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7 History-Making Hats, From the Pillbox to the Fedora

“A person carries off the hat,” leading milliner Philip Treacy (who’s made hats for British royals, Lady Gaga, and Kate Moss) once said. Whether it’s a topper adopted by the average person or a custom piece worn by a celebrity, a hat reflects personality, style, and practicality. Here are seven popular hats that have become linked to their most famous wearers.

Jackie Kennedy’s Pillbox Hat

Jacqueline Kennedy Wearing Pillbox Hat
Credit: Bettmann via Getty Images

Small, round, and rigid, usually with a flat or slightly rounded top, the pillbox hat emerged on American women’s heads sometime in the early 20th century, but First Lady Jackie Kennedy made them her own. During John F. Kennedy’s 1960 presidential campaign, she wore a white pillbox by Givenchy in front of a crowd of 2 million people. She later sported pillboxes by Halston, Oleg Cassini, and other American designers, and established a new and modern look for mid-century America. The whereabouts of the pink pillbox she wore when her husband was assassinated in 1963 — an indelible hat in American memory — are unknown.

George Washington’s Tricorn Hat

Painting of George Washington riding a horse.
Credit: Heritage Art/ Heritage Images via Getty Images

Whether or not you stuck a feather in it and called it macaroni, the tricorn hat was a staple on patriots’ heads during the American Revolution. The three-cornered, low-crowned hat grew out of the habit of military officers pinning up (or “cocking”) their broad-brimmed hats on three sides to funnel rain away. They became de rigueur for fashionable men in the late 17th and 18th centuries in Europe and the American colonies. The tricorn was usually worn with one point forward and often decorated with lace, braids, or feathers. George Washington wasn’t the only revolutionary to don one, but he was likely the most recognizable among his countrymen.

Napoleon’s Bicorne Hat

Statue of Napoleon Bonaparte.
Credit: Evannovostro/ Shutterstock

A close relative of the tricorn hat was the bicorne hat — a broad-brimmed, low-crowned hat cocked on two sides. Most military personnel in the 18th century wore one of the corners forward, but Napoleon sported the pinned side to the front, believing that it made him appear approachable. One of the most reproduced portraits of the general, Jacques-Louis David’s Napoleon Crossing the Alps, depicts him wearing his signature chapeau. Napoleon remains so identified with the style that several of his bircornes have sold at auction for stratospheric prices. The one he is believed to have worn during his successful 1807 campaign sold for $1.4 million in September 2021.

Abraham Lincoln’s Top Hat

President Abraham Lincoln, flanked by civil war officials, standing outside of a tent, 1863.
Credit: Smith Collection/ Gado via Getty Images

As tricorn hats fell out of fashion, the top hat took over. Championed by Regency dandy Beau Brummel, a confidante of the future George IV, top hats were tall, flat-topped, narrow-brimmed, and originally made of beaver felt; they were possibly modeled on the 17th-century capotain or “Pilgrim hat.” Silk top hats became more common by the mid-19th century and were worn by all respectable Victorian men. Abraham Lincoln was not alone in wearing top hats to public events, but at 6 feet and 4 inches tall, plus an 8-inch hat, he really stood out in a crowd. The top hat Lincoln was wearing when he was assassinated at Ford’s Theatre is one of the Smithsonian’s most treasured artifacts.

Davy Crockett’s Coonskin Cap

Painting showing men fighting the Battle of the Alamo with Davey Crocket in the foreground
Credit: Ed Vebell via Getty Images

David Crockett — military scout, Tennessee politician, and member of Congress — had a talent for spinning tales about his experiences as a frontiersman. Following his death at Texas’s Alamo in 1836, numerous books, plays, and pamphlets embellished his skills as a fearless hunter and sharpshooter in a raccoon-skin cap. Whether Crockett ever wore one is debatable. But when Disney released the 1955 live-action film Davy Crockett, King of the Wild Frontier, starring Fess Parker in a coonskin cap, American boys went bananas for the rustic toppers. At the height of Crockettmania, stores sold about 5,000 faux-fur coonskin caps a day.

Al Capone’s Fedora Hat

Al Capone seated facing Captain John Stege of the Chicago Police Department
Credit: Chicago Sun-Times/ Chicago Daily News collection/ Chicago History Museum via Getty Images

Fedoras emerged in the 1880s, possibly based on an earlier Alpine design of soft felt with a center crease and a pinch at the front. Its debut closely followed the premiere of Victorien Sardou’s play Fédora, and the name got attached to the hat. But fedoras really entered the style pages in the 1920s, when flashy gangsters like Al Capone were rarely pictured without them in newspapers and newsreels. Fedora fans copied Capone’s habit of wearing them tilted on his head. Even after Prohibition ended in 1933, the style remained associated with tough guys and shady types in novels by Raymond Chandler and film noir pictures.

Winston Churchill’s Homburg Hat

Winston Churchill walking in the street.
Credit: H. F. Davis/ Topical Press Agency via Getty Images

One of the many hat styles popularized by European royalty, the homburg originated in the German spa town of Bad Homburg in the 1880s. Some historians believe the form, with a single crease at the crown, a wide grosgrain band, and a flat brim with curled edges, was based on a traditional hunting hat from the region. The homburg gained worldwide attention when the Prince of Wales (later Edward VII) wore them, but the person most associated with homburgs is surely Winston Churchill. The British prime minister wore a gray homburg to the 1943 conference with President Franklin Roosevelt in Casablanca, where the two leaders hashed out a plan to end World War II. Churchill and the homburg remained linked in the public imagination thereafter.

Featured image credit: Allen.G/ Shutterstock