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Fedoras & Trilbies

45 Items

per page
Set Descending Direction
  1. Bailey - Tan
    Imlay
    Regular Price $135.00 Starting at $101.25
  2. Casmir - Limited Edition - Coal/M
    Casmir - Limited Edition
    Starting at $398.00
  3. Bailey - Black
    Croft
    Starting at $185.00
  4. Bailey - Natural
    Orsun
    Starting at $125.00
  5. Bailey - Black
    Levon
    Starting at $185.00
  6. Bailey of Hollywood Dalton Safari Outback - Tan
    Dalton
    Starting at $70.00
  7. Bailey - Black
    Colter
    Starting at $185.00
  8. Azriel - Limited Edition - Black/M
    Azriel - Limited Edition
    Starting at $398.00
  9. Niles - Limited Edition - Camel/M
    Niles - Limited Edition
    Starting at $398.00
  10. Bailey Colby - Soft Khaki
    Colby
    Starting at $210.00
  11. Bailey Godwin-Ochre
    Godwin
    Regular Price $225.00 Starting at $150.00
  12. Alternate View
    Clafin
    Regular Price $175.00 Starting at $122.50
  13. Bailey honey
    Bevers
    Regular Price $175.00 Starting at $131.25
  14. Main Image
    Craig
    Regular Price $78.00 Starting at $58.50
  15. Ardit
    Ardit
    Regular Price $160.00 Starting at $120.00
  16. Hats - Black
    Billy
    Regular Price $75.00 Starting at $56.25
  17. Alternate View
    Magness
    Starting at $160.00
  18. Main Image
    Giger
    Starting at $175.00
  19. Brooks
    Brooks
    Regular Price $175.00 Starting at $87.50
  20. Cutler
    Cutler
    Regular Price $170.00 Starting at $127.50
  21. Bailey Natural
    Balans
    Regular Price $85.00 Starting at $63.75
  22. Main Image
    Mullan
    Regular Price $90.00 Starting at $67.50
  23. Bailey of Hollywood Spencer LiteStraw® Fedora - Natural
    Spencer
    Starting at $90.00
  24. Wilshire
    Wilshire
    Regular Price $85.00 Starting at $63.75
  25. Bailey of Hollywood Denney Fedora - Black
    Denney
    Starting at $83.00
  26. Brodnax - Black/S
    Brodnax
    Starting at $190.00
  27. Devers
    Devers
    Starting at $235.00
  28. Kirton
    Kirton
    Regular Price $170.00 Starting at $127.50
  29. Trinell
    Trinell
    Starting at $400.00
  30. Bailey of Hollywood Stansfield Panama Fedora - Natural
    Stansfield
    Regular Price $175.00 Starting at $122.50
  31. Parson
    Parson
    Regular Price $175.00 Starting at $131.25
  32. Limited Edition - Hillman - Coffee Beige String Swirl/S
    Limited Edition - Hillman
    Starting at $170.00
  33. Nelles
    Nelles
    Starting at $140.00
  34. Abbott
    Abbott
    Regular Price $130.00 Starting at $91.00
  35. Bailey of Hollywood Stedman Elite Velour Fedora - Camel
    Stedman
    Regular Price $168.00 Starting at $84.00
  36. Bailey of Hollywood Piston Fedora - Black
    Piston
    Starting at $80.00
  37. Bailey of Hollywood Codner Lanolux Fedora - Mink
    Codner
    Regular Price $130.00 Starting at $91.00
  38. Curtis Limited Edition Fedora - Raisin/S
    Exclusive - Curtis Limited Edition
    Regular Price $118.00 Starting at $73.50
  39. Bailey of Hollywood Flume Fedora - Aubergine
    Flume
    Starting at $350.00
  40. Blixen Limited Edition Fedora - Evening Sky/S
    Exclusive - Blixen Limited Edition
    Regular Price $118.00 Starting at $73.50
  41. Bogan
    Bogan
    Starting at $175.00
  42. Winters
    Winters
    Regular Price $145.00 Starting at $72.50
  43. Ammon
    Ammon
    Starting at $175.00
  44. Bailey of Hollywood Blixen LiteFelt® Fedora  - Black
    Blixen
    Regular Price $103.00 Starting at $72.09
  45. Main Image
    Cosmo
    Regular Price $138.00 Starting at $69.00

45 Items

per page
Set Descending Direction

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.