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Extended Sizes

Items 1-48 of 61

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  1. USA Desert Breeze Cowboy Hat
    USA Desert Breeze Cowboy Hat
    Starting at $60.00
  2. Bailey - Beige Stripe
    Starting at $90.00
  3. Hats - Bitter Chocolate
    Regular Price $170.00 Starting at $127.50
  4. Bailey Deepwoods Camo
    Starting at $125.00
  5. Bailey - Camel
    Starting at $112.00
  6. Bailey  - Cordova
    Regular Price $375.00 Starting at $281.25
  7. Bailey Pennswoods Camo
    Starting at $100.00
  8. Bailey - Espresso Check
    Starting at $225.00
  9. Ardit
    Regular Price $160.00 Starting at $80.00
  10. Ganey
    Starting at $75.00
  11. Bailey - Oak
    Regular Price $205.00 Starting at $153.75
  12. Codner
    Regular Price $130.00 Starting at $65.00
  13. Main Image
    Desert Knight
    Starting at $60.00
  14. Main Image
    Seneca 15X
    Starting at $100.00
  15. Main Image
    Farson 7X
    Starting at $80.00
  16. Main Image
    Shawnee 4X
    Starting at $70.00
  17. Zippo 2X
    Zippo 2X
    Starting at $130.00
  18. Hastings 4X
    Hastings 4X
    Regular Price $170.00 Starting at $127.50
  19. Main Image
    Regular Price $135.00 Starting at $67.50
  20. Lord Stripe
    Lord Stripe
    Regular Price $90.00 Starting at $45.00
  21. Salter
    Starting at $375.00
  22. Wind River® Caliber
    Wind River® Caliber
    Regular Price $130.00 Starting at $97.50
  23. Wheeler 3X
    Wheeler 3X
    Starting at $140.00
  24. Bailey - Blue
    Regular Price $85.00 Starting at $42.50
  25. Ormond
    Starting at $70.00
  26. Ricker
    Starting at $70.00
  27. Bailey -  Lazuli Blue
    Regular Price $150.00 Starting at $75.00
  28. Medium Brown Mix
    Regular Price $118.00 Starting at $59.00
  29. Jackman
    Regular Price $135.00 Starting at $87.75
  30. Main Image
    Starting at $85.00
  31. Clayton
    Starting at $180.00
  32. Guthrie 7X
    Guthrie 7X
    Starting at $110.00
  33. Pecan
    Tombstone 2X
    Starting at $140.00
  34. Eddy Bros.® Scottsdale Cowboy Western Hat - Black
    Eddy Bros.® Scottsdale
    Regular Price $70.00 Starting at $49.99
  35. Dillinger
    Starting at $180.00
  36. Cavalry II
    Cavalry II
    Starting at $140.00
  37. Hats - Red
    Lightning 4X
    Regular Price $185.00 Starting at $138.75
  38. Main Image
    Starting at $70.00
  39. Bailey Nordic Multi
    Regular Price $75.00 Starting at $37.50
  40. Bailey Fog
    Regular Price $75.00 Starting at $37.50
  41. Bailey - Ash
    Regular Price $85.00 Starting at $55.25
  42. Bailey - Flint Gray
    Regular Price $118.00 Starting at $59.00
  43. Bailey - Flint Gray
    Regular Price $118.00 Starting at $59.00
  44. Bailey - Kelp
    Regular Price $105.00 Starting at $52.50
  45. Hats - Ash
    Regular Price $115.00 Starting at $74.75
  46. Hanson
    Starting at $170.00
  47. Godfather
    Starting at $155.00
  48. Bailey - Italian Clay
    Regular Price $160.00 Starting at $120.00

Items 1-48 of 61

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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 $100. We also offer 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.