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Hello, Fall: Desert Boots!
These mid-top marvels deliver sneaker-caliber comfort, but with a more polished vibe. Chukka boots manage to fit in to happy hour, date night and weekend looks, while standing out in a sea of tired kicks. Choose from polished, sueded, moc-toe and more—and enjoy the upgrade.

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  • Frank Wright Men's Smith Chukka Boot


    Frank Wright Men’s Smith Chukka Boot

    $140.0$59.0

  • Gorilla USA Men's Chukka Boot


    Gorilla USA Men’s Chukka Boot

    $450.0$179.0

  • Robert Wayne Men's Roma Chukka


    Robert Wayne Men’s Roma Chukka

    $120.0$60.0

  • John Varvatos Men's Star S Eva Chukka


    John Varvatos Men’s Star S Eva Chukka

    $228.0$109.0

  • John Varvatos Men's Star S Eva Chukka


    John Varvatos Men’s Star S Eva Chukka

    $228.0$109.0

  • Original Penguin Men's Birdie Lite Chukka


    Original Penguin Men’s Birdie Lite Chukka

    $140.0$65.0

  • John Varvatos Men's Star Casual Chukka


    John Varvatos Men’s Star Casual Chukka

    $228.0$109.0

  • Rogue Men's Bud Chukka Boot


    Rogue Men’s Bud Chukka Boot

    $295.0$109.0

  • Andrew Marc Men's Dorchester Chukka Boot


    Andrew Marc Men’s Dorchester Chukka Boot

    $178.0$89.0

  • Andrew Marc Men's Dorchester Chukka Boot


    Andrew Marc Men’s Dorchester Chukka Boot

    $178.0$89.0

  • Donald J Pliner Men's Brady Chukka Boot


    Donald J Pliner Men’s Brady Chukka Boot

    $375.0$175.0

  • Donald J Pliner Men's Brady-80 Chukka Boot


    Donald J Pliner Men’s Brady-80 Chukka Boot

    $375.0$175.0

  • Donald J Pliner Men's Brady-80 Chukka Boot


    Donald J Pliner Men’s Brady-80 Chukka Boot

    $375.0$175.0

  • French Connection Men's Corian Chukka Boot


    French Connection Men’s Corian Chukka Boot

    $158.0$75.0

  • Gorilla USA Men's Chukka Boot


    Gorilla USA Men’s Chukka Boot

    $450.0$169.0

  • Gorilla USA Men's Chukka Boot


    Gorilla USA Men’s Chukka Boot

    $450.0$189.0

  • Gorilla USA Men's Chukka Boot


    Gorilla USA Men’s Chukka Boot

    $450.0$179.0

  • French Connection Men's Corian Chukka Boot


    French Connection Men’s Corian Chukka Boot

    $158.0$75.0

  • Tod's Men's Dress Chukka Boot


    Tod’s Men’s Dress Chukka Boot

    $595.0$375.0

  • J. Artola Men's Chuck Chukka


    J. Artola Men’s Chuck Chukka

    $225.0$105.0

  • J. Artola Men's Chuck Chukka


    J. Artola Men’s Chuck Chukka

    $225.0$105.0

  • J. Artola Men's Chuck Chukka


    J. Artola Men’s Chuck Chukka

    $225.0$105.0

  • Steve Madden Men's Garisonn Chukka Boot


    Steve Madden Men’s Garisonn Chukka Boot

    $115.0$59.0

  • Steve Madden Men's Garisonn Chukka Boot


    Steve Madden Men’s Garisonn Chukka Boot

    $115.0$59.0

  • Jose Real Men's Amsterdam Chukka Boot With Brogue Detail


    Jose Real Men’s Amsterdam Chukka Boot With Brogue Detail

    $398.0$189.0

  • Andrew Marc Men's Dorchester Chukka


