Men's Red Wing Classic Chelsea
$239.99$299.99Chelsea Boots Men's — February 2026
Curated selection of Chelsea Boots Men's pulled from our shop in February 2026. Explore listings, transparent pricing, and merchant details in one place.
Timberland Men's Redwood Falls Chelsea
$104.00$130.00
Thursday Boot Company Men's Leather Legend Chelsea
$159.20$199.00
To Boot New York Men's Largo Waxed Suede Chelsea Boots
$396.00$495.00
Men's Red Wing Heritage Classic Chelsea
$239.99$299.99
Allen Edmonds Men's Liverpool Chelsea Boot
$440.00$550.00
Quince Men's Essential Leather Chelsea Boot
$120.00$150.00
Thursday Boot Company Men's Suede Cavalier Chelsea
$159.20$199.00
Beckett Simonon Bolton Chelsea Boots
$215.20$269.00
Sorel Men's Cyprus Chelsea Waterproof Boot
$100.00$125.00
Hunter Men's Landon Waterproof Chelsea Boots
$152.00$190.00
Cole Haan Men's Roundhill Grand Waterproof Chelsea Boots
$167.96$209.95
Blundstone Men's Boots
$175.96$219.95
Thursday Boot Company Men's Duke Leather Chelsea
$159.20$199.00
Blundstone 585 Chelsea Boots
$167.96$209.95
Kenneth Cole Men's Tully Chelsea Boots
$148.00$185.00
Cole Haan Men's Judson Grand Chelsea Boots
$143.96$179.95
Carlos by Carlos Santana Men's Mantra Chelsea Boots
$127.20$159.00
Blundstone 558 Chelsea
$167.96$209.95
Men's Cervantes Chelsea Mezlan
$238.00$297.50
Ariat Men's Wexford Waterproof Boots
$167.96$209.95
Frye Men's Tyler Flex Chelsea Boots
$206.40$258.00
Hunter Boots Men's Refined Slim Fit Chelsea Boots
$140.00$175.00
Florsheim Men's Forge Plain Toe Gore Boot
$104.00$130.00
TAFT Men's Murphy Leather Chelsea Boots
$279.20$349.00
Forsake Men's Phil Waterproof Chelsea Boots
$116.00$145.00
Blundstone 587 Chelsea Boots
$167.96$209.95
J.Crew Men's Kenton Chelsea Boots
$262.40$328.00
Timberland Men's Britton Road Chelsea Boot
$128.00$160.00
L.L. Bean Men's Storm Chaser Chelsea Boots
$136.00$170.00