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.
Filter
25% off
Bailey 1922
Ammon Fedora
original price$99.00sale price$74.25
7 colors
new colors
Bailey 1922
Sperling LiteFelt® Fedora
price$185.00
7 colors
Bailey 1922
Criss Fedora
original price$175.00sale price$119.00
6 colors
Bailey 1922
Salter Panama Fedora
price$375.00
1 color
Bailey 1922
Loring Panama Fedora
price$375.00
1 color
top seller
Bailey 1922
Foley Fedora
price$95.00
1 color
Bailey 1922
Berle Fedora
price$105.00
4 colors
Bailey 1922
Draper III Fedora
price$500.00
4 colors
Bailey 1922
Roll Up II Panama Fedora
price$250.00
1 color
Country Gentleman
Floyd Fedora
price$70.00
2 colors
Bailey 1922
Blackburn LiteStraw® Fedora
original price$155.00sale price$72.50
4 colors
20% off
Country Gentleman
Joey Braided Fedora
original price$50.00sale price$39.99
4 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.
Choosing a selection results in a full page refresh.