Men's Boots and Chukkas

56 Item(s) Total
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    Donnie Buckle Strap Chelsea Boot

    KENNETH COLE NEW YORK
    $175.00
    LIMITED TIME $89
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    Donnie Buckle Strap Chelsea Boot

    KENNETH COLE NEW YORK
    $175.00
    LIMITED TIME $89
  • Stamp Leather Chukka Boot

    KENNETH COLE NEW YORK
    $160.00
    LIMITED TIME $79
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    Rocketpod Leather Chukka Sneaker with Techni-Cole

    KENNETH COLE NEW YORK
    $150.00
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    Rocketpod Leather Chukka Sneaker with Techni-Cole

    KENNETH COLE NEW YORK
    $150.00
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    Rocketpod Leather Chukka Sneaker with Techni-Cole

    KENNETH COLE NEW YORK
    $150.00
  • Zac Chelsea Boot

    REACTION KENNETH COLE
    $125.00
    LIMITED TIME $69
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    Uptown Suede Chukka Boot

    REACTION KENNETH COLE
    $110.00
    RULE BREAKER PRICE $49
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    Uptown Suede Chukka Boot

    REACTION KENNETH COLE
    $110.00
    RULE BREAKER PRICE $49
  • Whistler Suede Chelsea Boot

    KENNETH COLE NEW YORK
    $195.00
    LIMITED TIME $89
  • Hugh Cap Toe Lace Up Boot

    KENNETH COLE NEW YORK
    $195.00
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    Klay Wingtip Oxford Boot

    REACTION KENNETH COLE
    $145.00
    RULE BREAKER PRICE $69
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    Klay Wingtip Oxford Boot

    REACTION KENNETH COLE
    $145.00
    RULE BREAKER PRICE $69
  • The Men's Combat Boot 84

    KENNETH COLE NEW YORK
    $295.00
  • Aaron Side Zip Waxed Leather Ankle Boot

    KENNETH COLE NEW YORK
    $175.00
  • Suede Ankle Boot

    KENNETH COLE NEW YORK
    $195.00
    LIMITED TIME $84
  • Moto Strap Harness Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    RULE BREAKER PRICE $39
  • Nation Neoprene Sock Sneaker Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    RULE BREAKER PRICE $39
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    Stand Sport Chukka Sneaker

    UNLISTED, A KENNETH COLE PRODUCTION
    $80.00
    RULE BREAKER PRICE $34
  • The Mover High Top Sneaker Boot

    KENNETH COLE NEW YORK
    $160.00
    LIMITED TIME $99
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    Stand Sport Chukka Sneaker

    UNLISTED, A KENNETH COLE PRODUCTION
    $80.00
    RULE BREAKER PRICE $34
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    Brand Tour Mid Leather Sneaker

    KENNETH COLE NEW YORK
    $165.00
    LIMITED TIME $89
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    Brand Tour Mid Leather Sneaker

    KENNETH COLE NEW YORK
    $165.00
    LIMITED TIME $89
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    Tonal Leather Chukka Boot

    KENNETH COLE NEW YORK
    $175.00
    LIMITED TIME $109
Men’s boots for the modern uniform.

An excellent pair of a men’s boots is a powerful investment in the rest of your wardrobe. Boots can feel rugged or refined. Chelsea boots look smart and sleek paired with tailored and formal looks, but they’re a comfortable classic that ups the taste of your casual look with jeans. A short, laidback chukka in brown leather or black suede feels right at home with workwear and on relaxed nights. Your staple boot says a lot about you, so keep it versatile and pick up several styles. Elegant pull-on dress boots, lace-up combat and military boots, ankle boots, fashion boots. Wingtip dress boots with perforated details in genuine leather, or waterproof boots for a weather-resistant winter commute. Whatever you’re looking for, boots for men by Reaction and Kenneth Cole New York are designed to fit your life and enhance your style.

Looking for more formal options? Shop stylish and comfortable dress shoes for men here.