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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
    $ 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 trimmed wit...

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    $ 27.99
  • 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

    100% Cotton classic wide bill cap. Round bill with 4" peak provides good sun protection for ears too. Six panel dome crown with button top. Elastic...

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    $ 12.50
  • 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...

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    $ 51.00
  • Petite Gabi Ponytail Hole Fedora for Small Heads - Wallaroo Hats Safari Hat Wallaroo Hats
    Petite Gabi Ponytail Hole Fedora for Small Heads - Wallaroo Hats Safari Hat Wallaroo Hats PGABI-BG Beige Small (55-56 cm)
    $ 52.00
    Wallaroo Hats

    Petite Gabi Ponytail Hole Fedora for Small Heads - Wallaroo Hats

    Backless Fedora Hat with Ponytail Hole for Petites. Tapering brim, 3" wide on from and sides, brimless back.  Velcro© closure in back to adjust fit...

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    $ 52.00
  • 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. ...

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    $ 27.00
  • 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...

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    $ 31.00
  • 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...

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    $ 27.99
  • Poly-Cotton Fashion Cap with Metallic Lurex - Sun 'N' Sand Hats Cap Sun N Sand Hats HH2187E Blue S/M (56-57 cm)
    Poly-Cotton Fashion Cap with Metallic Lurex - Sun 'N' Sand Hats Cap Sun N Sand Hats HH2187D Black S/M (56-57 cm)
    $ 31.00
    Sun N Sand Hats

    Poly-Cotton Fashion Cap with Metallic Lurex - Sun 'N' Sand Hats

    Metallic thread accent summer cap with ponytail hole. Wide brim with 3.5" peak. Teeny-tiny bead band accent. Ribbon inner band. Elastic closure w...

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    $ 31.00
  • 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 LT209tt Toast
    $ 31.99
    Scala Hats

    Bangkok Toyo Split Brim Summer Floppy Hat - Scala Hats

    Woven toyo straw capeline style hat with butterfly brim. Large, 4.50" wide bound floppy brim split in back. Perfect for ponytails. UPF 50+ sun prot...

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    $ 31.99
  • 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
  • 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
  • Large Bill Trail Hat with Sun Shade and Floatable Brim - Scala Hats Trail Hat Scala Hats
    Large Bill Trail Hat with Sun Shade and Floatable Brim - Scala Hats Trail Hat Scala Hats LC829-IVORY Ivory S/M
    $ 31.99
    Scala Hats

    Large Bill Trail Hat with Sun Shade and Floatable Brim - Scala Hats

    Functional and stylish women's sun shade trail hat. Wide 180 degrees round bill protects face and ears, 4.5". Neck cape is 5" long to cover back of...

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    $ 31.99
  • 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...

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    $ 25.00
  • Wide Brim Cap Hat with Side Bow - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2175D Black Tweed Medium (57 cm)
    Wide Brim Cap Hat with Side Bow - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2175B Toast 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
  • Ponytail Hole Knit Slouchy Beanie - Karen Keith Beanie Great hats by Karen Keith
    Ponytail Hole Knit Slouchy Beanie - Karen Keith Beanie Great hats by Karen Keith bean1tn Tan
    $ 12.00
    Great hats by Karen Keith

    Ponytail Hole Knit Slouchy Beanie - Karen Keith

    Knit messy bun beanie cap with elastic ponytail hole. Cuffed beanie hat. Karen Keith leatherette patch. One size. 100% acrylic

    $ 12.00
  • Backless Ponytail Opening Fedora - Sun 'N' Sand Hats Safari Hat Sun N Sand Hats HH2943A Natural Tweed M/L (58 cm)
    Backless Ponytail Opening Fedora - Sun 'N' Sand Hats Safari Hat Sun N Sand Hats HH2943B Black Tweed M/L (58 cm)
    Sold out
    $ 33.50
    Sun N Sand Hats

    Backless Ponytail Opening Fedora - Sun 'N' Sand Hats

    Ponytail sun hat for women. Fedora-like dented and pinched crown, 3.5" deep. Disappearing ribbon bound brim, 3" wide on front and sides, no brim ba...

