Winston Churchill acquired hundreds of hats of every kind during his lifetime.

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Winston Churchill had a larger-than-life personality, which was reflected in his unique fashion choices, including, on occasion, a velvet romper. Churchill was also known for his expansive hat collection, which numbered in the hundreds and wasn’t limited to just one style. In addition to the typical formal and casual hats of the time, the statesman boasted military, equestrian, and even trade headgear. As his son Randolph once said, “My father never met a hat he didn’t like.”

Hats became part of Churchill’s public image early on. After 1910, when a photographer snapped a photo of him in a too-small hat, political cartoons usually depicted the politician with little hats atop an outsized head. Rather than take offense, Churchill actively encouraged the caricature. A 1939 profile of Churchill in Life magazine featured 20 portraits of him throughout his life in some of his favorite hats, from a “schoolboy bowler” in his early 20s to an engineer’s cap in his early 60s.

Churchill’s many official government and academic posts came with even more hats to add to his collection, which he often continued wearing long after his tenure — including a formal bicorn hat with gold filigree for his position as Lord Warden of the Cinque Ports, a high military rank that comes with a castle. Later in his life, Churchill was most closely associated with Homburg hats, which he made famous during World War II.

In one popular anecdote, a house where Churchill was staying with a group of guests for his brother’s wedding caught fire, and soon after, Churchill was spotted wearing a brass firefighter’s helmet with his dressing gown, bossing the fire brigade around. Truly, he could find a hat for any occasion.

By the Numbers

Did you know?

Churchill was hit by a car in New York City.

Churchill was visiting the United States on a lecture circuit in 1931 when, during a stop in New York City, he set out to pay a visit to an old friend. He didn’t have the exact address, so he was lost and running late when he thought he saw his friend’s building across a busy road. (He was actually about half a mile from his destination.) In England, cars drive on the left side of the street (compared with the right in the United States), so Churchill looked in the wrong direction before crossing the street, and was hit by a fast-moving car. Churchill was rushed to a hospital, where he wrote a long article detailing the incident. He sold it to the Daily Mail for $2,500 and, newly flush with cash, made a full recovery in the Bahamas. Churchill harbored no hard feelings toward the driver, and even gave him an inscribed copy of his book My Early Life, which had been published the year before.