For me, it always makes me think of the 50's & early '60's (that's the 1950's and the early 1960's).
Visions of Sean Connery
or Frank Sinatra .
All men wore hats then and the type of hat they wore said alot about the kind of guy they were. Obviously they were very cool.
The Trilby is a felt hat, with a narrow brim with a crown that has a deep indent. It has been a fashion statement for men and women for a very long time. George Du Maurier wrote a novel called "Trilby" in 1894 which became a play a year later. The Hat is named after the main character, and became famous because the actress playing the part of "Trilby" wore one .
Now tell me these hats are not cool, debonair and sauve!!!! (Even though there is a Fedora thrown in there.
But... just like anything else, not everyone should be wearing one :)