The man In the hat
Frank Sinatra

Like the Fedora, which it closely resembles, the Trilby took its name from a stage play. It typically has a narrower brim and a lower crown than the Fedora and is often worn further back on the head. The cool Trilby recently enjoyed a resurgence among artists and musicians.

The Trilby is the first proper hat for many men. It feels cool without seeming ostentatious. The low crown and narrow brim ensure it is unlikely to get knocked or blown off. And even the cheapest-made fashion Trilby can look pretty good.

Jon Hamm in Mad Men from 2007 - 2015
Bruno Mars