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A bowler hat, or derby, is a rounded felt hat commonly worn from the 1850s to the early-to-mid-1900s, especially in Victorian Britain and The Wild West. Bowler hats were once considered the national hat of England, and used to be associated with the upper-middle class there, especially with bankers, in the early half of the 20th century.
You can count on a character who wears a bowler hat to be refined (unless, say, he's a villain in a western). In fact, he might even wear a monocle to show his culturedness. The bowler hat hung on in the City of London into the 1960s. In the early 1960s, new recruits to some City law firms got an allowance for the purposes of buying a bowler.
Compare and contrast Dastardly Dapper Derby.
- Lucky the Leprechaun, the mascot for General Mills' Lucky Charms cereal, wears a green bowler with a shamrock stuck in it. While not evil, he is a trickster.
- The British bank Bradford & Bingley portrayed its two namesakes as bowler-hatted city gents. Eventually, its logo became a stylised version of the hat itself.
- Likewise there was a period when the symbol of the UK Inland Revenue was a stereotyped taxman in pinstripe suit and bowler.
- Rene Magritte frequently drew men wearing bowler hats. For instance, in "Golconda", the sky above a city street is full of them. They appear to symbolise anonymity, which is why Magritte also wore one in Real Life.
- Golden Age Green Lantern Sidekick Doiby Dickles is named after his hat.
- Richie Rich's butler, Cadbury, almost always wore a bowler hat in public.
- Bumbling look-a-like detectives Thompson and Thomson in Tintin
- Seamus McFly in Back to The Future Part 3.
- Curly of The Three Stooges always looked dapper in his "doiby".
- Lou Costello of Abbott and Costello
- Dr. Watson is often portrayed with a bowler hat, as the Quintessential British Gentleman.
- Cornelius Fudge, Minister of Magic from Harry Potter, was often described as having a lime green bowler.
- Sweyn embarrasses his brothers in The Great Brain Does It Again when he returns from high school back east wearing a derby hat along with a fancier, more grown-up, style suit than a boy his age would wear in Adenville.
- Mr. Steed of The Avengers is likely the Trope Codifier.
- Lord Bowler (so named for his hat) in The Adventures of Brisco County Jr was the Anti-Hero to Brisco's hero.
- The Czechoslovakian character Pan Tau usually wore a magic Bowler Hat.
- In the TV adaptation of Jeeves and Wooster, Jeeves' hat of choice is bowler hat.
- Monty Python's Flying Circus often used these as indicative of bankers and accountants.
- Chap-hop star Mr. B The Gentleman Rhymer often sports a stylish derby.
- Mr Davenport, the Victorian-serial version of Dave in Narbonic, wears a bowler hat, and considers himself a gentleman.
- Baron von Fogel of The League of STEAM wears one.
- Homsar from Homestar Runner wears one, but he is more demented than dashing. Whenever he speaks, his bowler hat will actually fly off his head for a while until he stops talking.
- Sir Winston Churchill
- Charlie Chaplin
- Stan Laurel and Oliver Hardy
- Styme of The Little Rascals got his trademark derby from Stan himself, who had taken a liking to him.