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Chukka Boots

These chukka boots were made for walking! These versatile ankle boots can be worn to the office or on the weekends. Transform any outfit with an effortlessly stylish pair.

Looking to change up your choice of work shoes? Consider incorporating chukka boots to your workweek rotation. Keep it simple and sleek with black leather boots. A plain toe front pairs perfectly with a suit or dress pants in a formal office setting. If you love the ease of slip-on shoes, Steve Madden boots are styled like loafers but with a higher top. Prefer the classic look of lace-ups instead? Clarks offers leathers boots with a textured rubber sole—great for slick weather. Go from the office straight to happy hour with dashing chukka boots. Opt for the smooth feel of Calvin Klein brown suede boots or a pair of Stacy Adams boots in tan.

Hang with the boys on the weekend in casual boots from Levi’s. A pair from Fossil combines the clean lines of dress shoes with a rustic feel. Rock the streets in Timberland boots and prep for cold weather with a cozy shearling lining. Hugo Boss offers the timeless design of men’s boots with the added detail of weathered suede. If comfort is a high priority, Hush Puppies shoes feature a unique contoured footbed for ultimate support—while staying ever so stylish. Or try a pair of sneaker inspired boots from Nike.

There’s no need to break out those clunky shoes for harsh weather. Brave the rain in waterproof chukka boots from and Sebago. With the traction sole of Cole Haan boots, you’re sure to stay grounded even in a snowstorm. Taking to fishing trip? Sperry offers boots with the look and feel of boat shoes.

For work and for play, chukka boots stylishly fit in any setting. Check out the selection of great men’s shoes at Macy’s today.

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  • 29 items in Chukka Boots

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      Steve Madden Harken Chukka Boots
      $90.00
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      (177)
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      Clarks Men's Bushacre 2 Chukka Boot
      $100.00
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      (123)
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      Rockport Men's Classic Break Chukka Boot
      $135.00
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      (32)
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      Kenneth Cole Reaction Desert Sun Suede Chukkas
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      $98.00
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      (3)
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      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      $98.00
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      (62)
    • Calvin Klein Men's Bain Saffiano Chukka Boots
      $115.00
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    • G. H. Bass & Co. Men's Bennett Chukka Boots
      $110.00
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      (2)
    • Frye Men's Scott Chukka Boots, Created for Macy's
      $228.00
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      Kenneth Cole Reaction Desert Sun Suede Chukkas
      $98.00
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      (150)
    • 2 colors
      Kenneth Cole Reaction Men's Desert Sun Perforated Chukka Boots
      $98.00
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    • Kenneth Cole Reaction Men's Desert Sun Textured Suede Chukka Boots
      $98.00
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    • UGG® Men's Freamon Leather Chukka Boots
      $150.00
      Now $97.50
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      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      $98.00
      Now $63.70
      Spend $100, get $40 off
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      (2)
    • Frye Men's Scott Suede Chukka Boots, Created for Macy's
      $228.00
      Now $148.20
      Spend $100, get $40 off
      Enjoy $40 off when you spend $100 on select styles
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      New markdown
      Prices just reduced - Limited Quantities
      New markdown
    • Kenneth Cole Reaction Desert Sun Suede Chukkas
      $98.00
      Now $63.70
      Spend $100, get $40 off
      Enjoy $40 off when you spend $100 on select styles
      Spend $100, get $40 off
      (20)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Suede Chukkas
      $98.00
      Now $63.70
      Spend $100, get $40 off
      Enjoy $40 off when you spend $100 on select styles
      Spend $100, get $40 off
      (1)
    • Calvin Klein Men's Albe Nappa Leather Chukka Boots
      $150.00
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    • Stacy Adams Men's Delaney Chukka Boots
      $105.00
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      (14)
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      NEW! Alfani Men's Jason Suede Chukka Boots, Created for Macy's
      $99.99
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    • 2 colors
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    • Alfani Men's Aiden Chukka Boot Created for Macy's
      $59.99
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      (16)
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