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Isaac Rosenberg in a trilby hat. Self-portrait, 1914.
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Walter H. Thompson (in trilby and pin-striped suit) stands on Churchill's left in June 1941. Churchill himself is wearing a Homburg.
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A trilby hat (or simply trilby) is a soft felt men's hat with a deeply indented crown, and a pinch at the front. The brim is narrow and often sharply upturned at the back. Traditionally it was made from rabbit hair felt, but is now sometimes made from other materials, including tweed and wool. Trilbies are softer than Homburgs, and have a flexible brim instead of a curved one. Trilbies are similar to fedoras, which can be seen as an American version with a wider brim. The hat's name derives from the stage adaptation of George du Maurier's 1894 novel Trilby; a hat of this style was worn in the first London production of the play, and promptly came to be called 'a Trilby hat'.
They were widely worn from the late 1920s onwards, initially as a casual sporting hat, such as for wearing to horse races. By the end of World War II, it had largely supplanted other hats such as Homburgs and bowlers for wear with a suit or smart casual, although it never replaced flat caps. It continued to be commonly worn this way until hats stopped being everyday wear for men in about the mid 1960s. The hat has been associated with jazz, ska and soul musicians, as well as members of the indie, rude boy, mod, skinhead and 2 Tone subcultures.
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