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Fedoras & Trilbies

32 Items

per page
Set Descending Direction
  1. Bailey - Natural
    Kai
    Regular Price $100.00 Starting at $60.00
  2. Bailey - Black
    Trope
    Regular Price $80.00 Starting at $60.00
  3. Bailey - tan
    Imlay
    Regular Price $135.00 Starting at $67.50
  4. Bailey - Natural/Black
    Telfar
    Regular Price $150.00 Starting at $75.00
  5. Bailey - Uniform Green
    Conlon
    Regular Price $175.00 Starting at $87.50
  6. Bailey - Nickel
    Thaler
    Regular Price $80.00 Starting at $60.00
  7. Bailey - Bloodstone
    Eli
    Regular Price $85.00 Starting at $42.50
  8. Bailey - Oak
    Levon
    Regular Price $185.00 Starting at $92.50
  9. Bailey - Satin Brass
    Erler
    Regular Price $130.00 Starting at $65.00
  10. Niles - Limited Edition
    Niles - Limited Edition
    Regular Price $398.00 Starting at $199.00
  11. Bailey Sterne - Soft Khaki
    Sterne
    Regular Price $170.00 Starting at $85.00
  12. 37188BH-Bailey-1922-COLBY-Fedora-NICKEL-1B.jpg
    Colby
    Regular Price $210.00 Starting at $105.00
  13. Bailey - Tawny
    Craig
    Regular Price $78.00 Starting at $39.00
  14. Bailey Main
    Verrett
    Regular Price $150.00 Starting at $75.00
  15. Bailey Fog
    Billy
    Regular Price $75.00 Starting at $37.50
  16. Alternate View
    Derwent
    Regular Price $175.00 Starting at $87.50
  17. Bailey Nordic Multi
    Mannes
    Regular Price $75.00 Starting at $37.50
  18. Bailey Main
    Dreyer
    Regular Price $125.00 Starting at $62.50
  19. Hesmond
    Hesmond
    Regular Price $125.00 Starting at $62.50
  20. Treport
    Treport
    Regular Price $135.00 Starting at $67.50
  21. Burnell
    Burnell
    Regular Price $135.00 Starting at $67.50
  22. Freddy
    Freddy
    Regular Price $75.00 Starting at $37.50
  23. Horsup
    Horsup
    Regular Price $125.00 Starting at $62.50
  24. Walnut
    Foley
    Regular Price $85.00 Starting at $42.50
  25. bailey main
    Devers
    Regular Price $235.00 Starting at $117.50
  26. Bailey Barksdale - Whiskey
    Barksdale
    Regular Price $195.00 Starting at $97.50
  27. Kirton
    Kirton
    Regular Price $170.00 Starting at $85.00
  28. Blume
    Blume
    Regular Price $85.00 Starting at $42.50
  29. Bailey of Hollywood Anderson LiteStraw® Fedora - Natural
    Anderson
    Regular Price $145.00 Starting at $72.50
  30. Abbott
    Abbott
    Regular Price $130.00 Starting at $65.00
  31. Codner
    Codner
    Regular Price $130.00 Starting at $65.00
  32. Yates
    Yates
    Regular Price $95.00 Starting at $47.50

32 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.