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Floppy Hats - Derbies & Bowlers

Floppy Hats - Derbies & Bowlers
Fashionable while also being great for blocking the sun, our floppy hats feature large, wide brims and deep-sitting crowns. With that perfect face-shading look of a draping brim, floppy hats can help you achieve everything from a bohemian chic appearance to an elegant, swanky presence. Favored by celebrities like Blake Lively, Sofia Vergara, and Jennifer Lopez, the floppy hat has become an important part of every stylish wardrobe.
In many instances, the saying "They just don't make 'em like they used to" rings very true. The hat world is one place where this isn't accurate, as long as you know where to look. Our derby and bowler selection is stocked full of some of the coolest traditional hats in the world. By crafting hats by hand with the same methods that have always been used, brands like Bollman Hat Company (America's oldest hatmaker) continue to lead the way in fine headwear. Derbies and bowlers are round crown styles with a stingy turn-up brim. They are wonderful for attaining an absolutely timeless look. These shapes and designs have been popular for decades, and in some cases, even centuries!

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  • Wool Bombin

    Wool Bombin

    by Kangol

    See more Colors, including:
    RedGreyBlackYellow
    S, M, L, XL
    $65.00
  • Macey Floppy Wide Brim Hat

    Macey Floppy Wide Brim Hat

    by Goorin Bros.

    See more Colors, including:
    BlackGreyNatural
    S, M, L

    Regular Price: $55.00

    Special Price: $41.25

  • Canvas Floppy Wide Brim

    Canvas Floppy Wide Brim

    by Sperry

    See more Colors, including:
    Red
    One Size Fits Most

    Regular Price: $32.00

    Special Price: $24.00

  • Violet Floppy Wide Brim

    Violet Floppy Wide Brim

    by Betmar

    Available Sizes:
    One Size Fits Most

    Regular Price: $70.00

    Special Price: $52.50

  • Copley Derby

    Copley Derby

    by Bailey of Hollywood

    See more Colors, including:
    Black
    M, L, XL

    Regular Price: $175.00

    Special Price: $131.25

  • Jarvis Derby

    Jarvis Derby

    by Bailey of Hollywood

    See more Colors, including:
    Grey
    S, M, L, XL

    Regular Price: $118.00

    Special Price: $88.50

  • Origin Bowler

    Origin Bowler

    by Kangol

    See more Colors, including:
    GreyBlack
    S, M, L, XL

    Regular Price: $130.00

    Special Price: $97.50

  • Space Bombin

    Space Bombin

    by Kangol

    See more Colors, including:
    GreyBlackGreen
    M

    Regular Price: $120.00

    Special Price: $90.00

  • Wool Bombin

    Wool Bombin

    by Kangol

    See more Colors, including:
    Black
    L, M, S, XL

    Regular Price: $70.00

    Special Price: $52.50

  • Joan Floppy Wide Brim Hat

    Joan Floppy Wide Brim Hat

    by Betmar

    See more Colors, including:
    BlackRedBlue
    One Size Fits Most

    Regular Price: $80.00

    Special Price: $60.00

  • Estate Bowler

    Estate Bowler

    by Kangol

    See more Colors, including:
    GreyBlackBrown
    S, M, L, XL

    Regular Price: $120.00

    Special Price: $90.00

  • Charlie Floppy Brim Fedora

    Charlie Floppy Brim Fedora

    by Betmar

    See more Colors, including:
    BlackGreenBrown
    S/M, M/L

    Regular Price: $115.00

    Special Price: $86.25

  • Charles GentleFelt® Bowler

    Charles GentleFelt® Bowler

    by Country Gentleman

    See more Colors, including:
    Black
    M, L, XL

    Regular Price: $60.00

    Special Price: $45.00

  • Cindy Floppy Wide Brim Hat

    Cindy Floppy Wide Brim Hat

    by Betmar

    See more Colors, including:
    BlackRedGreen
    S/M, M/L

    Regular Price: $110.00

    Special Price: $82.50

  • English Derby Hat

    English Derby Hat

    by Bailey of Hollywood

    See more Colors, including:
    Black
    6 3/4, 6 7/8, 7, 7 1/2, 7 1/4, 7 1/8, 7 3/8, 7 5/8

    Regular Price: $225.00

    Special Price: $168.75

Set Descending Direction

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