12 Days of Gifting: 25% Off Select Winter Styles*

Extended Sizes

Items 1-36 of 60

Page
per page
Set Descending Direction
  1. Bailey - Ash
    Salem
    Regular Price $85.00 Starting at $42.50
  2. Stedman
    Stedman
    Regular Price $210.00 Starting at $71.75
  3. Bailey Tino - Unbleached
    Tino
    Regular Price $135.00 Starting at $47.25
  4. Bailey -  Lazuli Blue
    Riff
    Regular Price $165.00 Starting at $82.50
  5. Bailey - Flint Gray
    Darron
    Regular Price $135.00 Starting at $67.50
  6. Bailey - Italian Clay
    Derby
    Regular Price $160.00 Starting at $80.00
  7. Jackman
    Jackman
    Regular Price $135.00 Starting at $67.50
  8. USA Desert Breeze
    USA Desert Breeze
    Starting at $60.00
  9. Bailey - Beige Stripe
    Leif
    Starting at $90.00
  10. Elephant Grey Swirl F24
    Criss
    Starting at $175.00
  11. Bailey Deepwoods Camo
    Opsec
    Starting at $145.00
  12. Bailey - Espresso Check
    Hernen
    Starting at $225.00
  13. Bailey - Camel
    Redline
    Starting at $112.00
  14. Bailey Pennswoods Camo
    EDC
    Starting at $100.00
  15. Ganey
    Ganey
    Starting at $75.00
  16. Bailey - Java Bean
    Stedman
    Starting at $210.00
  17. Codner
    Codner
    Regular Price $130.00 Starting at $45.50
  18. Main Image
    Desert Knight
    Starting at $60.00
  19. Main Image
    Seneca 15X
    Starting at $100.00
  20. Main Image
    Farson 7X
    Regular Price $80.00 Starting at $40.00
  21. Zippo 2X
    Zippo 2X
    Starting at $130.00
  22. Hastings 4X
    Hastings 4X
    Starting at $180.00
  23. Bailey of Hollywood Salter Panama Fedora - Natural
    Salter
    Starting at $375.00
  24. Wheeler 3X
    Wheeler 3X
    Starting at $140.00
  25. Bailey - Unbleached
    Waits
    Regular Price $95.00 Starting at $95.00
  26. Ormond
    Ormond
    Starting at $70.00
  27. Costa
    Costa
    Starting at $75.00
  28. Mink F24
    Riff
    Starting at $170.00
  29. Bailey - Java Bean
    Blixen
    Starting at $135.00
  30. Jackman
    Jackman
    Starting at $150.00
  31. Main Image
    Mannesroe
    Starting at $85.00
  32. Morgan
    Morgan
    Starting at $135.00
  33. Clayton
    Clayton
    Starting at $180.00
  34. Guthrie 7X
    Guthrie 7X
    Starting at $110.00
  35. Pecan
    Tombstone 2X
    Starting at $140.00
  36. Dillinger
    Dillinger
    Starting at $180.00

Items 1-36 of 60

Page
per page
Set Descending Direction

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!

FAQ

  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.