Free Shipping with $49 purchase + Free Store Pickup. Contiguous US. Exclusions
Macy's Presents: The Edit- A curated mix of fashion and inspiration Check It Out
ADS FROM UNAFFILIATED SITES

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.

more
  • 35 items in Mens Leather Boots

    • Filter
    • Sort By
    • All Items (35)
    • Free Pick Up
    • Sort by
    • 2 colors
      Extended Widths
      Steve Madden Harken Chukka Boots
      Limited-Time Special
      $90.00
      Sale $69.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (177)
    • 2 colors
      Extended Widths
      Timberland Men's 6" Premium Waterproof Boot
      Everyday Value
      $189.98
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (508)
    • 2 colors
      Extended Widths
      Timberland Men's 6" Boot, Created for Macy's
      LAST ACT select colors
      $190.00
      Now $94.93 - 190.00
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded select colors
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (153)
    • Timberland Men's 6" Premium Fabric Boots
      LAST ACT
      $150.00
      Now $74.93
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • Extended Widths
      Timberland Men's 6" Basic Waterproof Boot
      Limited-Time Special
      $145.00
      Sale $109.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (345)
    • 3 colors
      Johnston & Murphy Copeland Chukka Boots
      $159.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (30)
    • Timberland Men's Kendrick Chukka Lace-Up Boots
      $140.00
      Now $91.00
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $72.80
      New markdown
      Prices just reduced - Limited Quantities
      New markdown
      (17)
    • Extended Widths
      Timberland Men's Earthkeeper Original 6" Boot
      Everyday Value
      $149.98
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (387)
    • Extended Widths
      Rockport Men's Classic Break Chukka Boot
      Limited-Time Special
      $135.00
      Sale $80.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (32)
    • HUGO Men's Dress Appeal Zip Boots
      $295.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • UGG® Men's Hannen TL Boots
      LAST ACT
      $230.00
      Now $114.93
      coupon excluded
      Last Act: Extra savings do not apply
      coupon excluded
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (234)
    • 2 colors
      Extended Widths
      Florsheim Men's Duke Bike Toe Ankle Boot
      $135.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (290)
    • 3 colors
      Extended Widths
      Stacy Adams Men's Madison Boot
      $135.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (164)
    • 5 colors
      Extended Widths
      Eastland Men's Lumber Up Boot
      Limited-Time Special
      $125.00 - 130.00
      Sale $111.99 - 116.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (14)
    • Extended Widths
      Rockport Men's Rugged Bucs H20 Waterproof Plain Toe Boots
      $120.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (84)
    • Timberland Men's Kendrick Chelsea Boots
      $140.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (14)
    • 2 colors
      Extended Widths
      Florsheim Men's Essex Moc Toe Ankle Boot
      $130.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (137)
    • 3 colors
      Clarks Men's Original Desert Boots
      $130.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (202)
    • ALDO Men's Sthephanus Double-Zip Boots
      $160.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • Eastland Men's Chester Boots
      Limited-Time Special
      $130.00
      Sale $116.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • Calvin Klein Men's Albe Nappa Leather Chukka Boots
      Limited-Time Special
      $150.00
      Sale $89.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 9 colors
      Extended Widths
      Eastland Men's Seneca Boot
      Limited-Time Special
      $110.00
      Sale $81.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (6)
    • Timberland Men's New Market Scuff Proof II 6'' Waterproof Boots
      $190.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (65)
    • 2 colors
      Eastland High Fidelity Lace-Up Boots
      Limited-Time Special
      $125.00
      Sale $111.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • Stacy Adams Men's Delaney Chukka Boots
      Limited-Time Special
      $105.00
      Sale $62.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (14)
    • 2 colors
      Carlos by Carlos Santana Men's Corazon Chukka Boots
      $159.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 2 colors
      Eastland Daily Double Side-Gore Boots
      Limited-Time Special
      $110.00 - 115.00
      Sale $98.99 - 102.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (3)
    • 2 colors
      UGG® Men's Freamon Leather Chukka Boots
      $150.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (22)
    • UGG® Men's Neumel Chukka Boots
      $140.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (15)
    • UGG® Men's Yucca Waterproof Boots
      $120.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (48)
    • Extended Widths
      Rockport Men's Essential Details Waterproof Chukka Boot
      $120.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (48)
    • 2 colors
      Eastland Men's Sherman 1955 Boots
      $225.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)