No single person is more responsible for the fedora's status as a symbol of cool than Frank Sinatra. From the recording studio to the stage to the streets of Las Vegas, Ol' Blue Eyes wore his hat tilted just so — brim snapped down in front, worn with a suit and an attitude. It became as much a part of his image as the voice.
Sinatra's style has never really gone out of fashion, and the good news is that his signature hat is one of the most wearable classics you can own. Here's what made his look work — and how to build your own.
The snap-brim fedora (the Sinatra staple)
Sinatra's go-to was a snap-brim fedora — a medium-width brim you can snap down in front and up in back, paired with a center-dent or teardrop crown. Classic colors were charcoal, grey, and tan, usually with a contrasting band. A quality felt is what gives it that crisp, dressed-up line.
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Bailey of Hollywood Curtis Indy Fedora — a wool-felt fedora with the clean, snap-brim shape at the heart of the Sinatra look, made in the USA. -
Bailey of Hollywood Tino Crushable Fedora — a versatile crushable felt that travels well and keeps its sharp lines.
The dress fedora (for the tuxedo nights)
When Sinatra dressed to the nines, so did his hat. A structured wool-felt dress fedora is the piece that finishes a suit or a tux with old-school authority.
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Country Gentleman Frederick Wool Felt Fedora — a refined, made-in-the-USA dress fedora with timeless proportions. -
Country Gentleman Wilton Wool Fedora — a clean, classic felt that dresses up beautifully.
The wide-brim statement (the vintage Vegas look)
For a bolder, more theatrical take — the kind of hat that owns a room the way Sinatra owned a stage — go a little wider and more dramatic.
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Bailey of Hollywood Gangster Wool Felt (Capone Style) — a wide-brim, vintage-inspired felt with real mid-century presence.
Summer Sinatra
Come summer, the felt came off and a lighter hat went on. A straw fedora keeps the same silhouette with warm-weather breathability — perfect for the Palm Springs end of the Rat Pack lifestyle.
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Bailey of Hollywood Mannes Stingy Brim Fedora — a lightweight straw fedora with a trim, modern brim.
Wear it like Frank
The secret to the Sinatra look isn't just the hat — it's the tilt. Wear it slightly cocked, brim snapped down in front, with confidence. And make sure it fits: use our hat sizing guide to get it right.
Ready to do it your way? Explore the full fedora collection at Fedoras.com.
Fedoras.com is not affiliated with or endorsed by the Frank Sinatra estate. Style references are provided for inspiration only.