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    $ 33.50
  • Vented Straw Brim Cap with Ribbon Bound Bill - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2704B Tan OS (57 cm)
    Vented Straw Brim Cap with Ribbon Bound Bill - Sun 'N' Sand Hats Facesaver Hat Sun N Sand Hats HH2704A White OS (57 cm)
    $ 28.00
    Sun N Sand Hats

    Vented Straw Brim Cap with Ribbon Bound Bill - Sun 'N' Sand Hats

    Unique vented crown straw cap. Ribbon trimmed bill, 3.5" peak. Braid band with ribbon trim and latch accent. Inner drawstring to adjust fit. UPF 50...

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    $ 28.00
  • 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-BLK 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
  • Ruched Ponytail Slouchy Beanie - Angela & William Beanie Epoch Hats BN1999dg Dark Grey
    Ruched Ponytail Slouchy Beanie - Angela & William Beanie Epoch Hats BN1999nv Navy
    $ 13.25
    Epoch Hats

    Ruched Ponytail Slouchy Beanie - Angela & William

    Ruched knit beanie hat. Slouchy beanie with opening for ponytail or messy bun. Double knit layer provides extra warmth. Angela & William hats l...

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    $ 13.25
  • 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

PONYTAIL HATS, CAPS, BEANIES

Ponytail hats are designed to accommodate your ponytail or bun. Ponytail hats have a unique opening in the back or top of the hat to allow you to pull your hair through. This hat style solved the incompatibility problem of hats and ponytails. In the realm of hat history, this style is a new design, but long awaited by women who prefer their hair up, and have given up wearing a hat because hats do not look right with the lump of the hair misshaping the crown, or the bun preventing the hat to sit on the top of the head. You will never again have to tuck your hair into your hat. Now, let’s explore available ponytail hat styles and brands.

Ponytail Hat Styles:

1. Straw Hats with Ponytail Opening

The back of the crown of these straw hats has an opening, and the brim is split. Hook and loop strap closure allow you to pull your hair through easily, and adjust the fit as needed. This style of a ponytail hat fits a wider range of sizes. The shape of the crown can be round or pinched, like a fedora. The ponytail opening and the brim are ribbon bound. The varying width of the brim, ranges from 3" to 5", allows you to choose a style to accommodate your activity and sun protection need. 

Advantages of Straw Ponytail Hats:

Breathability: Made of natural straws, modern paper-braid, or poly-straw. These hats are lightweight and breathable, allowing air to circulate and keep your head cool on sizzling summer days. Lucy Palm Leaf Sun Hat with Ponytail Hole is a natural straw hat made by the famous palm straw hat brand Tula Hats. Our best selling Karen Keith Tweed Straw Facesaver hat with Ponytail is made of paper-braid straw. Gabi Ponytail Hole Fedora by Wallaroo is made of Flexy-Weave® a poly-straw. 

Sun Protection: The material of these hats is tested for their UV blocking properties. Tightly woven or braided straw hats provide excellent sun protection. In addition, the wide brim provides ample shade to protect your face, neck, and shoulders from the sun’s harmful rays, helping to prevent sunburn and skin damage.

Larger Ponytail Opening: The opening of a straw hat is wide with varying height to accommodate low to high ponytails and buns comfortably. The hook and loop closure allows to easily place the hair without having to pull it through the ponytail hole. Boardwalk Hat’s Wide Brim Straw Ponytail Facesaver Sun Hat offers a high opening for a messy bun and a stylish straw bow detail over the Velcro® closure.

Adjustable Sizing: The hook and loop strap allows about an inch of adjustment on the OSFM hats accommodating a range of fit, and allows you reduce or expand the size and adjust from a snug to a looser fit. Some brands also offer small or large size ponytail hats. Karen Keith Ponytail Fedora Hat is made for larger head sizes, while Petite Gabi Fedora by Wallaroo Hat Company fits smaller head sizes.

