The 2023 Gift Guide is Here: Explore Now

Fedoras & Trilbies

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  1. Bailey - Black
    Scorsby
    Starting at $100.00
  2. Racer Fedora - Ash / S
    Racer
    Starting at $225.00
  3. Altair Fedora - Ash / S
    Altair
    Starting at $240.00
  4. Anker Fedora - Natural / S
    Anker
    Starting at $165.00
  5. Bailey - Senate
    Limited Edition - Tarleton
    Starting at $450.00
  6. Bailey - Rust
    Hinx
    Starting at $225.00
  7. Bailey - Flint Gray
    Nash
    Starting at $220.00
  8. Bailey - Flint Gray
    Appley
    Starting at $195.00
  9. Bailey - Copper
    Nilson
    Starting at $425.00
  10. Bailey - Black
    Croft
    Starting at $200.00
  11. Bailey - Black
    Thaler
    Regular Price $80.00 Starting at $60.00
  12. Bailey - Rosewood
    Kinns
    Starting at $145.00
  13. Bailey - Black
    Eli
    Regular Price $85.00 Starting at $55.25
  14. Bailey - Black
    Trevel
    Regular Price $240.00 Starting at $180.00
  15. Bailey - Black
    Colter
    Regular Price $205.00 Starting at $153.75
  16. Bailey - Black
    Erler
    Regular Price $130.00 Starting at $91.00
  17. Bailey - Black
    Caprole
    Regular Price $145.00 Starting at $108.75
  18. Bailey Colby - Soft Khaki
    Colby
    Regular Price $210.00 Starting at $157.50
  19. Main Image
    Craig
    Regular Price $78.00 Starting at $50.70
  20. Hats - Black
    Billy
    Regular Price $75.00 Starting at $48.75
  21. Alternate View
    Magness
    Regular Price $180.00 Starting at $135.00
  22. Bailey of Hollywood Mannes Braided Trilby - Navy Multi
    Mannes
    Regular Price $75.00 Starting at $48.75
  23. Brooks
    Brooks
    Regular Price $175.00 Starting at $113.75
  24. Bailey Charcoal/Rust
    Warlick
    Starting at $215.00
  25. Bailey - Mushroom
    Balans
    Regular Price $100.00 Starting at $75.00
  26. Salem Braided Fedora - Black/L
    Salem
    Regular Price $85.00 Starting at $63.75
  27. Bailey Main
    Dreyer
    Regular Price $125.00 Starting at $81.25
  28. Bailey of Hollywood Spencer LiteStraw® Fedora - Natural
    Spencer
    Regular Price $115.00 Starting at $86.25
  29. Mannesroe Braided Fedora - Black/Charcoal Multi/L
    Mannesroe
    Starting at $85.00
  30. Bailey of Hollywood Hester Fedora - Copper
    Hester
    Regular Price $100.00 Starting at $50.00
  31. Hats - Natural
    Blackburn
    Regular Price $155.00 Starting at $100.75
  32. Marack Fedora - Black/S
    Marack
    Regular Price $140.00 Starting at $70.00
  33. Hooper
    Hooper
    Starting at $90.00
  34. Blume
    Blume
    Regular Price $85.00 Starting at $55.25
  35. Bailey of Hollywood Stansfield Panama Fedora - Natural
    Stansfield
    Regular Price $175.00 Starting at $99.99
  36. Tate
    Tate
    Starting at $80.00
  37. Limited Edition - Hillman - Coffee Beige String Swirl/S
    Limited Edition - Hillman
    Regular Price $170.00 Starting at $51.00
  38. Abbott
    Abbott
    Regular Price $130.00 Starting at $65.00
  39. Kisner Open Crown - Black/S
    Kisner
    Starting at $175.00
  40. Bailey of Hollywood Bartham Elite Fedora - Chestnut
    Bartham
    Regular Price $185.00 Starting at $92.50
  41. Bailey of Hollywood Ralat Fedora - Black
    Ralat
    Starting at $450.00
  42. Hats - Pale Black
    Barkley
    Regular Price $150.00 Starting at $75.00
  43. Hats - Black
    Bogan
    Regular Price $193.00 Starting at $144.75
  44. Hats - Black
    Winters
    Regular Price $193.00 Starting at $144.75
  45. Hats - Almond
    Ammon
    Regular Price $193.00 Starting at $144.75
  46. Jackman
    Jackman
    Regular Price $135.00 Starting at $101.25
  47. Bailey of Hollywood Sperling LiteFelt® Fedora - Bluestone
    Sperling
    Regular Price $170.00 Starting at $127.50
  48. Bailey Main
    Draper III
    Starting at $410.00

Items 1-48 of 55

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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.