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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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    Chukka Boots

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    • 4 colors
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      Clarks Men's Bushacre 2 Chukka Boots
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      $100.00
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      (28)
    • Alfani Men's Aiden Chukka Boot Created for Macy's
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      $59.99
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    • 3 colors
      Clarks Men's Vargo Apron-Toe Leather Chukka Boots, Created for Macy's
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      $110.00
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    • 2 colors
      Tommy Hilfiger Men's Gervis Chukka Boots
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      $90.00
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    • 2 colors
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      Steve Madden Harken Chukka Boots
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      $90.00
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    • 2 colors
      Rockport Men's Leather Sharp & Ready Chukkas
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      $150.00
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      (1)
    • Extended Widths
      Clarks Men's Bushacre 2 Chukka Boot
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      $100.00
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      (124)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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    • 3 colors
      Calvin Klein Men's Ultan Suede Chukka Boots
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    • Clarks Men's Cotrell Rise Plain-Toe Casual Chukka Boots
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    • 3 colors
      Tommy Hilfiger Men's Laurel Chukka Boots
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      $90.00
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    • 2 colors
      Clarks Men's Grandin Mid Casual Chukka Boots
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      $110.00
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    • Clarks Men's Tilden Top Waterproof Dress Chukka Boots
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      $115.00
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    • 2 colors
      Timberland Men's Richdale Leather Chukka Boots, Created For Macy's
      $140.00
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    • Ecco Men's Turn Gtx Chukka Boots
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      $230.00
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      (8)
    • 2 colors
      Cole Haan Men's Ripley Grand Chukkas
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      $190.00
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    • UGG® Men's Neumel Chukka Boots
      $150.00
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      (16)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
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      $98.00
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    • 2 colors
      Sorel Men's Madson Waterproof Chukka Boots
      $170.00
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