Men's Boots and Chukkas

15 Item(s) Total
  • The Men's Combat Boot 84

    KENNETH COLE NEW YORK
    $295.00
    FREE SHIPPING ELIGIBLE
    30% OFF AT CHECKOUT
  • + More Colors

    Bainx Short Combat Boot with Suede Collar

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $69
    30% OFF AT CHECKOUT
  • + More Colors

    Aaron Side Zip Waxed Leather Ankle Boot

    KENNETH COLE NEW YORK
    $175.00
    FREE SHIPPING ELIGIBLE
    30% OFF AT CHECKOUT
  • Moto Strap Harness Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $74
    30% OFF AT CHECKOUT
  • + More Colors

    Roll Wool Collar Lace Up Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $74
    30% OFF AT CHECKOUT
  • Nation Neoprene Sock Sneaker Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $74
    30% OFF AT CHECKOUT
  • + More Colors

    Blind Sided Wingtip Oxford Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $69
    30% OFF AT CHECKOUT
  • Half N Half Saffiano Chelsea Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $69
    30% OFF AT CHECKOUT
  • + More Colors

    Guy Leather Chelsea Boot

    REACTION KENNETH COLE
    $130.00
    FREE SHIPPING ELIGIBLE
    NOW $94
    30% OFF AT CHECKOUT
  • + More Colors

    Desert Sun Leather Chukka Boot

    REACTION KENNETH COLE
    $95.00
    FREE SHIPPING ELIGIBLE
    NOW $69
    30% OFF AT CHECKOUT
  • + More Colors

    Ap-Plause Chukka Boot

    REACTION KENNETH COLE
    $118.00
    FREE SHIPPING ELIGIBLE
    NOW $74
    30% OFF AT CHECKOUT
  • Textile Wrap Boot with Lug Sole

    REACTION KENNETH COLE
    $95.00
    FREE SHIPPING ELIGIBLE
    30% OFF AT CHECKOUT
  • Mix Zip Up Leather Boot

    KENNETH COLE NEW YORK
    $175.00
    FREE SHIPPING ELIGIBLE
    30% OFF AT CHECKOUT
  • + More Colors

    Upper Cut High-Top Boot

    UNLISTED, A KENNETH COLE PRODUCTION
    $95.00 $34.98
    FREE SHIPPING ELIGIBLE
    30% OFF AT CHECKOUT
    CLEARANCE - FINAL SALE
  • + More Colors

    Beat It Lace-Up Boot

    REACTION KENNETH COLE
    $120.00 $44.98
    FREE SHIPPING ELIGIBLE
    30% OFF AT CHECKOUT
    CLEARANCE - FINAL SALE
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.