12 Days of Gifting: 25% Off Select Winter Styles*

Fedoras & Trilbies

Items 1-36 of 66

Page
per page
Set Descending Direction
  1. Bailey - Avion
    Giles
    Starting at $225.00
  2. Bailey - Avion
    Crispin
    Regular Price $240.00 Starting at $180.00
  3. Hats - Avion Window
    Emil
    Starting at $225.00
  4. Bailey - Avion/Natural
    Phineas
    Starting at $225.00
  5. Bailey - Black
    Hurtle
    Starting at $225.00
  6. Bailey - Avion
    Coram
    Regular Price $240.00 Starting at $180.00
  7. Bailey - Dark Natural
    Adlay
    Regular Price $135.00 Starting at $101.25
  8. Bailey - Black
    Rask
    Starting at $225.00
  9. Bailey - Rust
    Hinx
    Starting at $225.00
  10. Bailey - Flint Gray
    Appley
    Starting at $200.00
  11. Bailey - Natural
    Alix
    Starting at $250.00
  12. Rawn Fedora - Elemental Blue / S
    Rawn
    Regular Price $160.00 Starting at $120.00
  13. Bailey Deepwoods Camo
    Opsec
    Starting at $145.00
  14. Bailey - Copper
    Nilson
    Starting at $450.00
  15. Bailey - Black
    Croft
    Starting at $210.00
  16. Bailey - Black
    Conlon
    Starting at $200.00
  17. LANG Fedora - Avion / S
    Lang
    Starting at $225.00
  18. Bailey - Black
    Cyd
    Starting at $155.00
  19. Bailey - Bone
    Ganon
    Starting at $245.00
  20. Bailey - Kelp
    Lasham
    Starting at $155.00
  21. Bailey - Sea Moss
    Sprake
    Starting at $185.00
  22. Klinger Fedora - Kelp / S
    Klinger
    Regular Price $170.00 Starting at $127.50
  23. Bailey - Natural
    Orsun
    Starting at $150.00
  24. Bailey - Black
    Eli
    Starting at $95.00
  25. Bailey Beaver
    EDC
    Starting at $100.00
  26. Bailey - Whiskey
    Darwin
    Starting at $260.00
  27. Bailey - Black
    Syden
    Starting at $160.00
  28. Bailey - Natural
    Moren
    Starting at $250.00
  29. Chalk
    Reeder
    Starting at $195.00
  30. Began Fedora - Dark Navy Swirl / S
    Began
    Starting at $175.00
  31. Bailey of Hollywood Dalton Safari Outback - Tan
    Dalton
    Starting at $75.00
  32. Bailey Godwin - Black
    Godwin
    Starting at $260.00
  33. Bailey Architect - Black
    Architect
    Starting at $460.00
  34. Main Image
    Craig
    Starting at $85.00
  35. Hats - Black
    Billy
    Starting at $85.00
  36. Main Image
    Giger
    Starting at $215.00

Items 1-36 of 66

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.