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Mens Leather Boots

Looking for that great new cool accent to your work or downtime look? Be it weathered and rugged, smooth and modern, the right leather boot is out there for you.

A Modern Staple

The leather boot is the new men’s wardrobe must-have: Look for sleek styles that take you from work to weekend. A low-top, earth-toned chukka boot from Timberland is the perfect way to look savvy and well-kept from the morning meeting to your evening plans.

Style Asset
The weekend is your opportunity to mix it up! Flex your style muscles with a handsome caramel-hued slip-on number, or a sandy lace-up from Clarks. For your festival-going plans, downtown flair is the name of the game with a black vintage-style combat boot. Waterproofing and gripped soles in cool, handsome styles are what outdoors-geared leather boots are all about.

Check out all of the latest men’s leather boots at Macy’s.

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  • 36 items in Mens Leather Boots

                    
                
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    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (1650)
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
      Sale $79.99
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      (179)
    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (396)
    • Alfani Jack Cap Toe Boots, Created for Macy's
      Limited-Time Special
      $99.99
      Sale $63.99
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      (65)
    • Extended Widths
      Timberland Men's 6" Basic Waterproof Boot
      $145.00
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      (345)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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      (30)
    • HUGO Men's Dress Appeal Zip Boots
      $295.00
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      (2)
    • UGG® Men's Freamon Leather Chukka Boots
      $150.00
      Now $97.50
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    • 3 colors
      Extended Widths
      Stacy Adams Men's Madison Boot
      $135.00
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      (221)
    • 2 colors
      Extended Widths
      Florsheim Men's Duke Bike Toe Ankle Boot
      $135.00
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      (300)
    • Alfani Men's Briar Harness Boots, Created for Macy's
      Limited-Time Special
      $99.99
      Sale $68.99
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    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
      Limited-Time Special
      $125.00 - 130.00
      Sale $109.99
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      (14)
    • UGG® Men's Yucca Waterproof Boots
      $120.00
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      (48)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
      $135.00
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      (32)
    • AlfaTech by Alfani Men's Ansell Double Buckle Boots, Created for Macy's
      Limited-Time Special
      $119.99
      Sale $82.99
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    • Timberland Men's Kendrick Chelsea Boots
      $140.00
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      (15)
    • AlfaTech by Alfani Men's Callan Double Monk Boots, Created for Macy's
      Limited-Time Special
      $119.99
      Sale $82.99
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    • 8 colors
      Extended Widths
      Eastland Men's Seneca Boot
      Limited-Time Special
      $110.00
      Sale $81.99
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      (6)
    • Extended Widths
      Rockport Men's Rugged Bucs H20 Waterproof Plain Toe Boots
      $120.00
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      (85)
    • Bar III Men's Watson Two-Tone Chelsea Boots, Created for Macy's
      Limited-Time Special
      $109.99
      Sale $75.99
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    • Clarks Men's Original Desert Boots
      $130.00
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      (204)
    • UGG® Men's Neumel Chukka Boots
      $140.00
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      (15)
    • 3 colors
      Eastland Daily Double Side-Gore Boots
      $110.00 - 115.00
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