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Ponytail Hats, Caps and Beanies

  • 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
    $ 29.99
    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 trimmed wit...

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    $ 29.99
  • Ginnie Cap in Microfiber Cap Great hats by Karen Keith
    Ginnie Cap in Microfiber Cap Great hats by Karen Keith GCMFpp Purple
    $ 16.50
    Great hats by Karen Keith

    Ginnie Cap in Microfiber

    Perfect for active and stylish ladies! Please note NO LOGO on front. Ginnie Cap with golf logo. Lightweight fashion cap for ponytail, braid or bun....

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    $ 16.50
  • Cotton Facesaver Cap - Milani Hats Cap Milani Hats
    Cotton Facesaver Cap - Milani Hats Cap Milani Hats BL7103sb Sky Blue Medium (57 cm)
    $ 12.50
    Milani Hats

    Cotton Facesaver Cap - Milani Hats

    Stay shaded and comfortable with this versatile cotton cap designed for all-day wear. The generous 4-inch peak shields your face and ears from the ...

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    $ 12.50
  • Gabi Ponytail Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Gabi Ponytail Fedora by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Gabi Ponytail Fedora by Wallaroo Hat Company

    The Gabi Ponytail Fedora is thoughtfully designed for women who want sun protection without sacrificing their favorite hairstyles. A discreet openi...

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    $ 61.00
  • Petite Gabi by Wallaroo Hat Company Safari Hat Wallaroo Hats
    Petite Gabi by Wallaroo Hat Company Safari Hat Wallaroo Hats
    $ 61.00
    Wallaroo Hats

    Petite Gabi by Wallaroo Hat Company

    The Petite Gabi Ponytail Fedora offers a smart, comfortable solution for women with smaller head sizes who prefer wearing their hair up. A discreet...

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    $ 61.00
  • Ginnie Cap in Rayon Mesh with Golf Logo Cap Great hats by Karen Keith
    Ginnie Cap in Rayon Mesh with Golf Logo Cap Great hats by Karen Keith GCME-Gnv Navy
    $ 16.50
    Great hats by Karen Keith

    Ginnie Cap in Rayon Mesh with Golf Logo

    Perfect for active and stylish ladies! Golf logo on front. Ginnie cap without logo Grey trim. Lightweight. Terrycloth sweatband. Adjustable velcro ...

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    $ 16.50
  • Ginnie Cap in Rayon Mesh Cap Great hats by Karen Keith GCME-BLK Black
    Ginnie Cap in Rayon Mesh Cap Great hats by Karen Keith
    $ 16.50
    Great hats by Karen Keith

    Ginnie Cap in Rayon Mesh

    Perfect for any sports and outdoor activity. Solid color caps with grey trim. Lightweight cap with open crown for bun, braid or ponytail. Terryclot...

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    $ 16.50
  • Ginnie Cap in Microfiber with Golf Logo Cap Great hats by Karen Keith
    Ginnie Cap in Microfiber with Golf Logo Cap Great hats by Karen Keith GCMF-Gbk Black
    $ 16.50
    Great hats by Karen Keith

    Ginnie Cap in Microfiber with Golf Logo

    Perfect for active and stylish ladies! Golf logo on front. Ginnie cap without embroidered logo. Lightweight cap with open back for ponytail or bun....

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    $ 16.50
  • Metallic Ponytail Facesaver Hat - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats hh1447C bn Brown-Gold M/L (57-59 cm)
    Metallic Ponytail Facesaver Hat - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats hh1447B tn Tan-Gold M/L (57-59 cm)
    $ 36.00
    Sun N Sand Hats

    Metallic Ponytail Facesaver Hat - Sun 'N' Sand Hats

    Facesaver style hat with brimless back. Metallic tweed detail creates a glitzy sparkle in the sun. Ponytail hole cut in back with elastic closure. ...

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    $ 36.00
  • 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
    $ 29.99
    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...

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    $ 29.99
  • 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
    $ 30.00
    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...

