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Fedoras & Trilbies

Items 97-144 of 160

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  1. Hesmond
    Hesmond
    Regular Price $125.00 Starting at $62.50
  2. Main Image
    Mannesroe
    Starting at $85.00
  3. Treport
    Treport
    Regular Price $135.00 Starting at $67.50
  4. Bailey - Tawny
    Hester
    Regular Price $100.00 Starting at $50.00
  5. Shell
    Wilshire
    Regular Price $85.00 Starting at $42.50
  6. Burnell
    Burnell
    Regular Price $135.00 Starting at $67.50
  7. Freddy
    Freddy
    Regular Price $75.00 Starting at $37.50
  8. Hats - Natural
    Blackburn
    Regular Price $155.00 Starting at $77.50
  9. Horsup
    Horsup
    Regular Price $125.00 Starting at $62.50
  10. Denney
    Denney
    Starting at $95.00
  11. Bailey Tan
    Relik
    Starting at $185.00
  12. Walnut
    Foley
    Regular Price $85.00 Starting at $42.50
  13. Brodnax
    Brodnax
    Regular Price $210.00 Starting at $157.50
  14. Konrath
    Konrath
    Starting at $180.00
  15. Bailey Kapok Green
    Berle
    Starting at $105.00
  16. Bailey of Hollywood Roll Up II Panama Fedora - Natural
    Roll Up II
    Starting at $240.00
  17. Bailey - Avion
    Ellett
    Starting at $200.00
  18. Loring
    Loring
    Starting at $375.00
  19. bailey main
    Devers
    Regular Price $235.00 Starting at $117.50
  20. Bailey of Hollywood Salter Panama Fedora - Natural
    Salter
    Starting at $375.00
  21. Bailey Barksdale - Whiskey
    Barksdale
    Regular Price $195.00 Starting at $97.50
  22. Kirton
    Kirton
    Regular Price $170.00 Starting at $85.00
  23. Hooper
    Hooper
    Starting at $90.00
  24. Blume
    Blume
    Regular Price $85.00 Starting at $42.50
  25. Trinell
    Trinell
    Regular Price $475.00 Starting at $356.25
  26. Bailey - Taupe
    Stansfield
    Regular Price $175.00 Starting at $87.50
  27. Derian
    Derian
    Starting at $135.00
  28. Bailey - Ink Stain
    Parson
    Regular Price $175.00 Starting at $87.50
  29. Tate
    Tate
    Starting at $80.00
  30. Main Image
    Rokit
    Starting at $80.00
  31. Bailey - Natural/Earth
    Cuban
    Regular Price $180.00 Starting at $90.00
  32. Bailey of Hollywood Anderson LiteStraw® Fedora - Natural
    Anderson
    Regular Price $145.00 Starting at $72.50
  33. Tessier
    Tessier
    Starting at $220.00
  34. Nelles
    Nelles
    Starting at $165.00
  35. Abbott
    Abbott
    Regular Price $130.00 Starting at $65.00
  36. Auman
    Auman
    Regular Price $450.00 Starting at $337.50
  37. Girvin
    Girvin
    Regular Price $425.00 Starting at $318.75
  38. Bailey - Oak
    Stedman
    Regular Price $205.00 Starting at $153.75
  39. Maglor
    Maglor
    Starting at $75.00
  40. Kisner
    Kisner
    Starting at $175.00
  41. Piston
    Piston
    Starting at $80.00
  42. Codner
    Codner
    Regular Price $130.00 Starting at $65.00
  43. Main Image
    Ralat
    Starting at $450.00
  44. Flume
    Flume
    Regular Price $375.00 Starting at $281.25
  45. Hats - Honey
    Colver
    Regular Price $185.00 Starting at $99.99
  46. Hats - Greige
    Barkley
    Regular Price $150.00 Starting at $75.00
  47. Hats - Almond
    Bogan
    Regular Price $193.00 Starting at $144.75
  48. Hats - Almond
    Winters
    Regular Price $193.00 Starting at $144.75

Items 97-144 of 160

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Hollywood Shop By Style: Fedoras & Trilbies 

There’s something about a fedora or trilby that’s effortlessly suave. At Bailey Hats, we bring you the widest selection of fedoras and trilbies in classic Hollywood style. Shop our fedora and trilby hats for sale to find a classic, modern, and timeless touch to cap off your outfit.

Both our fedoras and trilbies come in various colors, shapes, and sizes. We carefully tailor every hat shape for an incomparable fit. Choose from various fabrics, like wool felt for warmth or genuine panama for lightweight summer wear. 

 

Fedora-Style Hats — Timeless Style and Character

Our fedoras offer timeless style and character. Choose a short-brimmed fedora for a more casual look paired with jeans, tees, shorts, or khakis, or pick a long-brimmed fedora to add the finishing touch to your suit or formal wear. 

Whether you want to complete your formalwear ensemble or add some flair, our fedoras will do the trick. Add a fedora-style hat to your collection for a sophisticated look on any occasion.

 

Trilbies — Charm and Style

Our trilby hats for sale are perfect for anyone who wants to look stylish without being too formal. Trilby hats are characterized by their snap-brim that falls just above the eyebrows and flares out at a slight angle, creating an irresistible charm with laid-back style. 

We make our trilbies with straw, wool felt, braids, and genuine Panama straw. They’re finished with various accents for that perfect personalized touch.

Our trilby hats are the perfect accessory for anyone who loves the timeless statement of fedora-style hats, but prefers a more laid-back look. The trilby is the crowning jewel of any outfit and can be worn with any look, from a business suit to denim.

 

Shop Now at Bailey Hats

Whether you're looking to upgrade your winter headwear or add some summer fedora-style hats to your collection, Bailey Hats has the perfect hat for you. The Bailey style is all about cool with a contemporary touch and vintage feels reimagined for today’s modern man. Explore our fedora and trilby hats for sale and express yourself with a one-of-a-kind style that’s uniquely you.