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Men's Hats

  • Double Diamond Bangora Straw Gambler Hat - Biltmore Vintage Hats Gambler Hat Biltmore Hats
    Double Diamond Bangora Straw Gambler Hat - Biltmore Vintage Hats Gambler Hat Biltmore Hats BF129-IVORY2 Ivory Medium  (57 cm)
    $ 89.00
    Biltmore Hats

    Double Diamond Bangora Straw Gambler Hat - Biltmore Vintage Hats

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

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    $ 89.00
  • Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR73 Khaki L (59 cm)
    Woven Raffia Gambler Hat with Pineapple Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR73 Khaki M (57 cm)
    $ 44.99
    Scala Hats

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

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

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    $ 44.99
  • Khaki Cotton Tiller with Chin Cord - Legendary Stetson Hats Gambler Hat Stetson Hats
    Khaki Cotton Tiller with Chin Cord - Legendary Stetson Hats Gambler Hat Stetson Hats STC403-KAKI2 Khaki Medium (57 cm)
    $ 43.50
    Stetson Hats

    Khaki Cotton Tiller with Chin Cord - Legendary Stetson Hats

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

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    $ 43.50
  • Twisted Seagrass Golf Hat - Scala Hats Gambler Hat Scala Hats
    Twisted Seagrass Golf Hat - Scala Hats Gambler Hat Scala Hats MS299OS-SM Natural S/M ( 56 - 57 cm)
    $ 44.99
    Scala Hats

    Twisted Seagrass Golf Hat - Scala Hats

    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...

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    $ 44.99
  • Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats
    Burnt Palm Leaf Outback Sun Hat for Small Heads - Tula Hats Gambler Hat Tula Hats TU-15000S Burnt Palm Small (55-56 cm)
    $ 43.00
    Tula Hats

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

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

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    $ 43.00
  • Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR96-BLK1 Black S/M (21 1/2"-22 1/8")
    Marco Woven Raffia Gambler Hat with Turtle Tape Band - Scala Hats for Men Gambler Hat Scala Hats MR96-NAT1 Khaki S/M (21 1/2"-22 1/8")
    $ 44.99
    Scala Hats

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

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

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    $ 44.99
  • Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats Gambler Hat Stacy Adams Hats
    Jackson Wool Felt Porkpie Hat, up to 2XL - Stacy Adams Hats Gambler Hat Stacy Adams Hats SAW509 Black Large (23")
    Save 30%
    Original Price $ 64.25
    Current Price $ 44.95
    Stacy Adams Hats

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

    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...

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    Original Price $ 64.25
    Current Price $ 44.95
    Save 30%
  • Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats Gambler Hat Tula Hats
    Outback Burnt Palm Leaf Sun Hat up to 2XL - Tula Hats Gambler Hat Tula Hats TU5900 Burnt Palm XXL (62 cm)
    $ 45.00
    Tula Hats

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

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

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    $ 45.00
  • Braid Gambler Hat with 3-Pleat Cotton Band - Tommy Bahama Gambler Hat Tommy Bahama Hats
    Braid Gambler Hat with 3-Pleat Cotton Band - Tommy Bahama Gambler Hat Tommy Bahama Hats TBW265sm Natural S/M (56 - 57 cm)
    Sold out
    $ 39.00
    Tommy Bahama Hats

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

    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...

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    $ 39.00
  • Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats Gambler Hat Tula Hats
    Gambler Burnt Palm Leaf Sun Hat with Lattice Crown upto 2XL- Tula Hats Gambler Hat Tula Hats TU1-6000 Burnt Palm Small (55 - 56 cm)
    $ 45.00
    Tula Hats

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

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

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    $ 45.00
  • Trendsetter Shantung Porkpie - Biltmore Hats Gambler Hat Biltmore Hats
    Trendsetter Shantung Porkpie - Biltmore Hats Gambler Hat Biltmore Hats bs3npgtrenM Ivory Medium ((22-22 3/8")
    $ 77.00
    Biltmore Hats

    Trendsetter Shantung Porkpie - Biltmore Hats

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

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    $ 77.00
  • Raffia Gambler with Braided Jute Band by Kenny Keith Gambler Hat Great hats by Karen Keith rm20cm Natural M
    $ 29.00
    Great hats by Karen Keith

    Raffia Gambler with Braided Jute Band by Kenny Keith

    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. ...

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    $ 29.00

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.