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Initially developed for horse riding, the Chelsea boot has become a fashion icon. These typically snug fitting ankle boots often feature elastic side panels that flex to fit your foot. That makes them easy to put on without sliding around on your foot all day. Even better? They’re incredibly versatile. Pair them with a 3-piece suit for a comfortable work day, or with casual denim for a rugged weekend look.
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Rockport Men’s Fairwood 2 Chelsea Boot (Black)$150$45.00 -
Antonio Maurizi Men’s 7344 Wingtip Chelsea Boot (Black)$695$249.00 -
Antonio Maurizi Men’s 7344 Wingtip Chelsea Boot (T.moro)$695$249.00 -
Antonio Maurizi Men’s Chelsea Boot (Black)$695$279.00 -
Antonio Maurizi Men’s Chelsea Boot (T.moro)$695$279.00 -
Gordon Rush Collection Men’s Flynn Double-Gored Boot (Black)$445$220.00 -
Gordon Rush Made In Italy Men’s Zander Two-Toned Chelsea Boot (Black/Lavagne)$495$248.00 -
Gordon Rush Made In Italy Men’s Zander Two-Toned Chelsea Boot (T.Moro/Paludo)$495$248.00 -
Calvin Klein Men’s Cambell Chelsea Boot (Dark Brown)$180$89.00 -
Calvin Klein Men’s Cambell Chelsea Boot (Black)$180$89.00 -
Eastland Men’s Daily Double Chelsea Boot (Brown)$110$59.00 -
Wolverine No. 1883 Men’s Hartley Chelsea Boot (Black)$135$59.00 -
Andrew Marc Men’s Chelsea Boot (Espresso)$178$69.00 -
Andrew Marc Men’s Chelsea Boot (Tobacco)$178$69.00 -
adidas Y-3 by Yohji Yamamoto Men’s Chelsea Boot (Black/Navy)$450$139.00 -
testoni BASIC Men’s Chelsea Boot (Nero)$675$179.00 -
testoni BASIC Men’s Chelsea Boot (T Moro)$675$179.00 -
John Varvatos Men’s Ronson Side Gore Boot (Espresso)$298$149.00
