End of Season Blowout Sale | Additional 15% Off Sale Category

Fedoras & Trilbies

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  1. Bailey - Natural
    Braylon
    Starting at $145.00
  2. Casmir - Limited Edition - Coal/M
    Casmir - Limited Edition
    Starting at $398.00
  3. Bailey - Natural/Black
    Telfar
    Regular Price $150.00 Starting at $112.50
  4. Bailey - Natural
    Orsun
    Starting at $125.00
  5. Bailey - Natural
    Glaser
    Starting at $175.00
  6. Bailey - Brown
    Dario
    Regular Price $95.00 Starting at $71.25
  7. Azriel - Limited Edition - Black/M
    Azriel - Limited Edition
    Starting at $398.00
  8. Niles - Limited Edition - Camel/M
    Niles - Limited Edition
    Starting at $398.00
  9. Bailey Sterne - Soft Khaki
    Sterne
    Starting at $170.00
  10. Bailey Colby - Soft Khaki
    Colby
    Starting at $210.00
  11. Main Image
    Craig
    Regular Price $78.00 Starting at $58.50
  12. Bailey Natural
    Verrett
    Regular Price $150.00 Starting at $112.50
  13. Ardit
    Ardit
    Regular Price $160.00 Starting at $120.00
  14. Bailey of Hollywood Outen LiteStraw® Fedora - Natural
    Outen
    Regular Price $120.00 Starting at $90.00
  15. Main Image
    Tasmin
    Regular Price $175.00 Starting at $131.25
  16. Alternate View
    Magness
    Starting at $160.00
  17. Jansen
    Jansen
    Regular Price $200.00 Starting at $150.00
  18. Main Image
    Halpern
    Regular Price $170.00 Starting at $127.50
  19. Bailey Natural/Camo
    Breten
    Regular Price $135.00 Starting at $86.25
  20. Bailey of Hollywood Mannes Braided Trilby - Navy Multi
    Mannes
    Regular Price $75.00 Starting at $37.50
  21. Brooks
    Brooks
    Regular Price $175.00 Starting at $116.25
  22. Cutler
    Cutler
    Regular Price $170.00 Starting at $127.50
  23. Bailey Camo
    Westfield
    Starting at $85.00
  24. Guthrie
    Guthrie
    Regular Price $140.00 Starting at $97.50
  25. Bailey Natural
    Balans
    Regular Price $85.00 Starting at $63.75
  26. Bailey of Hollywood Elliot Panama Straw Trilby - Natural
    Elliott
    Starting at $65.00
  27. Rothney
    Rothney
    Starting at $120.00
  28. Salem Braided Fedora - Black/L
    Salem
    Starting at $75.00
  29. Hanson
    Hanson
    Regular Price $140.00 Starting at $97.50
  30. Bailey Main
    Dreyer
    Regular Price $125.00 Starting at $93.75
  31. Lowden
    Lowden
    Regular Price $130.00 Starting at $97.50
  32. Bailey of Hollywood Spencer LiteStraw® Fedora - Natural
    Spencer
    Starting at $90.00
  33. Hesmond
    Hesmond
    Regular Price $125.00 Starting at $93.75
  34. Costigan
    Costigan
    Regular Price $135.00 Starting at $90.00
  35. Treport Fedora - Ink Blue/S
    Treport
    Starting at $135.00
  36. Bailey of Hollywood Hester Fedora - Copper
    Hester
    Regular Price $90.00 Starting at $67.50
  37. Burnell
    Burnell
    Starting at $135.00
  38. Bailey of Hollywood Freddy Fedora - Black
    Freddy
    Regular Price $75.00 Starting at $56.25
  39. Bailey of Hollywood Rudi LiteStraw® Fedora - Sepia/Natural
    Rudi
    Regular Price $175.00 Starting at $131.25
  40. Blackburn LiteStraw® Fedora - Natural/S
    Blackburn
    Regular Price $155.00 Starting at $105.00
  41. Bailey of Hollywood Horsup Fedora - Natural
    Horsup
    Regular Price $125.00 Starting at $93.75
  42. Bailey of Hollywood Relik LiteStraw® Fedora - Natural
    Relik
    Starting at $150.00
  43. Foley
    Foley
    Regular Price $85.00 Starting at $63.75
  44. Bailey of Hollywood Bristol Raindura® Fedora - Burlap
    Bristol
    Regular Price $125.00 Starting at $93.75
  45. Bailey of Hollywood Konrath Litestraw® Trilby - Natural
    Konrath
    Starting at $160.00
  46. Berle
    Berle
    Starting at $95.00
  47. Bailey of Hollywood Roll Up II Panama Fedora - Natural
    Roll Up II
    Starting at $230.00
  48. Ellett
    Ellett
    Regular Price $180.00 Starting at $112.50

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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.