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
  • 62 items in Comfort Most Comfortable Shoes

    • Filter
    • Sort By
    • All Items (62)
    • 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)
    • 3 colors
      Cole Haan Men's Original Grand Wing Oxfords
      $150.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (35)
    • 2 colors
      Lightweight
      Rockport Men’s Style Leader 2 Bike Toe Slip On Loafers
      Limited-Time Special
      $110.00
      Sale $76.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (84)
    • Extended Widths
      Rockport Men's Waterproof Northfield Oxford
      Limited-Time Special
      $110.00
      Sale $76.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (526)
    • 3 colors
      Cole Haan Men's Pinch Weekender Slip-Ons
      Limited-Time Special
      $90.00
      Sale $79.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (7)
    • 2 colors
      Extended Widths
      Rockport Men's Langdon Slip-On Sneakers
      Limited-Time Special
      $110.00
      Sale $76.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • 2 colors
      Tommy Hilfiger Men's Garson Oxfords
      Limited-Time Special
      $80.00
      Sale $47.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (9)
    • 2 colors
      Cole Haan Men's Grand Horizon Oxfords
      $250.00
      Now $162.50
      Extra 20% off use: SHOP
      Extra 20% off select merchandise!
      Extra 20% off use: SHOP
      With offer $130.00
      New markdown
      Prices just reduced - Limited Quantities
      New markdown
      (2)
    • 2 colors
      Kenneth Cole Reaction Men's Lyon Perforated Drivers
      Limited-Time Special
      $98.00
      Sale $57.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 2 colors
      Rockport Men's Aiden Penny Loafers
      Limited-Time Special
      $125.00
      Sale $86.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 3 colors
      Alfani Men's Varick Comfort FLX Textured Knit Oxfords, Created for Macy's
      Limited-Time Special
      $89.99
      Sale $44.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 3 colors
      Extended Widths
      Rockport Men's Get Your Kicks Mudguard Blucher Casual Shoes
      Limited-Time Special
      $110.00 - 120.00
      Sale $65.99 - 71.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (22)
    • 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
      Kenneth Cole Reaction Men's Vinny Bit Drivers
      Limited-Time Special
      $98.00
      Sale $57.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • 2 colors
      Weatherproof Vintage Men's Phoenix Sandals
      Limited-Time Special
      $50.00
      Sale $29.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (8)
    • 4 colors
      Crocs Men's Classic Clogs
      $35.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (5194)
    • 3 colors
      Frye Men's Harris Venetian Leather Loafers, Created for Macy's
      Limited-Time Special
      $158.00
      Sale $109.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 3 colors
      Johnston & Murphy Men's Walden Blucher Lace-Up Oxfords
      $129.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • 2 colors
      Stacy Adams Men's Northpoint Moc Toe Slip-On Loafers
      Limited-Time Special
      $60.00
      Sale $35.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (16)
    • 3 colors
      Cole Haan Men's Grand Pro Deck Leather Sneakers
      $130.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • Cole Haan Men's Pinch Weekender Embossed Weave Slip-Ons
      Limited-Time Special
      $100.00
      Sale $79.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 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)
    • 2 colors
      Hugo Boss Men's Traveling Dandy Suede Moccasins
      $205.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (1)
    • Stacy Adams Men's Dandy Suede Plain-Toe Oxfords
      Limited-Time Special
      $105.00
      Sale $62.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (5)
    • Timberland Men's Naples Trail Oxfords
      Limited-Time Special
      $120.00
      Sale $99.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (19)
    • 4 colors
      Dockers Men's Parkway 360 Shoes
      Limited-Time Special
      $80.00
      Sale $59.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • Cole Haan Men's Original Grand Plain-Toe Canvas Oxfords
      $150.00
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
      (2)
    • 2 colors
      Dockers Men's Parkway Leather Oxfords
      Limited-Time Special
      $90.00
      Sale $66.99
      Free ship at $49
      Enjoy Free Shipping at $49! See exclusions.
      Free ship at $49
    • 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)
    • 2 colors