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    $ 30.00
  • Amazon Cotton Facesaver Cap with Mesh Side - Dorfman Hats Cap Dorfman Hat Co.
    Amazon Cotton Facesaver Cap with Mesh Side - Dorfman Hats Cap Dorfman Hat Co. L15 White
    $ 19.99
    Dorfman Hat Co.

    Amazon Cotton Facesaver Cap with Mesh Side - Dorfman Hats

    Lightweight cotton facesaver cap. Breezy mesh sidewall. Soft, stitched bill with 3.5" peak. Velcro® backstrap. Ponytail hole. 100% cotton.

    $ 19.99
  • Straw Brim Cap Hat with Sash - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2416C Black Tweed M/L (58 cm)
    Straw Brim Cap Hat with Sash - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats
    $ 37.50
    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...

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    $ 37.50
  • Wide Brim Straw Ponytail Facesaver Sun Hat - Boardwalk Hats Wide Brim Hat Boardwalk Style Hats
    Wide Brim Straw Ponytail Facesaver Sun Hat - Boardwalk Hats Wide Brim Hat Boardwalk Style Hats DA1929-IVO Ivory Tweed OS
    $ 27.00
    Boardwalk Style Hats

    Wide Brim Straw Ponytail Facesaver Sun Hat - Boardwalk Hats

    This Wide Brim Straw Ponytail Facesaver Sun Hat from Boardwalk Hats offers sun protection. Its UPF 50+ rating guarantees over 98% protection from h...

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    $ 27.00
  • Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats
    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats Wide Brim Sun Hat Scala Hats LT209-TOA Toast
    $ 36.99
    Scala Hats

    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats

    Woven Bangkok toyo straw butterfly brim sun hat. Large, 4.50" wide bound floppy brim split in back. Perfect for low ponytails. UPF 50+ sun protecti...

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    $ 36.99
  • 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

    Experience the ultimate in travel-friendly style with this innovative open crown visor. The shapeable wire-edged brim stretches a generous 5 inches...

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    $ 23.00
  • Women's Hiking Hat with Ponytail Hole - Scala Collection Trail Hat Scala Hats LC833-PINK Pink M/L (57-59 cm)
    Women's Hiking Hat with Ponytail Hole - Scala Collection Trail Hat Scala Hats LC833-LAV 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...

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    $ 32.99
  • 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...

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    $ 43.00
  • Ribbon and Straw Wide Brim Ponytail Sun Hat - Boardwalk Hats Visor Cap Boardwalk Style Hats
    Ribbon and Straw Wide Brim Ponytail Sun Hat - Boardwalk Hats Visor Cap Boardwalk Style Hats DA1930-IVBK Ivory / Black OS
    $ 25.00
    Boardwalk Style Hats

    Ribbon and Straw Wide Brim Ponytail Sun Hat - Boardwalk Hats

    This stylish Ribbon and Straw Wide Brim Ponytail Sun Hat from Boardwalk Hats offers 50+ UPF sun protection and a visor hat design with a 5" wide st...

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    $ 25.00
  • 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...

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    $ 24.00
  • Wide Brim Cap Hat with Side Bow - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2175B Toast Medium (57 cm)
    Wide Brim Cap Hat with Side Bow - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2175D Black Tweed Medium (57 cm)
    $ 31.00
    Sun N Sand Hats

    Wide Brim Cap Hat with Side Bow - Sun 'N' Sand Hats

    Facesaver style hat with brimless back. Brim cap hat with ponytail hole. Cute straw trimmed ribbon side bow with pineapple pin. Brim covers face an...

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    $ 31.00
  • 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 4.75" peak...

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    $ 31.00
  • 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...

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    $ 10.00
  • 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
  • Ponytail Straw Sun Hat with Adjustable Sizing - Sun 'N' Sand Hats Wide Brim Hat Sun N Sand Hats
    Ponytail Straw Sun Hat with Adjustable Sizing - Sun 'N' Sand Hats Wide Brim Hat Sun N Sand Hats HH2991B Black Tweed OS
    $ 37.50
    Sun N Sand Hats

    Ponytail Straw Sun Hat with Adjustable Sizing - Sun 'N' Sand Hats

    Cooling comfort and skin protection provided by this ponytail facesaver hat. Perfect to keep your hair off your shoulders and your face protected f...

