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Bowlers & Derbies

8 Items

per page
Set Descending Direction
  1. Bailey - Natural
    Starting at $195.00
  2. Bailey - Tawny/Black
    Starting at $250.00
  3. Chaplin
    Starting at $200.00
  4. Bailey - java Bean
    Starting at $400.00
  5. Bailey - Rosewood
    Regular Price $150.00 Starting at $112.50
  6. Bailey - Flint Gray
    Regular Price $170.00 Starting at $127.50
  7. Bailey - Italian Clay
    Regular Price $160.00 Starting at $120.00
  8. Bailey Main
    Starting at $155.00

8 Items

per page
Set Descending Direction

Hollywood Shop By Style: Bowlers & Derbies

Once the first choice of sophisticated London gentlemen, derbies and bowlers now offer the modern man a vintage look with a unique style. Shop derbies and bowlers that will delight you.

We craft every derby and bowler-style hat with high-quality materials, like wool felt and panama straw, and finish them with a classic grosgrain bow. Removable feathers allow you to customize the look, and comfort sweatbands and carefully designed shapes create exceptionally comfortable hats you can wear all day.


Vintage Styling with Derby-Style Hats

Derby-style hats gained popularity late in the 19th century. London gentlemen adopted them as a more casual alternative to top hats — so much so that derbies eventually became associated with the Brits. 

Harken back to that era and make a vintage statement with beautifully shaped derbies made for the modern world, or choose a sleeker look for a twist on the classic derby.


Versatile and Innovative

Create an iconic look with a classic bowler hat. Bowler hats are a versatile option for classic, formal, or more casual styles. Pair your bowler-style hat with a suit or formal wear, or style it with a tee and shorts to switch up a casual look. 


Express Your Style with Derbies and Bowlers

You have your own style. That’s why we’ve designed our derbies and bowlers with unexpected elements, like modern silhouettes and innovative materials. Whether you’re looking for classic or modern, we have derby-style hats and bowlers to express your individuality. 


See the Look at Bailey Hats

At Bailey Hats, we strive to make planning outfits easy and fun. We carry the latest hat trends in fashion while providing timeless classics that never go out of style. Shop the look and find handcrafted pieces that complement your personal style.