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Men’s Boots

From simple and laidback to smart and tailored, men’s boots look great with almost any outfit. Boots for men will be the style stars of your cool weather wardrobe. Explore our collection of leather, suede and faux leather boots from popular brands.

When buying men’s boots, always keep your individual taste, profession and lifestyle at the forefront of your mind. Take notes as we break down a few popular styles. Let’s start with chukka boots. Hitting at the ankle, lace-up chukkas are absolutely perfect for casual outings.

Is versatility high on your wish list? Pull-on boots can be dressed up or down. Chelsea boots are a classic pull-on style. These ankle boots feature elastic side panels and round toes. Invest in a pair with a rubber sole to help ensure you can wear them during rain or snow. Speaking of battling the elements, don’t forget to add a pair of work and waterproof boots to your collection. Something sleeker? Military and combat boots will bring the edge.

Round out your collection with a pair of dress boots. Look for duos boasting amazing details like wingtips or brogues. Any lace-up style will look amazing when partnered with a suit or a button-up shirt & dress pants.

We’ve only mentioned a few men’s boots offered at Macy’s—be sure to check out our entire footwear collection. Interested in a complete closet refresh? Shop for men’s clothing and accessories, too.

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  • 83 items in Boots

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    • 4 colors
      Extended Widths
      Clarks Men's Bushacre 2 Chukka Boots
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      $100.00
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    • 4 colors
      Timberland Men's Groveton Hi-Top Sneakers
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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
      Steve Madden Men's Jonnie Boots, Created for Macy's
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    • 2 colors
      Stacy Adams Men's Alomar Cap-Toe Chelsea Boots
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      $105.00
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      Timberland Men's 6" Basic Waterproof Boot
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      $145.00
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    • Extended Widths
      Clarks Men's Bushacre 2 Chukka Boot
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      $100.00
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    • Clarks Men's Hinman Mid-High Boots
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      (4)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
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      $135.00
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      (32)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
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      $98.00
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    • G. H. Bass & Co. Men's Bennett Chukka Boots
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      $110.00
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    • 2 colors
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      Kenneth Cole Reaction Desert Sun Suede Chukkas
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      $98.00
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    • Frye Men's Scott Chukka Boots, Created for Macy's
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      $228.00
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    • 2 colors
      Kenneth Cole Reaction Men's Desert Sun Perforated Chukka Boots
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      $98.00
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      (3)
    • 5 colors
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      Eastland Men's Lumber Up Boot
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      $125.00 - 130.00
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    • ALDO Men's Sthephanus Double-Zip Boots
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      $160.00
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    • Kenneth Cole Reaction Men's Desert Sun Textured Suede Chukka Boots
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      $98.00
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    • 3 colors
      G.H. Bass & Co. Men's Buck 2.0 Demi Boots
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      $135.00
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      (1)
    • 2 colors
      Eastland Daily Double Side-Gore Boots
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      $110.00 - 115.00
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      (3)
    • Kenneth Cole Reaction Desert Sun Suede Chukkas
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      $98.00
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    • Eastland Men's Chester Boots
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      $130.00
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    • 2 colors
      Eastland High Fidelity Lace-Up Boots
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      $125.00
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      (1)
    • Tommy Hilfiger Men's Casey Waterproof Duck Boots Created for Macy's
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      $90.00
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      (73)
    • Calvin Klein Men's Albe Nappa Leather Chukka Boots
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      $150.00
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    • Stacy Adams Men's Delaney Chukka Boots
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      $105.00
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      (14)
    • 9 colors
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      Eastland Men's Seneca Boot
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      $110.00
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      (6)
    • Eastland Men's Daily Double Chelsea Boots
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      $110.00
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      (1)
    • 2 colors
      Eastland Men's Jett Boots
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      $140.00
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    • Eastland Men's Lumber Up Boots
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      $125.00
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    • 2 colors
      Eastland Men's Jack Boots
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      $125.00
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    • 2 colors
      Eastland Men's Jayce Boots
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      $140.00
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      (1)
    • Eastland Men's Ethan 1955 Boots
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      $225.00
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      (2)
    • Eastland Men's Chester Boots
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      $130.00
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    • 2 colors
      Extended Widths
      Timberland Men's Mt. Maddsen Waterproof Hiking Boots
      Black Friday Special
      $120.00
      Sale $99.99
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      (331)
    • 2 colors
      Florsheim Men's Beat Plain-Toe Chelsea Gore Boots
      Black Friday Special
      $130.00
      Sale $77.99
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      (48)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      Black Friday Special
      $98.00
      Sale $37.99
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      (2)
    • Kenneth Cole Reaction Men's Desert Sun Boots
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      $98.00
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    • Extended Widths
      Kenneth Cole Reaction Desert Sun Suede Chukkas
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      $98.00
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      (1)
    • 2 colors
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      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
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      (556)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
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    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
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      (392)
    • HUGO Men's Dress Appeal Zip Boots
      $295.00
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      (2)
    • 3 colors
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      Stacy Adams Men's Madison Boot
      $135.00
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      (164)
    • Frye Men's Scott Chelsea Harness Boots Created for Macy's
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      $228.00
      Now $113.93
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    • Extended Widths
      Rockport Men's Rugged Bucs H20 Waterproof Plain Toe Boots
      $120.00
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    • 3 colors
      Clarks Men's Original Desert Boots
      $130.00
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    • 2 colors
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      Florsheim Men's Duke Bike Toe Ankle Boot
      $135.00
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    • Timberland Men's Kendrick Chelsea Boots
      $140.00
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    • 2 colors
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      Florsheim Men's Essex Moc Toe Ankle Boot
      $130.00
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      (139)
    • Skechers Men's Workshire Boots from Finish Line
      $84.99
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      (103)
    • Unlisted by Kenneth Cole Men's Roll With It Boots
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      $75.00
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    • 2 colors
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      Clarks Men's Stinson Hi Top Wallabee Boots
      $110.00
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    • UGG® Men's Freamon Leather Chukka Boots
      $150.00
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    • Frye Men's Scott Suede Chukka Boots, Created for Macy's
      $228.00
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    • 2 colors
      Dr. Scholl's Men's Credence Suede Chelsea Boots
      $125.00
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    • Steve Madden Men's Verner Boots
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    • Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      $190.00
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      (153)
    • Mark Nason Los Angeles Men’s Double Cup - Sergeant Boots from Finish Line
      $150.00
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    • The North Face Men's Storm III Waterproof Mid-High Boots
      $120.00
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    • UGG® Men's Olivert Boots
      $190.00
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      (2)
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