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Throughout the ages, hats have been more than just a fashion accessory—they've served as symbols of status, political expression, or simply a mark of personal style. Some hats have become so closely associated with a particular individual that they are instantly recognized, often becoming the go-to choice for anyone dressing as that figure at a costume event. Below are eight of the most iconic hats in history and the figures who made them famous.
1. WINSTON CHURCHILL'S HOMBURG
Winston Churchill, the British prime minister during World War II, was famous for his love of hats. He even wrote a witty essay on the subject, noting that unlike other prominent leaders, he didn’t have a signature hairstyle, glasses, or facial hair for artists to focus on. Instead, his iconic hats became the focal point for caricaturists and photographers of the era.
Churchill was known for wearing various hat styles, from top hats to bowler hats, but he is best remembered for his homburg. The homburg is a felt hat with a curved brim, a crease running from front to back, and a grosgrain ribbon as a band. It became popular in Britain through Prince Edward VII, who first encountered it during a visit to Bad Homburg in Germany in the 1880s. Churchill owned several homburgs, including a classic black one and a stylish pale gray version with a black ribbon. In 1991, one of his favorites, embossed with his initials in gold, sold at auction for $11,750.
2. NAPOLEON'S BICORNE
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Napoleon Bonaparte, the French emperor, was a master of using imagery and attire to assert his power and influence. His most iconic headwear was his black felt bicorne made from beaver fur.
The bicorne, with its distinctive deep crease and pointed corners, was traditionally worn with the points at the front and back. However, to stand out on the battlefield, Napoleon wore it sideways, making it instantly recognizable to those observing him. He always had his hats crafted by Poupart & Cie, ordering four new ones each year. Napoleon reportedly disliked the look of a brand-new hat and had his valets break them in for him.
In 2014, a highly anticipated auction of Napoleon memorabilia took place in France, with the standout item being the bicorne hat that Napoleon is believed to have worn during the Battle of Marengo in 1800. Although Napoleon owned at least 120 hats, historians now believe that only 19 examples remain, most of which are kept in museums or private collections. This rarity ensured that the auction of one of Napoleon's hats would be a major event, and it came as no surprise when the iconic bicorne sold for a staggering $2.4 million.
3. ST. THOMAS MORE'S BONNET
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Thomas More, the Lord High Chancellor of England under Henry VIII, was renowned as a Catholic scholar. However, after his refusal to recognize Henry VIII as the head of the Church of England, he was convicted of treason and executed in 1535. Later canonized as a saint by the Catholic Church, More’s belongings, including his famous bonnet, have become cherished relics. His black velvet Tudor bonnet is immortalized in the renowned portrait by Hans Holbein. At President Obama’s 2013 inauguration, all eyes were on Justice Antonin Scalia, who wore a replica of More’s bonnet, a gift from the Thomas More Society—once again demonstrating the enduring power of a remarkable hat. In September 2016, St. Thomas More's original bonnet was put on display at the St. John Paul II National Shrine in Washington, D.C., alongside other relics, including a fragment of jawbone and a tooth.
4. ABRAHAM LINCOLN'S STOVEPIPE
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Abraham Lincoln, the 16th president of the United States, stood an impressive 6 feet 4 inches tall, and his signature top hat only emphasized his towering height. Lincoln often used his hat as a storage place, tucking speeches and important papers inside it, making the hat not only a stylish accessory but also a practical storage solution.
The most iconic of Lincoln’s stovepipe hats was the very one he wore the night he was assassinated at Ford's Theater on April 14, 1865. The silk hat, purchased from Washington hatmaker J. Y. Davis, featured two ribbons—one thin black ribbon with a small buckle and a 3-inch black grosgrain mourning ribbon, which Lincoln likely added himself in memory of his son, Willie. The hat was left on the floor beside his seat during the performance and remained there after the assassination. Both the chair Lincoln sat in and the hat were quickly collected by the War Department as evidence for the trial of John Wilkes Booth and later given to the Smithsonian Institution, where it was stored carefully. In 1893, the hat was put on public display as part of an exhibition organized by the Lincoln Memorial Association. Today, it remains one of the Smithsonian’s most valuable artifacts, offering a direct connection to one of America’s most revered leaders.
