The Most Over-the-top Hats From the Royal Ascot Races Through the Years

Attended by the likes of Kate Middleton, King Charles, Queen Camilla, Princess Anne, Zara Tindall, to name a few, the Royal Ascot racing event is a chance for attendees to watch horses — and each other.

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The Royal Enclosure, held annually at the Ascot Racecourse, features a strict dress code. All women must wear hats and, in most cases, skirts or dresses to the knee, while men must wear top hats and morning suits.

“Although there are longstanding dress codes to follow, there’s a real sense of creativity where people can experiment with styles they may not wear in their day-to-day lives,” Daniel Fletcher, who was named the first creative director in the event’s 313-year history for the 2024 season , previously told WWD.

Due to the strict dress code, hats have become a key form of expression for the event’s guests. From 1982 to the present day, outrageous hats have ranged from Gertrude Shilling’s shower-inspired affair to one guest’s recreation of a football pitch.

Founded by Queen Anne in 1711, the Royal Ascot Races have since become a fixture for the British royal family to attend as a unit.

The late monarch Queen Elizabeth II was an avid hippophile, while her daughters-in-law, the late Princess Diana and Sarah Ferguson; and Catherine Middleton and Meghan Markle, the wives of Prince William and Prince Harry, respectively, have always captured the attention of the press for what they wear.

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Gertrude Shilling, 1996

Fashion designer Shilling sports a fascinator resembling a shower.

Milla Stanovic, 2005

Racegoer Stanovic promoted the London 2012 Olympic bid in style, in a hat fashioned after the Games’ rings.

Anneka Tanaka-Svenska, 2011

The British presenter wore a sky-high hat that paid homage to Marie Antoinette.

See more over-the-top hats in the gallery below.

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