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 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 :)