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 Barksdale Fedora product
    75% off
    Bailey 1922

    Barksdale Fedora

    $195.00 $48.75
    3 colors
  • Image of Trinell Fedora product
    25% off
    Bailey 1922

    Trinell Fedora

    $475.00 $356.50
    2 colors
  • Image of Ronit Fedora product
    25% off
    Bailey 1922

    Ronit Fedora

    $90.00 $67.50
    2 colors
  • Image of Rothney Raindura® Fedora product
    Bailey 1922

    Rothney Raindura® Fedora

    $140.00
    2 colors
  • Image of Hesmond Fedora product
    70% off
    Bailey 1922

    Hesmond Fedora

    $125.00 $37.50
    3 colors
  • Image of Ardit Fedora product
    70% off
    Bailey 1922

    Ardit Fedora

    $160.00 $48.00
    3 colors
  • Image of Jansen Fedora product
    70% off
    Bailey 1922

    Jansen Fedora

    $200.00 $60.00
    1 color
  • Image of Fry Fedora product
    Exclusive
    Bollman Hat Company

    Fry Fedora

    $300.00 $150.00
    1 color
  • Image of Bollman Fedora product
    Exclusive
    Bollman Hat Company

    Bollman Fedora

    $300.00 $150.00
    1 color
  • Image of Nelles LiteFelt® Fedora product
    Bailey 1922

    Nelles LiteFelt® Fedora

    $180.00
    5 colors
  • Image of Denney Fedora product
    50% off
    Bailey 1922

    Denney Fedora

    $95.00 $47.50
    2 colors
  • Image of Hester Fedora product
    Bailey 1922

    Hester Fedora

    $100.00
    7 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.