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    $ 37.50
  • Cotton Sun Hat with Ponytail Opening - Scala Hats for Women Wide Brim Hat Scala Hats SCA11739-WHBLK White / Black M/L (57 - 58 cm)
    Cotton Sun Hat with Ponytail Opening - Scala Hats for Women Wide Brim Hat Scala Hats
    $ 37.00
    Scala Hats

    Cotton Sun Hat with Ponytail Opening - Scala Hats for Women

    Designed for active women who refuse to compromise on style or sun protection, this Scala cotton sun hat combines practical functionality with eleg...

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    $ 37.00

Ponytail hats, caps, and beanies are designed to solve a long-standing style problem: how to wear a hat comfortably when your hair is up. With a purpose-built opening in the back or top, these hats let you pull a ponytail or bun through naturally—so the crown sits correctly, the fit feels better, and you’ll never have to cram your hair under a hat again. This newer (and long-awaited) design is a game-changer for women who love wearing their hair up and want sun protection or warmth without distortion, bulk, or discomfort.

Ponytail Hat Styles You’ll Love

1) Straw Hats with Ponytail Opening

These styles often feature an opening at the back of the crown, with a hook-and-loop (Velcro®) closure that makes it easy to place your hair without pulling it through a tight hole. Crowns may be round or pinched (fedora-style), and both the opening and split brim are typically ribbon-bound for a finished look. Brim widths commonly range from 3" to 5", letting customers choose the coverage that fits their activity and sun needs.

Key benefits shoppers care about:

  • Breathable summer comfort: Natural straw, paper-braid, or poly-straw keeps airflow moving on hot days.

  • Sun protection + shade: Tightly woven/braided materials plus a wide brim help protect face, neck, and shoulders.

  • Larger, more flexible opening: Great for low ponytails, high ponytails, and messy buns—easy placement with the closure.

  • Adjustable sizing: Hook-and-loop closures typically provide about an inch of adjustability for a snug or relaxed fit.

  • The brimless back or split brim function: The “butterfly split” reduces brim bumping, making it easier for driving or lounging in a chair.

  • Travel-friendly: Many styles are packable, making them ideal for vacations and everyday carry.

2) Trail Hats with Ponytail Hole

Built for active outdoor wear, ponytail trail hats may have a full brim with a ponytail opening, or a neck-cape style with a slit for hair. These are commonly made with lightweight performance fabrics that keep you cooler and more comfortable while hiking, running, or spending long hours outside.

Why they convert:

  • Sporty performance + airflow: Quick-dry, ultra-light materials for active days.

  • Enhanced coverage: Wide brims and optional neck capes protect ears, neck, and shoulders.

  • Low maintenance: Often washable, fast-drying, and easy to pack flat or roll up.

3) Ponytail Yoga & Baseball Caps

Some caps include a ponytail opening, but true ponytail caps are designed to handle higher ponytails and buns, too. Openings may be triangular with straps, a slit (sometimes zippered), or a stretch opening.

Best-selling benefits:

  • Comfort + glare reduction: Great for everyday wear and sports.

  • Easy care: Many are washable or easy to spot clean.

  • Pool-friendly options: Some designs work especially well for swimming or humid conditions.

4) Ponytail Beanies

A cozy knit beanie—often acrylic or wool—with an opening at the top so hair can sit naturally without compromising warmth. Available in snug or slouchy fits, these are ideal for winter activities and cold-weather errands.

Why customers keep them:

  • Warmth without the “hat bump”: Keeps the head warm while letting hair up comfortably.

  • Style variety: Rib knit, cable knit, pom-poms, and even lined versions (fleece/sherpa/faux fur) for extra insulation.

  • Adjustable openings: Stretchy closures make it easy to pull hair through and tighten as needed.

Closing Brand Note

In a world where style matters as much as function, ponytail hats are a must-have. They keep hair off your neck, improve fit, and let you move through the day—errands, travel, trails, or slopes—looking polished and feeling comfortable.