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Extended Sizes

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  1. Bailey of Hollywood Riff Fedora - Black
    Regular Price $150.00 Starting at $75.00
  2. Bailey of Hollywood Blixen LiteFelt® Fedora  - Black
    Regular Price $118.00 Starting at $59.00
  3. Jackman
    Regular Price $135.00 Starting at $87.75
  4. Salem Braided Fedora - Black/L
    Regular Price $85.00 Starting at $55.25
  5. Bailey - Black
    Regular Price $118.00 Starting at $59.00
  6. Bailey of Hollywood Tino LiteFelt® Fedora - Black
    Regular Price $105.00 Starting at $52.50

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Extra-Large Hats with a Dash of Confidence

The days of struggling with ill-fitting hats have ended thanks to our XXL hats and caps. Yearning for the cultured look of a Perry hat with a center dent? Or, seeking the distinguished look of the Dillinger with its grandiose profile? We carry these and more hats in large sizes. With top-quality materials ranging from wool to Litefelt, our hats are exceptionally durable and timelessly fashionable.

Take Your Style Up a Notch with Ease

Bailey Hats marries the irresistibility of cowboy toughness with modern elegance with our two collections. With our many statement pieces, you’ll instantly become a western style trailblazer, no matter where you are.

Like the rest of our collection, our extra-large hats stand out for their shape retention, premium feel, and water resistance. Invest in the unique combination of incredible functionality and style by ordering your favorite XXL caps today!

Stellar Customer Service Every Time

As a pioneer of the best western hats around, we take pride in covering your crown. Rugged cowboys and shining lights alike have praised us for our matchless products. However, we have also earned a reputation for second-to-none customer service. For instance, we offer free shipping in the contiguous US on all orders over $120. We also offer hassle-free shipping for returns in the US.

See the look you want today in our collection of XXL caps and hats, and order now!


  1. How should extra-large pork pie hats fit on your head?

Place this hat directly atop your head, making sure that it is level. Note that this hat is best suited for those with an oval-shaped or narrow face versus a square or round face.

  1. What material for XXL hats is best for staying cool during the summer months?

Choose a hat made with Bangora straw, like our Desert Breeze western-style hat. This type of hat is lightweight and features ample ventilation.

  1. What should a fedora for men be worn with?

A gentleman’s fedora, like the Brandt, is best paired with an overcoat, suit jacket, sport coat, or blazer.

  1. What sizes are considered XXL and XXXL?

For USA standard sizing, XXL is 7 ¾ and 7 ⅞, and XXXL is 8 and 8 ⅛. In inches, XXL is 24 ⅜” to 24 ⅞”, and XXXL is 25 ⅛” to 26 ½”. In centimeters, XXL is 62-63cm, and XXXL is 64-65cm.