    Andrew Marc Men’s Dorchester Chukka

    $178.0$41.0

  • Joe's Men's Slick Chukka Boot


    Joe’s Men’s Slick Chukka Boot

    $175.0$85.0

  • Joe's Men's Slick Chukka Boot


    Joe’s Men’s Slick Chukka Boot

    $175.0$85.0

  • Steve Madden Men's Halloway Canvas & Leather Chukka


    Steve Madden Men’s Halloway Canvas & Leather Chukka

    $90.0$39.0

  • Andrew Marc Men's Dorchester Chukka


    Andrew Marc Men’s Dorchester Chukka

    $178.0$41.0

  • Tod's Men's Dress Chukka Boot


    Tod’s Men’s Dress Chukka Boot

    $580.0$375.0

  • Quiksilver Men's Marquez Low Chukka Boot


    Quiksilver Men’s Marquez Low Chukka Boot

    $110.0$52.0

  • John Varvatos Men's Hipster Chukka Boot


    John Varvatos Men’s Hipster Chukka Boot

    $198.0$95.0

  • John Varvatos Men's Star Classic Chukka


    John Varvatos Men’s Star Classic Chukka

    $248.0$105.0

  • John Varvatos Men's Star B Chukka


    John Varvatos Men’s Star B Chukka

    $248.0$125.0

  • Timberland Men's Chukka Midrise Boot


    Timberland Men’s Chukka Midrise Boot

    $185.0$93.0

  • Frank Wright Men's Totton Suede Chukka Boot


    Frank Wright Men’s Totton Suede Chukka Boot

    $120.0$55.0

  • Von Dutch Men's Toolbox Chukka Boot


    Von Dutch Men’s Toolbox Chukka Boot

    $155.0$75.0

  • Von Dutch Men's Toolbox Chukka Boot


    Von Dutch Men’s Toolbox Chukka Boot

    $155.0$75.0

  • Von Dutch Men's Toolbox2 Chukka Boot


    Von Dutch Men’s Toolbox2 Chukka Boot

    $144.0$65.0

  • Frank Wright Men's Totton Suede Chukka Boot


    Frank Wright Men’s Totton Suede Chukka Boot

    $120.0$55.0

  • Robert Wayne Men's Double Gore Chukka


    Robert Wayne Men’s Double Gore Chukka

    $120.0$49.0

  • Andrew Marc Men's Howard Chukka Boot


    Andrew Marc Men’s Howard Chukka Boot

    $148.0$56.0

  • Frank Wright Men's Totton Suede Chukka Boot


    Frank Wright Men’s Totton Suede Chukka Boot

    $120.0$55.0

  • Frank Wright Men's Totton II Chukka Boot


    Frank Wright Men’s Totton II Chukka Boot

    $130.0$59.0

  • Robert Graham Men's Bedford Casual Cap Toe Chukka


    Robert Graham Men’s Bedford Casual Cap Toe Chukka

    $328.0$155.0

  • Timberland Men's Brasstown Chukka


    Timberland Men’s Brasstown Chukka

    $110.0$49.0

  • Bacco Bucci Men's Vialli Suede Chukka Boot


    Bacco Bucci Men’s Vialli Suede Chukka Boot

    $265.0$125.0

  • Rockport Men's Ledge Hill Too Chukka Boot


    Rockport Men’s Ledge Hill Too Chukka Boot

    $150.0$59.0

  • Pointer Footwear Men's Surfer Rosa Mid Chukka Boot


    Pointer Footwear Men’s Surfer Rosa Mid Chukka Boot

    $140.0$59.0

  • Vlado Men's Valentino-Mid Chukka Sneaker


    Vlado Men’s Valentino-Mid Chukka Sneaker

    $130.0$58.0

  • Andrew Marc Men's Parkchester Chukka Boot


    Andrew Marc Men’s Parkchester Chukka Boot

    $178.0$55.0

  • Steve Madden Men's Harsen Leather Chukka


    Steve Madden Men’s Harsen Leather Chukka

    $90.0$39.0

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