Skip to content

Filters

Men's Hats

Contemporary and classic men's hat styles to fit your personality and need. From casual caps, bucket hats to dressy fedoras, gamblers and elegant derby hats, top hats. Sun protective summer hats, and winter hat styles.  

  • Double Diamond Bangora Straw Gambler Hat - Biltmore Vintage Hats, Gambler Hat - SetarTrading Hats
    Double Diamond Bangora Straw Gambler Hat - Biltmore Vintage Hats, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Double Diamond Bangora Straw Gambler Hat - Biltmore Vintage Hats

    $ 89.00

    Waxed bangora straw wide brim gambler hat by Biltmore Vintage Couture. Vertically woven two tone hat with double diamond shape crown top. Open weav...

    View full details
    $ 89.00
  • Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men

    $ 39.00

    Woven raffia gambler hat. Slightly tapered crown, telescope crown top. Pineapple and palm tree tape band with loop detail. Palm tree pin. Curled ed...

    View full details
    $ 39.00
  • Khaki Cotton Tiller with Chin Cord - Legendary Stetson Hats, Gambler Hat - SetarTrading Hats
    Khaki Cotton Tiller with Chin Cord - Legendary Stetson Hats, Gambler Hat - SetarTrading Hats
    Stetson Hats

    Khaki Cotton Tiller with Chin Cord - Legendary Stetson Hats

    $ 43.50

    Structured, water repellent cotton blend hat. Shapeable, stitched and bound brim, 3" wide. Triple Stetson metal eyelets on both side for airflow. W...

    View full details
    $ 43.50
  • Twisted Seagrass Golf Hat - Scala Hats, Gambler Hat - SetarTrading Hats
    Scala Hats

    Twisted Seagrass Golf Hat - Scala Hats

    $ 39.00

    Gambler style hat made for golf. Twisted seagrass hat. Flat crown with covered crown tip and airy sidewall. Front to back curved brim, 3" wide brim...

    View full details
    $ 39.00
  • Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats, Gambler Hat - SetarTrading Hats
    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats, Gambler Hat - SetarTrading Hats
    Tula Hats

    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats

    $ 43.00

    Great unisex outback gambler sun protection hat for small head sizes. Flat crown wall and telescope crown top. Provides excellent sun protection, U...

    View full details
    $ 43.00
  • Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men

    $ 39.00

    Woven raffia gambler hat. Turtle tape band with loop detail. 3" wide  brim with curled edge. Wide moisture wicking elasticized SCALA comfort sweatb...

    View full details
    $ 39.00
  • Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats, Gambler Hat - SetarTrading Hats
    Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats, Gambler Hat - SetarTrading Hats
    Stacy Adams Hats

    Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats

    $ 64.25

    Wool felt porkpie rocker hat with feather detail. Bound 2" wide brim. 16-Ligne grosgrain ribbon band with side bow. Leather inner band. Satin linin...

    View full details
    $ 64.25
  • Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats, Gambler Hat - SetarTrading Hats
    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats, Gambler Hat - SetarTrading Hats
    Tula Hats

    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats

    $ 45.00

    Great unisex outback gambler sun protection hat. Flat crown wall and telescope crown top. Provides excellent sun protection, UPF 50+. Flat brim wit...

    View full details
    $ 45.00
  • Braid Gambler Hat with 3-Pleat Cotton Band - Tommy Bahama, Gambler Hat - SetarTrading Hats
    Braid Gambler Hat with 3-Pleat Cotton Band - Tommy Bahama, Gambler Hat - SetarTrading Hats
    Tommy Bahama Hats

    Braid Gambler Hat with 3-Pleat Cotton Band - Tommy Bahama

    $ 39.00

    Tommy Bahama gambler golf hats. Elegant sun protection hat for men. Sunken crown. Flat brim, 3.25" wide. Wide 3-pleat cotton band with signature To...

    View full details
    $ 39.00
  • Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats, Gambler Hat - SetarTrading Hats
    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats, Gambler Hat - SetarTrading Hats
    Tula Hats

    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats

    $ 45.00

    Outback lattice is a gambler style sun protection hat with vented crown. Flat crown wall and telescope crown top. Provides excellent sun protection...

    View full details
    $ 45.00
  • Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams, Fedora Hat - SetarTrading Hats
    Save 39%
    Stacy Adams Hats

    Shiny Polybraid Porkpie Fedora Hat - Stacy Adams

    Original Price $ 25.00
    Current Price $ 15.20

    Soft polybraid pinched crown fedora. Small, shapeable brim, 1.75" wide. Faux leather band with tie print overlay. Loop with Stacy Adams pin. Faux l...

    View full details
    Original Price $ 25.00
    Current Price $ 15.20
    Save 39%
  • Trendsetter Shantung Porkpie - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Trendsetter Shantung Porkpie - Biltmore Hats, Gambler Hat - SetarTrading Hats
    Biltmore Hats

    Trendsetter Shantung Porkpie - Biltmore Hats

    $ 77.00

    Genuine handmade shantung porkpie style hat. Open weave mid-crown design. Soft, pliable, featherweight hat. 2 3/4" brim. Grosgrain ribbon band with...

    View full details
    $ 77.00
  • Pro Golf Woven Palm Gambler - Scala Hats for Men, Gambler Hat - SetarTrading Hats
    Scala Hats

    Pro Golf Woven Palm Gambler - Scala Hats for Men

    $ 59.99

    Natural straw color gambler style hat. Leather band with golf ornament. Turned up, 3" wide brim. Sunken crown top. Elastic CoolMax® comfort inner b...

    View full details
    $ 59.99
  • Raffia Gambler with Braided Jute Band by Kenny Keith, Gambler Hat - SetarTrading Hats
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    $ 29.00

    Soft braided raffia gambler style golf hat for men. Jute band with loop. Ribbon bound, 3.5" wide curled brim. Wide elasticized comfort inner band. ...

    View full details
    $ 29.00