Split Brim: The unique butterfly split prevents the wide brim from bumping into your back and pushing the hat forward, even the larger brim ponytail hats. This makes ponytail hats easy to wear when getting in and out of a car, or just lounging in a beach chair.

Functionality: Wide selection of styles to choose from to suit every taste and occasion. Whether you are at a summer barbeque or traveling around the world, ponytail hats will keep your hair off your face and off your neck ensuring you will be comfortable and fashionable. Packable ponytail hats make a great travel companion. Wallaroo’s Gabi ponytail hat pack easily and available in petite as well as OSFM to accommodate ladies with smaller head sizes.

2. Trail Hats with Ponytail Hole

Full brim trail hats feature ponytail openings like straw hats, while hats with a neck cape have a slit on the crown. Ponytail trail hats are made of lightweight materials ideal for any outdoor activities, as they provide sun protection and keep you cool and keep your hair off your neck.

Advantages of Ponytail Trail Hats:

Sporty style: Trail hats were designed for active lifestyles. Made of super lightweight performance fabrics, or quick-dry nylon for cooling all day comfort keeping your hair out of the way while you are hiking, running, or playing sports. Available in a variety of colors to match your outfit.

Sun Protection: UV blocking fabric and the wide brim protects your eyes, face, ears, neck, and shoulders from sun exposure. Trail hats with neck capes, such as the Large Bill Trail Hat with Sun Shade and Floatable Brim made by Scala Hats, were especially designed for neck and shoulder protection. Its wide brim also provides ample shade for your face.

Easy to Clean and Pack: Most nylon hats are washable, dry quickly, prevent stains and odor. These hats can be folded or packed flat, making them a convenient accessory to have whether you are going on vacation, or just have them in your bag for when you need it.

3. Ponytail Yoga and Baseball Caps

Unfitted baseball caps have opening for a ponytail, but the real ponytail caps will accommodate a high ponytail or bun as well. It can be a triangle shape with sectioning straps, a slit sometimes with a zipper closure, or a stretchy opening on top of the hat. Ginnie Caps™ have an open back with a smooth hook and loop closure that will not pull your hair. The open crown is perfect to show off your braided hair.

Advantages of Ponytail Caps:

Comfortable fit: When you just need to shade your eyes to reduce glare, baseball caps are a convenient choice as they are comfortable to wear. Ponytail caps are made of lightweight polyester, nylon, cotton, or Lycra®. Swimsuit Fabric Ponytail Baseball Cap by DPC Hats is perfect for the swimming pool with its crown top ponytail hole your hair is kept out of the water.

Convenience: Easy to pack, easy to clean. Most ponytail baseball caps are washable, or easy to spot clean, making them a low maintenance practical accessory to have wherever you are heading.

4. Ponytail Beanie Hat

A knit beanie made of acrylic or wool with an opening on top. Various lengths to choose from snug fitting to slouchy styles. Functional style to keep your head warm while allowing you to wear your ponytail or bun comfortably. Ideal for outdoor activities like skiing, snowboarding, or hiking.

Advantages of Ponytail Beanies:

Functionality: The primary function of a ponytail beanie is to keep your head warm and wear your hair comfortably. When you are out braving the elements, these beanies provide style and practicality. The clever ponytail opening is reinforced with a stretchy adjustable closure to easily pull your hair through, then tighten to your liking.

Style: Ponytail beanies come in various materials to suit your preferences and weather conditions. Common materials include soft acrylic yarn for warmth and comfort, wool for added insulation, or a blend of materials for durability and breathability. For extreme wintry weather, choose a ponytail beanie lined with warm fleece, sherpa, or faux fur. Choose from classic ribbed knit for a timeless look, cable knit for texture and visual interest, or pom-pom beanies for a playful whimsical look.

In our era fashion and style are as important as comfort and functionality. Ponytail hats are stylish and practical additions to your winter or summer wardrobe. Put your hair up and be ready to run errands, enjoy a stroll, or hit the slope.