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Fedoras & Trilbies

28 Items

per page
Set Descending Direction
  1. Bailey - Black
    Starting at $80.00
  2. LANG Fedora - Avion / S
    Starting at $200.00
  3. Bailey - Black
    Regular Price $175.00 Starting at $131.25
  4. Bailey - Copper
    Starting at $375.00
  5. Bailey - Black
    Starting at $80.00
  6. Bailey - Black
    Starting at $140.00
  7. Bailey - Black
    Regular Price $130.00 Starting at $97.50
  8. Bailey - Natural
    Starting at $145.00
  9. Bailey Beaver
    Starting at $125.00
  10. Bailey Sterne - Soft Khaki
    Regular Price $170.00 Starting at $127.50
  11. Bailey Colby - Soft Khaki
    Regular Price $210.00 Starting at $157.50
  12. Brooks
    Regular Price $175.00 Starting at $87.50
  13. Bailey Camo
    Starting at $95.00
  14. Rothney
    Starting at $140.00
  15. Treport Fedora - Ink Blue/S
    Regular Price $135.00 Starting at $101.25
  16. Berle
    Starting at $105.00
  17. Ellett
    Starting at $180.00
  18. Barksdale
    Regular Price $195.00 Starting at $146.25
  19. Nelles
    Starting at $140.00
  20. Bailey of Hollywood Stedman Elite Velour Fedora - Camel
    Regular Price $168.00 Starting at $84.00
  21. Bailey of Hollywood Maglor Fedora - Navy
    Starting at $75.00
  22. Bailey of Hollywood Piston Fedora - Black
    Starting at $80.00
  23. Criss Limited Edition Fedora - Forest/S
    Exclusive - Criss Limited Edition
    Regular Price $155.00 Starting at $73.50
  24. Curtis Limited Edition Fedora - Raisin/S
    Exclusive - Curtis Limited Edition
    Regular Price $118.00 Starting at $59.00
  25. Bailey Main
    Draper III
    Starting at $375.00
  26. Bailey of Hollywood Riff Fedora - Black
    Regular Price $133.00 Starting at $66.50
  27. Bailey of Hollywood Wynn LiteFelt® Fedora - Pewter
    Regular Price $118.00 Starting at $88.50
  28. Curtis
    Regular Price $118.00 Starting at $59.00

28 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.