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 Foley Fedora - Past Season product
    25% off
    Bailey 1922

    Foley Fedora - Past Season

    $95.00 $71.25
    1 color
  • Image of Billy Trilby product
    50% off
    Bailey 1922

    Billy Trilby

    $85.00 $42.50
    7 colors
  • Image of Jackman Fedora product
    Bailey 1922

    Jackman Fedora

    $135.00 $81.50
    1 color
  • Image of Classic LiteFelt® Fedora product
    30% off
    Bailey 1922

    Classic LiteFelt® Fedora

    $130.00 $91.50
    2 colors
  • Image of Eli Fedora product
    55% off
    Bailey 1922

    Eli Fedora

    $95.00 $42.50
    3 colors
  • Image of Ganon Fedora product
    25% off
    Bailey 1922

    Ganon Fedora

    $245.00 $183.75
    2 colors
  • Image of Dayton Raindura® Outback product
    25% off
    Bailey Western

    Dayton Raindura® Outback

    $138.00 $103.50
    1 color
  • Image of Hester Braided Fedora product
    25% off
    Bailey 1922

    Hester Braided Fedora

    $100.00 $75.00
    2 colors
  • Image of Curtis LiteFelt® Fedora product
    50% off
    Bailey 1922

    Curtis LiteFelt® Fedora

    $135.00 $67.50
    10 colors
  • Image of Tino Fedora product
    sale
    Bailey 1922

    Tino Fedora

    $135.00 $47.25
    2 colors
  • Image of Riff Fedora product
    50% off
    Bailey 1922

    Riff Fedora

    $170.00 $85.50
    2 colors
  • Image of Blixen Fedora product
    50% off
    Bailey 1922

    Blixen Fedora

    $130.00 $64.50
    6 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.