Skip to content

Filters

Plus Size Hats for Big Heads - Extra-Large to 3XL Hat Sizes

  • Ponytail Summer Fedora Hat - Boardwalk Style Safari Hat Boardwalk Style Hats
    Ponytail Summer Fedora Hat - Boardwalk Style Safari Hat Boardwalk Style Hats DA1968-BKT Black Tweed M/L (58 cm)
    $ 24.00
    Boardwalk Style Hats

    Ponytail Summer Fedora Hat - Boardwalk Style

    Ponytail fedora hat with brimless back. Teardrop crown with slight front pinch. Front and side brim is 3" wide. Ponytail opening with hook and loop...

    View full details
    $ 24.00
  • Wide Bill Cap with Open Crown for Ponytail - Panama Jack Hats Cap Panama Jack Hats
    Wide Bill Cap with Open Crown for Ponytail - Panama Jack Hats Cap Panama Jack Hats PJL732-WHT White M/L
    $ 31.00
    Panama Jack Hats

    Wide Bill Cap with Open Crown for Ponytail - Panama Jack Hats

    Super lightweight microfiber fabric ponytail cap. Perfect for water aerobic, yoga, running or any sport. Floatable foam round brim, with 5" peak. T...

    View full details
    $ 31.00
  • Ponytail Hole Fedora for Large Heads - Karen Keith Hats Facesaver Hat Great hats by Karen Keith
    Ponytail Hole Fedora for Large Heads - Karen Keith Hats Facesaver Hat Great hats by Karen Keith BT14CB-B Black Tweed L/XL
    $ 29.00
    Great hats by Karen Keith

    Ponytail Hole Fedora for Large Heads - Karen Keith Hats

    Best selling ponytail hole hat now in large size. Dented and pinched low profile crown. Ponytail hole with Velcro© closure in back to adjust fit. R...

    View full details
    $ 29.00
  • Karen Keith Straw No Back Hat with Ponytail Hole Facesaver Hat Great hats by Karen Keith
    Karen Keith Straw No Back Hat with Ponytail Hole Facesaver Hat Great hats by Karen Keith BT9-CB-L Black One Size
    $ 27.99
    Great hats by Karen Keith

    Karen Keith Straw No Back Hat with Ponytail Hole

    Natural straw color backless facesaver hat with ponytail hole. Downward sloping 4" wide brim on front and sides, brimless back. Contrast color edge...

    View full details
    $ 27.99
  • Women's Hiking Hat with Ponytail Hole - Scala Collection Trail Hat Scala Hats LC833-ASST PK Pink M/L (57-59 cm)
    Women's Hiking Hat with Ponytail Hole - Scala Collection Trail Hat Scala Hats LC833-ASST LV Lavender M/L (57-59 cm)
    $ 32.99
    Scala Hats

    Women's Hiking Hat with Ponytail Hole - Scala Collection

    Dimensional brim hiking hat. Oval crown with mesh crown and mesh inner lining. Wide downward brim, 3.5" with black brim top. Underbrim matches colo...

    View full details
    $ 32.99
  • Open Crown Ponytail Roll Up Sun Visor Hat - Jeanne Simmons Hats Facesaver Hat Jeanne Simmons
    Open Crown Ponytail Roll Up Sun Visor Hat - Jeanne Simmons Hats Facesaver Hat Jeanne Simmons js6014nv Navy OS
    $ 23.00
    Jeanne Simmons

    Open Crown Ponytail Roll Up Sun Visor Hat - Jeanne Simmons Hats

    Solid color sewn ribbon hat with open crown top and back. Shapeable brim with wire edge, 5" wide. Velcro® closure over split brim in back. Horizont...

    View full details
    $ 23.00
  • Lucy Palm Leaf Sun Hat with Ponytail Hole - Tula Hats Wide Brim Hat Tula Hats TU1-1970 Burnt Palm M/L (57 - 58 cm)
    $ 43.00
    Tula Hats

    Lucy Palm Leaf Sun Hat with Ponytail Hole - Tula Hats

    Palm leaf sun hat for women.  Great ladies hat style to wear with ponytails or messy buns. Slightly downward sloping, 4" wide brim. Split in back f...

