%... more | go to store |
 | Blundstone Classic 550 Chelsea Boots Men's J.Crew Blundstone Classic 550 Chelsea Boots - Brown - Casual boots Famously rugged, Blundstone boots are built to withstand just about anything and everything you throw at them (originally designed for ranchers in the Australian outback, they'll... more | go to store |
 | Men's Dune Character Chelsea Boot - Brown - Casual boots Shaped from creamy leather, this classic Chelsea boot is always in style. more | FREE shipping go to store |
 | Men's Dune Character Chelsea Boot - Black - Casual boots Shaped from creamy leather, this classic Chelsea boot is always in style. more | FREE shipping go to store |
 | Men's Barbour Farsley Chelsea Boot - Brown - Casual boots Burnished leather elevates a stylish Chelsea boot with clean, classic appeal. more | FREE shipping go to store |
 | Men's Ferragamo Chelsea Boot - Black - Casual boots Equestrian vibe with a contemporary finish, the classic Chelsea boot is given the Ferragamo touch. The leather is buffed for a high shine finish, punctuated by narrow elastic strips at the ankle. The... more | $1,150.00 $691.00 FREE shipping go to store |
 | Men's Frye Tyler Chelsea Boot - Brown - Formal boots Stretchy side panels and a back pull-tab mean easy entry into this classic Chelsea boot made from smooth and buttery leather. more | FREE shipping go to store |
 | Men's Mezlan Warden Chelsea Boot - Black - Casual boots A structured toe adds a handsome touch to this classic Chelsea boot built with elastic gore insets and a cushioned footbed with orthotic support. Pull-on style with elastic gore insets Cushioned... more | FREE shipping go to store |
 | Men's Steve Madden Vexin Chelsea Boot - Black - Casual boots Add the Vexin Chelsea boots to your closet for an everyday staple piece. This pair from Steve Madden features a classic silhouette that is easy to style and sophisticated stitching for a... more | FREE shipping go to store |
 | Men's Frye Tyler Chelsea Boot - Black - Casual boots Keep your look classic with a handcrafted Chelsea boot designed for a flexible fit and everyday comfort thanks to rubber insets in the leather sole. Pull-on style with elastic gore insets Leather... more | FREE shipping go to store |
 | Men's Ferragamo Chelsea Boot - Black - Casual boots Equestrian vibe with a contemporary finish, the classic Chelsea boot is given the Ferragamo touch. The leather is buffed for a high shine finish, punctuated by narrow elastic strips at the ankle. The... more | $1,150.00 $691.00 FREE shipping go to store |
 | Men's Mix No 6 Daxon Chelsea Boot - Black - Casual boots Go for a classic look when you wear the Daxon Chelsea boots from Mix No. 6. The timeless silhouette will match with a multitude of different looks, while the memory foam insole provides all-day... more | go to store |
 | Men's Vagabond Percy Chelsea Boot - Black - Casual boots Goring side panels and a rear pull tab lend classic elements to a smooth leather Chelsea boot that will refine your desk-to-dinner style. more | FREE shipping go to store |
 | Men's Vagabond Percy Chelsea Boot - Brown - Casual boots Goring side panels and a rear pull tab lend classic elements to a smooth leather Chelsea boot that will refine your desk-to-dinner style. more | FREE shipping go to store |
 | Men's Thomas & Vine Watson Chelsea Boot - Brown - Casual boots Take the classic route to your suave styling with the Thomas & Vine Watson Chelsea boot. The wingtip toe with brogue detailing provides a timeless look, while the memory foam insole ensures... more | FREE shipping go to store |
 | Men's Tod's Leather Chelsea Boots - Black - Casual boots Chelsea boots are an enduring classic in any wardrobe. Tod's version is made from polished leather stamped with the brand's monogram and rubber pebble detailing on the heel. Wear them with... more | FREE shipping go to store |
 | Men's Tod's Chelsea Boot - Brown - Casual boots Classic Chelsea style defines this suave boot crafted in velvety calfskin suede that's stamped at the side with the label's logo and set on a pebbled sole. Pull-on style with elastic gore insets Leather... more | FREE shipping go to store |
 | Men's Vagabond Alex M Chelsea Boot - Black - Casual boots Goring panels and a rear pull tab lend classic elements to a smooth leather Chelsea boot outfitted with a modern almond toe and sturdy rubber sole. more | FREE shipping go to store |
 | Men's Vince Camuto Huntsley Chelsea Boot - Brown - Casual boots Add classic appeal to your look with the Huntsley Chelsea boot from Vince Camuto. This pull-on boot is made of rich leather for added style and durability and designed with elastic gore... more | $119.99 $89.98 FREE shipping go to store |
 | Men's To Boot New York Shawn Chelsea Boot - Brown - Casual boots Classic Chelsea style defines this handsome suede ankle boot furnished with an arch-supporting cushioned footbed for superior comfort. Pull-on style with elastic gore insets Cushioned... more | FREE shipping go to store |
 | Men's Vince Camuto Huntsley Chelsea Boot - Black - Casual boots Add classic appeal to your look with the Huntsley Chelsea boot from Vince Camuto. This pull-on boot is made of rich leather for added style and durability and designed with elastic gore... more | $119.99 $89.98 FREE shipping go to store |
 | 2976 Wintergrip Water Resist Chelsea Boot At Nordstrom Men's Dr. Martens 2976 Wintergrip Water Resist Chelsea Boot At Nordstrom - Brown - Casual boots This classic Chelsea boot is ready for snowy weather with a water- and salt-resistant leather upper, cozy fleece lining and sturdy, traction-enhancing sole. more | $190.00 $114.00 FREE shipping go to store |
 | Men's Taft The Jude Chelsea Boot - Brown - Casual boots A plush, velvety finish refines the look of a classic Chelsea boot grounded by a lightly cushioned footbed. Pull-on style with elastic gore insets Textile upper/leather lining/rubber sole Made in... more | FREE shipping go to store |
 | Men's Frye Tyler Chelsea Boot - Brown - Casual boots Go for a classic look with this handcrafted Chelsea boot designed for a flexible fit and everyday comfort thanks to rubber insets in the leather sole. Pull-on style with elastic gore insets... more | FREE shipping go to store |
 | Men's Thomas & Vine Watson Chelsea Boot - Brown - Casual boots Take the classic route to your suave styling with the Thomas & Vine Watson Chelsea boot. The wingtip toe with brogue detailing provides a timeless look, while the memory foam insole ensures... more | FREE shipping go to store |
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