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Shop by Style: The Chelsea Boot!
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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  • Antonio Maurizi Men's 7344 Wingtip Chelsea Boot (Black)


    Antonio Maurizi Men’s 7344 Wingtip Chelsea Boot (Black)

    $695$279.00

  • Antonio Maurizi Men's 7344 Wingtip Chelsea Boot (T.moro)


    Antonio Maurizi Men’s 7344 Wingtip Chelsea Boot (T.moro)

    $695$279.00

  • Andrew Marc Men's Monroe Boot (Brown)


    Andrew Marc Men’s Monroe Boot (Brown)

    $128$59.00

  • Bacco Bucci Men's Bareda Boot (Brown)


    Bacco Bucci Men’s Bareda Boot (Brown)

    $250$125.00

  • Antonio Maurizi Men's Pasquale Boot (Brown-Brucato)


    Antonio Maurizi Men’s Pasquale Boot (Brown-Brucato)

    $650$249.00

  • Andrew Marc Men's Chelsea Boot (Black)


    Andrew Marc Men’s Chelsea Boot (Black)

    $178$89.00

  • Andrew Marc Men's Chelsea Boot (Espresso)


    Andrew Marc Men’s Chelsea Boot (Espresso)

    $178$89.00

  • Andrew Marc Men's Chelsea Boot (Tobacco)


    Andrew Marc Men’s Chelsea Boot (Tobacco)

    $178$89.00

  • Bacco Bucci Men's Dafine Ankle Boot (Black)


    Bacco Bucci Men’s Dafine Ankle Boot (Black)

    $275$139.00

  • Bacco Bucci Men's Dafine Ankle Boot (Brown)


    Bacco Bucci Men’s Dafine Ankle Boot (Brown)

    $275$139.00

  • Bacco Bucci Men's Costa Ankle Boot (Black)


    Bacco Bucci Men’s Costa Ankle Boot (Black)

    $210$105.00

  • Bacco Bucci Men's Renzo Ankle Boot (Black)


    Bacco Bucci Men’s Renzo Ankle Boot (Black)

    $255$129.00

  • Bacco Bucci Men's Renzo Ankle Boot (Brown)


    Bacco Bucci Men’s Renzo Ankle Boot (Brown)

    $255$129.00

  • Billy Reid Men's Beatty Boot (Brown)


    Billy Reid Men’s Beatty Boot (Brown)

    $450$215.00

  • Gordon Rush Collection Men's Flynn Double-Gored Boot (Black)


    Gordon Rush Collection Men’s Flynn Double-Gored Boot (Black)

    $445$220.00

  • JD Fisk Men's Neal Boot (Black nubuck)


    JD Fisk Men’s Neal Boot (Black nubuck)

    $219$95.00

  • JD Fisk Men's Mathers Boot (Black)


    JD Fisk Men’s Mathers Boot (Black)

    $199$99.00

  • JD Fisk Men's Mathers Boot (Brown)


    JD Fisk Men’s Mathers Boot (Brown)

    $199$99.00

  • JD Fisk Men's Franky Boot (Black Leather)


    JD Fisk Men’s Franky Boot (Black Leather)

    $219$95.00

  • JD Fisk Men's Franky Boot (Chocolate Leather)


    JD Fisk Men’s Franky Boot (Chocolate Leather)

    $219$95.00

  • Kenneth Cole New York Men's Weekly Meeting Boot (Black)


    Kenneth Cole New York Men’s Weekly Meeting Boot (Black)

    $168$84.00

  • Kenneth Cole New York Men's Film Star Boot (Brown)


    Kenneth Cole New York Men’s Film Star Boot (Brown)

    $178$99.00

  • Roberto Cavalli Men's Side Zip Boot (Black)


    Roberto Cavalli Men’s Side Zip Boot (Black)

    $560$250.00

  • Rockport Men's Fairwood 2 Chelsea Boot (Black)


    Rockport Men’s Fairwood 2 Chelsea Boot (Black)

    $150$35.00

  • Rockport Men's Fairwood Ankle Boot (Dark Brown Scrunch)


    Rockport Men’s Fairwood Ankle Boot (Dark Brown Scrunch)

    $140$59.00

  • Steve Madden Men's Bannir Dress Boot (Black Leather)


    Steve Madden Men’s Bannir Dress Boot (Black Leather)

    $70$48.00

  • testoni BASIC Men's Chelsea Boot (Nero)


    testoni BASIC Men’s Chelsea Boot (Nero)

    $675$225.00

  • testoni BASIC Men's Chelsea Boot (T Moro)


    testoni BASIC Men’s Chelsea Boot (T Moro)

    $675$225.00

  • Tod's Men's Ankle Boot (Nero)


    Tod’s Men’s Ankle Boot (Nero)

    $650$349.00

  • Tod's Men's Side-Zip Boot (Testa Moro)


    Tod’s Men’s Side-Zip Boot (Testa Moro)

    $670$375.00

  • Tod's Men's Ankle Boot (Testa Moro)


    Tod’s Men’s Ankle Boot (Testa Moro)

    $670$375.00

  • Wolverine No. 1883 Men's Hartley Chelsea Boot (Black)


    Wolverine No. 1883 Men’s Hartley Chelsea Boot (Black)

    $135$69.00

  • Wolverine No. 1883 Men's Hartley Chelsea Boot (Dark Brown)


    Wolverine No. 1883 Men’s Hartley Chelsea Boot (Dark Brown)

    $135$69.00

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