Men's Fedoras & Trilbies

Defined by classic shaping and tailored profiles, this selection offers fedoras and trilbies crafted for polished everyday wear or more refined occasions. Depending on availability, styles may include structured felts, lightweight straws, or modern interpretations with subtle detailing. Within Men’s Fedoras & Trilbies you’ll find silhouettes that balance timeless character with contemporary versatility across the Hats.com assortment. Other popular throwback styles include men's flat caps and men's pork pie hats.
  • Image of Racer Fedora product
    Bailey 1922

    Racer Fedora

    $225.00
    2 colors
  • Image of Emil Fedora product
    Bailey 1922

    Emil Fedora

    $225.00
    1 color
  • Image of Bystrom Fedora product
    Bailey 1922

    Bystrom Fedora

    $225.00
    2 colors
  • Image of Phineas Fedora product
    Bailey 1922

    Phineas Fedora

    $225.00
    2 colors
  • Image of Altair Fedora product
    Bailey 1922

    Altair Fedora

    $275.00
    1 color
  • Image of Horan Fedora product
    Bailey 1922

    Horan Fedora

    $240.00
    1 color
  • Image of Arion Fedora product
    Bailey 1922

    Arion Fedora

    $275.00
    1 color
  • Image of Hurtle Fedora product
    Bailey 1922

    Hurtle Fedora

    $225.00
    4 colors
  • Image of Coram Fedora product
    🇺🇸
    Bailey 1922

    Coram Fedora

    $240.00 $120.50
    1 color
  • Image of Boreal Fedora product
    50% off
    Bailey 1922

    Boreal Fedora

    $225.00 $112.50
    2 colors
  • Image of Billie Fedora product
    Kaminski

    Billie Fedora

    $295.00
    3 colors
  • Image of 414 Fedora product
    Exclusive
    Trimmed & Crowned

    414 Fedora

    $150.00
    2 colors

Frequently Asked Questions about Men's Fedoras & Trilbies

How should a man choose between a fedora and a trilby?

Consider your build and style. Fedoras with wider brims balance broader shoulders and frames. Trilbies with shorter brims suit slimmer builds and more compact outfits. Fedoras are more versatile; trilbies are more contemporary and casual.

What's the most versatile men's fedora material?

Wool felt in a neutral color (charcoal, grey, or navy) is the single most versatile choice. It works from fall through spring with everything from jeans to sport coats. Add a straw fedora for summer coverage.

Do men still wear fedoras?

Quality fedoras worn with the right outfits are timeless not trendy, not dated. The key is fit, material quality, and matching the hat to your clothing's formality. A well-chosen fedora adds genuine style.

What brim width works best for most men?

2.25 to 2.75 inches is the sweet spot for most men. This range provides enough brim to frame the face without overwhelming it. Broader men can go wider; slimmer men should stay at the narrower end.

How do I start wearing a fedora if I've never worn hats?

Start with a LiteFelt in a neutral color it's forgiving (crushable, water-resistant) and versatile. Wear it with an outfit you already feel confident in. The hat should complement, not transform, your existing style.