Etymology
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pillbox (n.)
also pill-box, "box for holding pills," 1730, from pill (n.) + box (n.). As a small round concrete machine gun nest, it came into use in World War I. As a type of hat, attested from 1958.
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fedora (n.)

type of hat, 1887, American English, from "Fédora," a popular play by Victorien Sardou (1831-1908) that opened 1882, in which the heroine, a Russian princess named Fédora Romanoff, originally was performed by Sarah Bernhardt. During the play, Bernhardt, a notorious cross-dresser, wore a center-creased, soft brimmed hat. Women's-rights activists adopted the fashion. The proper name is Russian fem. of Fedor, from Greek Theodoros, literally "gift of god," from theos "god" (from PIE root *dhes-, forming words for religious concepts) + dōron "gift" (from PIE root *do- "to give").

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blockhead (n.)
also block-head, "stupid person," 1540s (implied in blockheaded), from block (n.1) + head (n.); probably originally an image of the head-shaped oaken block used by hat-makers, though the insulting sense is equally old.
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pompom (n.)

"ornamental round tuft" (originally on a hat, etc.), 1897, an alteration of pompon "ornamental tuft; tuft-like flower head" (1748, pong-pong),  from French pompon (1725), a word of unknown origin; perhaps related to Old French pompe "pomp."

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homburg (n.)
type of soft felt hat with a curled brim and a dented crown, 1894, from Homburg, resort town in Prussia, where it was first made. Introduced to England by Edward VII.
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cloche (n.)
type of bell-jar, 1882, from French cloche "bell, bell glass" (12c.), from Late Latin clocca "bell" (see clock (n.1)). As a type of women's hat, recorded from 1907, so called from its shape.
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slouch (n.)
1510s, "lazy man," variant of slouk (1560s), probably from a Scandinavian source, perhaps Old Norse slokr "lazy fellow," and related to slack (adj.) on the notion of "sagging, drooping." Meaning "stooping of the head and shoulders" first recorded 1725. Slouch hat, made of soft material, first attested 1764.
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chou (n.)

"fashionable knot in a woman's dress or hat," 1883; earlier "small, round, cream-filled pastry" (1706), from French chou, literally "cabbage" (12c.), from Latin caulis "cabbage," literally "stalk" (see cole (n.1)).

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busby (n.)
"type of tall fur hat worn by hussars on parade," 1807, earlier "a kind of bushy, tall wig" (1764), of unknown origin, though it is both a place name and a surname in England. Related: Busbied.
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redcap (n.)

also red-cap, "porter at a railroad station," 1914, American English, from red (adj.1) + cap (n.). Earlier it was the name of the goldfinch, a type of domestic hen, a long-toothed spectre in Scottish castles, and anyone who wears a red hat (1540s).

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