    View full details
    $ 43.00
  • Straw Brim Cap Hat with Sash - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats
    Straw Brim Cap Hat with Sash - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2416C Black Tweed M/L (58 cm)
    $ 31.00
    Sun N Sand Hats

    Straw Brim Cap Hat with Sash - Sun 'N' Sand Hats

    Facesaver style hat with brimless back. Multitone straw braid cap. Chiffon sash tied into long bow.  Brim has a 3.5" peak on front, disappears towa...

    View full details
    $ 31.00
  • Gabi Ponytail Hole Fedora - Wallaroo Hats Safari Hat Wallaroo Hats
    Gabi Ponytail Hole Fedora - Wallaroo Hats Safari Hat Wallaroo Hats GABI-IVO Ivory M/L (58 cm)
    $ 51.00
    Wallaroo Hats

    Gabi Ponytail Hole Fedora - Wallaroo Hats

    Backless Fedora Hat with Ponytail Hole. Disappearing brim, 3.25" on front and sides, brimless back. Ponytail opening with Velcro© closure in back t...

    View full details
    $ 51.00
  • Tweed Straw Facesaver Hat with Ponytail Hole - JSA Facesaver Hat Jeanne Simmons
    Tweed Straw Facesaver Hat with Ponytail Hole - JSA Facesaver Hat Jeanne Simmons js8218bk Black tweed
    $ 25.00
    Jeanne Simmons

    Tweed Straw Facesaver Hat with Ponytail Hole - JSA

    Multi-tone tweed braid backless beach hat with ponytail hole. Downward sloping 4" wide brim on front and sides, brimless back. Round opening in bac...

    View full details
    $ 25.00
  • Hand Crocheted Fashion Bun Beanie with Bow - DNMC Hats Beanie Boardwalk Style Hats
    Hand Crocheted Fashion Bun Beanie with Bow - DNMC Hats Beanie Boardwalk Style Hats da7016 Black M/L (58 cm)
    $ 12.50
    Boardwalk Style Hats

    Hand Crocheted Fashion Bun Beanie with Bow - DNMC Hats

    Hand crocheted fashion beanie hat. Opening on top for ponytail or messy bun. Bow accent. One size. Best fit 57-59 cm, medium to large. 100% acrylic

    $ 12.50
  • Cable Knit Messy Bun Beanie - DNMC Beanie Boardwalk Style Hats
    Cable Knit Messy Bun Beanie - DNMC Beanie Boardwalk Style Hats da7015 Navy M/L (58 cm)
    $ 10.00
    Boardwalk Style Hats

    Cable Knit Messy Bun Beanie - DNMC

    Cable knit beanie with opening on top for ponytail or bun. Keeps ears and head warm while providing room for your hair. One size. Best fit 57-59 cm...

    View full details
    $ 10.00
  • Metallic Ponytail Facesaver Hat - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats hh1447B tn Tan-Gold M/L (57-59 cm)
    Metallic Ponytail Facesaver Hat - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats hh1447C bn Brown-Gold M/L (57-59 cm)
    $ 27.00
    Sun N Sand Hats

    Metallic Ponytail Facesaver Hat - Sun 'N' Sand Hats

    Facesaver style hat with brimless back. Metallic tweed accent, gives a glitzy sparkle in sunshine. Ponytail hole cut in back with elastic closure. ...

    View full details
    $ 27.00
  • Karen Keith Tweed Straw Facesaver Hat with Ponytail Hole Facesaver Hat Great hats by Karen Keith BT9CB-C Black tweed
    Karen Keith Tweed Straw Facesaver Hat with Ponytail Hole Facesaver Hat Great hats by Karen Keith
    $ 27.99
    Great hats by Karen Keith

    Karen Keith Tweed Straw Facesaver Hat with Ponytail Hole

    Multi tone tweed braid facesaver style hat with ponytail hole. Downward sloping 4" wide brim on front and sides, brimless back. Brim is trim Pr...

    View full details
    $ 27.99

Comfortable and stylish large head hats

Let's face it, some of us need more room to think. Don't try to fit into the one size fits all hat, find a well fitting hat for big heads. Large and XL hat sizes for ladies and XXL to 3X-Large hat sizes for men. Large variety of plus size hat styles for men and women.