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.

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.

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“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.

A lady wears a mini football pitch on her head at the 2004 Royal Ascot.
A lady wears a mini football pitch on her head at the 2004 Royal Ascot.

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.

Gertrude Shilling, 1996

Gertrude Shilling at the 1996 Royal Ascot wearing a hat that resembles a shower.
Gertrude Shilling at the 1996 Royal Ascot.

Fashion designer Shilling sports a fascinator resembling a shower.

Milla Stanovic, 2005

YORK, ENGLAND - JUNE 16:  Milla Stanovic, wears a hat with the Olympic rings to promote the London 2012 Olympic bid on Ladies Day at York Racecourse on June 16, 2005 at York, England.  Today was the third day of The Royal Meeting which this year is being held at the Yorkshire track due to redevelopment at Ascot.  The meeting features some of the flat seasons best racing and displays of the finest fashions.  (Photo by Julian Herbert/Getty Images)
Milla Stanovic in 2005.

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

Anneka Tanaka-Svenska, 2011

ASCOT, ENGLAND - JUNE 14: Anneka Tanaka-Svenska wears a hat created by Louis Mariette on the opening day of Royal Ascot at Ascot Racecourse on June 14, 2011 in Ascot, England. The five-day meeting is one of the highlights of the horse racing calendar, with 2011 marking the 300th anniversary of the annual event. Horse racing has been held at the famous Berkshire course since 1711.  (Photo by Dan Kitwood/Getty Images)
Anneka Tanaka-Svenska wears a hat created by Louis Mariette in 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.

Most Over-the-Top Hats at the Central Park Conservancy Hat Luncheon

Street style at Frederick Law Olmstead Awards Luncheon 2024
Street style at Frederick Law Olmstead Awards Luncheon 2024
Street style at Frederick Law Olmstead Awards Luncheon 2024
Street style at Frederick Law Olmstead Awards Luncheon 2024
Street style at Frederick Law Olmstead Awards Luncheon 2024
Street style at Frederick Law Olmstead Awards Luncheon 2024

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Launch Gallery: Most Over-the-Top Hats From the Royal Ascot Races Through the Years

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