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

Fedoras & Trilbies

Items 1-48 of 80

Page
per page
Set Descending Direction
  1. Bailey - Black
    Rask
    Starting at $200.00
  2. Bailey - Natural
    Braylon
    Starting at $145.00
  3. Casmir - Limited Edition - Coal/M
    Casmir - Limited Edition
    Starting at $398.00
  4. Bailey - Natural
    Orsun
    Starting at $125.00
  5. Bailey - Natural
    Glaser
    Starting at $175.00
  6. Bailey - Black
    Eli
    Regular Price $85.00 Starting at $63.75
  7. Bailey of Hollywood Dalton Safari Outback - Tan
    Dalton
    Starting at $70.00
  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 Sterne - Soft Khaki
    Sterne
    Starting at $170.00
  11. Bailey Acker- Midnight Brown
    Acker
    Starting at $135.00
  12. Bailey Lund - Black
    Lund
    Starting at $140.00
  13. Bailey Clorindon - Black
    Clorindon
    Starting at $215.00
  14. Bailey Ernest - Black
    Ernest
    Starting at $180.00
  15. Bailey Colby - Soft Khaki
    Colby
    Starting at $210.00
  16. Bailey Godwin - Black
    Godwin
    Regular Price $225.00 Starting at $150.00
  17. Bailey Cavalier - Black
    Cavalier
    Starting at $400.00
  18. Bailey Architect - Black
    The Architect
    Starting at $425.00
  19. Main Image
    Craig
    Regular Price $78.00 Starting at $58.50
  20. Hats - Black
    Billy
    Regular Price $75.00 Starting at $56.25
  21. Alternate View
    Derwent
    Regular Price $175.00 Starting at $131.25
  22. Bailey of Hollywood Mannes Braided Trilby - Navy Multi
    Mannes
    Regular Price $75.00 Starting at $37.50
  23. Brooks
    Brooks
    Regular Price $175.00 Starting at $116.25
  24. Bailey Charcoal/Rust
    Warlick
    Starting at $200.00
  25. Bailey Camo
    Westfield
    Starting at $85.00
  26. Rothney
    Rothney
    Starting at $120.00
  27. Salem Braided Fedora - Black/L
    Salem
    Starting at $75.00
  28. Main Image
    Mullan
    Regular Price $90.00 Starting at $67.50
  29. Hesmond
    Hesmond
    Regular Price $125.00 Starting at $93.75
  30. Bailey of Hollywood Mannesroe Braided Fedora - Black/Charcoal Multi
    Mannesroe
    Starting at $75.00
  31. Treport Fedora - Ink Blue/S
    Treport
    Starting at $135.00
  32. Bailey of Hollywood Hester Fedora - Copper
    Hester
    Regular Price $90.00 Starting at $67.50
  33. Wilshire
    Wilshire
    Regular Price $85.00 Starting at $63.75
  34. Bailey of Hollywood Freddy Fedora - Black
    Freddy
    Regular Price $75.00 Starting at $56.25
  35. Marack Fedora - Black/S
    Marack
    Regular Price $140.00 Starting at $93.75
  36. Rovner Fedora - Black/S
    Rovner
    Regular Price $115.00 Starting at $86.25
  37. Bailey of Hollywood Denney Fedora - Black
    Denney
    Starting at $83.00
  38. Brodnax - Black/S
    Brodnax
    Starting at $190.00
  39. Berle
    Berle
    Starting at $95.00
  40. Ellett
    Ellett
    Regular Price $180.00 Starting at $112.50
  41. Barksdale
    Barksdale
    Starting at $195.00
  42. Romeo
    Romeo
    Regular Price $100.00 Starting at $75.00
  43. Trinell
    Trinell
    Starting at $400.00
  44. Tate
    Tate
    Starting at $70.00
  45. Bascom
    Bascom
    Regular Price $100.00 Starting at $75.00
  46. Busken Polished Fedora - Black/S
    Busken
    Regular Price $143.00 Starting at $100.10
  47. Nelles
    Nelles
    Starting at $140.00
  48. Abbott
    Abbott
    Regular Price $130.00 Starting at $97.50

Items 1-48 of 80

Page
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.