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 Winter Shoes

Shopping for Men’s Winter Shoes? Find Formal Men’s Winter Shoes, Casual Men’s Winter Shoes and Slip-On Men’s Winter Shoes at Macy’s.

Men’s winter shoes have a big job to do. They need to protect the feet, keeping them dry and warm, and offer enough support to prevent injury. They need to be able to brave the weather without letting in water or becoming damaged, and look great with the rest of a winter wardrobe, too. Luckily, there is a variety of men’s winter shoes ranging from slip-on shoes to boots, making finding the perfect pair easy.

Need something stylish yet formal enough to wear to work? Chukka boots could be the perfect choice. With a high top, perfect for stopping rain from getting in, these boots come in a number of sleek designs that looks great with a suit or smart outfit. Opt for a Steve Madden design in a shiny black for a shoe that will go effortlessly with any smart outfit.

Looking for something heavy-duty? Dr Martens are the classic choice. Available in a range of styles and designs that appeal to different tastes, these boots are known for being tough and comfortable. Make them easy to coordinate by opting for a pair in easy colors, such as black and white. These will go well with jeans on casual days, waterproof trousers on adventurous days and smart outfits on formal days.

Want something eye-catching for adventuring in? Timberland boots are designed for the active lifestyle, combining comfort with plenty of grip and designs that specialize in everything from mountain climbing to yachting. The smooth black design has a contemporary feel, or go traditional with wheat boots. Lauren Ralph Lauren ranger boots are another great choice, featuring plenty of buckles and a fur lining that will keep your feet dry and warm whatever the weather. You could even opt for’s Levi boots, an effortless style and a men’s winter shoes classic.

Find the perfect men’s winter shoes for any occasion at Macy’s.

more
  • 108 items in Mens Winter Shoes

    • Filter
    • Sort By
    • All Items (108)
    • Free Pick Up
    • Sort by
    • 5 colors
      Extended Widths
      Clarks Men's Bushacre 2 Chukka Boots
      Limited-Time Special
      $100.00
      Sale $69.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (22)
    • 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 Maddsen Waterproof Hiking Boots
      Limited-Time Special
      $120.00
      Sale $99.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (322)
    • 2 colors
      Steve Madden Men's Jonnie Boots, Created for Macy's
      Limited-Time Special
      $110.00
      Sale $79.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (34)
    • 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)
    • 2 colors
      Florsheim Men's Beat Plain-Toe Chelsea Gore Boots
      Limited-Time Special
      $130.00
      Sale $77.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (48)
    • 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)
    • Extended Widths
      Clarks Men's Bushacre 2 Chukka Boot
      Limited-Time Special
      $100.00
      Sale $69.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (122)
    • 2 colors
      Stacy Adams Men's Alomar Cap-Toe Chelsea Boots
      Limited-Time Special
      $105.00
      Sale $72.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (39)
    • 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)
    • Extended Widths
      Kenneth Cole Reaction Desert Sun Leather Chukka Boots
      Limited-Time Special
      $98.00
      Sale $48.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (62)
    • 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)
    • Clarks Men's Hinman Mid-High Boots
      Limited-Time Special
      $100.00
      Sale $69.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (4)
    • 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)
    • G. H. Bass & Co. Men's Bennett Chukka Boots
      Limited-Time Special
      $110.00
      Sale $81.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • 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)
    • Calvin Klein Men's Bain Saffiano Chukka Boots
      Limited-Time Special
      $115.00
      Sale $68.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (3)
    • 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)
    • 2 colors
      Extended Widths
      Clarks Men's Stinson Hi Top Wallabee Boots
      $110.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (35)
    • Frye Men's Scott Chelsea Harness Boots Created for Macy's
      LAST ACT
      $228.00
      Now $113.93
      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
      (2)
    • Florsheim Men's Streets Wingtip Chelsea Gore Boots
      $130.00
      Now $84.50
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $67.60
      New markdown
      Prices just reduced - Limited Quantities
      New markdown
      (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)
    • Unlisted by Kenneth Cole Men's Roll With It Boots
      LAST ACT
      $75.00
      Now $37.43
      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
      (53)
    • 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)
    • 2 colors
      Tommy Hilfiger Men's Casey Waterproof Duck Boots Created for Macy's
      Limited-Time Special
      $90.00
      Sale $44.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (73)
    • 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