5. DAVY CROCKETT'S COONSKIN CAP
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Coonskin caps are fur hats made from raccoon pelts, with the tail of the animal hanging down the back. Originally worn by Native Americans, these hats were later adopted by 18th-century frontiersmen as hunting gear. Davy Crockett, often shown wearing a coonskin cap, is closely linked to the iconic accessory. When Crockett left his political career and returned to Texas, where he ultimately perished at the Alamo, witnesses recalled seeing him with his coonskin cap. One such witness, Susanna Dickinson, a survivor of the Alamo massacre, later described seeing Crockett’s body: "I recognized Col. Crockett lying dead and mutilated between the church and the two-story barrack building, and even remember seeing his peculiar cap lying by his side." Though historians debate the accuracy of this recollection, it emphasizes the strong connection between Crockett and his beloved coonskin hat.
6. JACKIE KENNEDY'S PILLBOX
Cecil W. Stoughton via Wikimedia // Public Domain
Jackie Kennedy remains one of America's most iconic style figures, and one of her most memorable looks was the pillbox hat she often wore, perched elegantly atop her head. Kennedy had several versions of the pillbox, but the most famous is the watermelon pink one she wore with a matching pink Chanel-style suit on November 22, 1963, the day President John F. Kennedy was assassinated. Jackie, dressed in her pink suit, was covered in her husband's blood. Despite repeated suggestions from aides to change her clothes, Jackie reportedly refused, telling biographer William Manchester, "No, let them see what they've done." When Jackie eventually discarded the pink suit, it was preserved at the National Archives in Maryland, where it will remain until at least 2103, as displaying the bloodstained garment is considered too distressing. As for the hat, it is known that during her visit to Parkland Hospital, where JFK’s body was taken, Jackie removed the pillbox hat and handed it to her private secretary, Mary Gallagher—but what happened to it afterward remains a mystery.
7. GUY FAWKES'S SUGARLOAF
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A contemporary engraving by Crispijn van de Passe (the Elder) gives us a lasting image of the Gunpowder Plot conspirators, all wearing their distinct sugarloaf hats. The most infamous of the plotters, Guy Fawkes, has since become a notorious figure in British folklore. Every November 5, effigies of Fawkes are burned on bonfires, and fireworks fill the sky, commemorating the failed plot to blow up the Houses of Parliament.
The sugarloaf hat gained popularity during the Stuart Period (1603–1714) in British history, with its pointed crown resembling the sugar loaves imported from the New World. The hat became associated with Parliamentarian anti-monarchists during the English Civil War (1642–51), serving as a contrast to the ornate cavalier hats worn by the royalists. Historians suggest that the sugarloaf hat might have symbolized rebellion: it was customary in the 1600s to remove one’s hat when a superior entered a room, yet those who wore the sugarloaf hat would defiantly keep it on in the presence of aristocrats.
Following the failure of the Gunpowder Plot, the conspirators met their end, but the image of Guy Fawkes in his sugarloaf hat endured. To this day, similar hats are placed on effigies of Fawkes, which are then burned on bonfires across Britain each November 5.
8. THEODORE ROOSEVELT'S PANAMA HAT
A photograph of Roosevelt sitting on a steam shovel at the Panama Canal. Image credit: Wikimedia // Public Domain
On November 16, 1906, President Theodore Roosevelt was captured in a famous photograph during his inspection of the Panama Canal construction. In the image, Roosevelt is at the helm of a massive steam-shovel, wearing a stylish light straw hat with a black band. The press quickly dubbed this hat his "Panama" hat.
Although known as the Panama hat today, this style is actually traditionally crafted in Ecuador, where the native toquilla palm plant is used to weave it. Ecuadorian artisans have been weaving these hats since the time of the Incas, but in the 1850s, as travelers passed through Panama on their way to the United States for the gold rush, Ecuadorian hat vendors began exporting their hats to Panama. The popularity of the hats surged during the Panama Canal construction, as the lightweight design provided perfect sun protection for the workers. When Roosevelt’s photograph wearing the hat was published in newspapers like The New York Times, the hat became a nationwide fashion trend, and the Ecuadorian sombreros de paja toquilla were forever rebranded as the Panama hat.
