The Kentucky Derby and fancy hats go together like Carrie Bradshaw and a pair of Manolo Blahniks.
Fashion has played a major role in the Louisville event since its inception in 1875. Women would coordinate all aspects of their outfits, from their hats and dresses to their bags and parasols, according to Ellen Goldstein, a professor at the Fashion Institute of Technology who spoke to NBC Connecticut about the derby in 2013.
“To go to a horse racing event was really a regal affair,” she said. “It was just as important as going to a cocktail party, or a ball.”
Over the years, though, it’s the hats that have really caught our attention. Women and men go all out with their derby headwear, sporting everything from flamingos to horses and bundles of flowers atop their heads.
Below, check out some of the wildest hats the Kentucky Derby has ever seen:
A race fan at the derby at Churchill Downs on May 3, 2008.
A woman wears a massive hat on May 6, 2017.
Tony Offlutt of New Albany, Indiana, wears a huge derby-themed hat at Churchill Downs on May 4, 2002.
A woman wearing a festive hat at the derby on May 2, 2015.
A race fan displays her hat before the derby on May 3, 2008.
Former ice skaters Tara Lipinski and Johnny Weir arrive on the red carpet before the Kentucky Derby in 2014.
A race fan wearing a festive hat looks on from the infield prior to the derby on May 3, 2014.
A woman wears a fancy hat at the derby on May 5, 2012.
A race fan on May 3, 2008.
A race attendee on May 4, 2013.
A patron wears a decorated derby hat before the derby in 2016.
A race fan displays her hat on May 3, 2008.
Tami Purcell of Knoxville, Tennessee, wearing a festive hat at the derby on May 3, 2014.
A race fan drinks a beer as he wears a horse hat before the 2008 derby.
Brittney Graham wears her personally designed derby hat on May 5, 2007.
A woman wears a massive hat on at the 2017 derby.
A derby hat from 2004.
The classic mint julep glass sits atop a derby hat worn by a race fan in 2005.
Derby fan George pictured in 2005. He had worn the same derby hat for 24 years.
A race fan in 2008.
A woman wearing a festive hat looks at the 2015 derby.
Col. Charles Matasich (left) and George Holter (right), wearing two of the most photographed hats at the 1997 Kentucky Derby.
A woman wearing a festive hat looks on ahead of the 2017 derby.
A woman wears a fancy hat at the 2012 derby.
A woman watches preliminary races before the 2017 derby.
A patron wears a derby hat at the 2017 Kentucky Oaks race, which takes place at Churchill Downs the day before the Kentucky Derby.
The Duchess of York, later Queen Mary, with her children Prince Edward, later the Duke of Windsor (right), and Prince Albert, later King George VI, in 1906.
The Duke of Kent, younger son of King George V and Queen Mary, at Epsom races for the Derby stakes on May 24, 1939. He is with his wife, Marina, Duchess of Kent, who was the daughter of Prince Nicholas of Greece.
Princess Anne at Horse Trials with members of the Royal Canadian Mounted Police in the U.K., 1968.
Princess Anne At The Great Children's Party In Hyde Park, London, 1979.
Princess Diana greets people in Wales, 1981.
Diana, Princess of Wales, during a visit to Guildford Cathedral on Dec. 21, 1981.
Diana, Princess of Wales, visits University College Hospital in London in December 1982. She wears a John Boyd hat and a velvet suit by Caroline Charles.
Sarah, Duchess of York, and Princess Margaret attend Ascot in 1987.
Sarah, Duchess of York, wears a large blue and white hat during a visit to Fort Edmonton, Canada, in July 1987.
Queen Elizabeth II and the Queen Mother at All Saints Church in Windsor, 1987.
Princess Beatrice of York rides in the carriage procession at Trooping the Colour on June 16, 2007, in London.
Princess Beatrice attends the wedding of Peter Phillips to Autumn Kelly at St. George's Chapel in Windsor on May 17, 2008.
Kate Middleton attends the wedding of Lady Rose Windsor and George Gilman at The Queen's Chapel, St. James' Palace, on July 19, 2008, in London.
The future Duchess of Cambridge at the Naming Ceremony and Service of Dedication for the Atlantic 85 Lifeboat "Hereford Endeavour" at Trearddur Bay Lifeboat Station at Anglesey on Feb. 24, 2011, in Bangor, Wales.
Sophie Winkleman, Lady Frederick Windsor, exits following the marriage of Prince William, Duke of Cambridge, and Catherine, Duchess of Cambridge, at Westminster Abbey on April 29, 2011, in London.
Princess Beatrice leaves Westminster Abbey following the marriage of the Duke and Duchess of Cambridge on April 29, 2011.
Princess Eugenie of York leaves Westminster Abbey following the marriage of the Duke and Duchess of Cambridge on April 29, 2011.
Camilla, Duchess of Cornwall, and Catherine, Duchess of Cambridge, travel down The Mall in a horse-drawn carriage as they attend the Trooping the Color parade on June 11, 2011, in London.
The Duchess of Cambridge leaves Canongate Kirk on the afternoon of the wedding of Mike Tindall and Zara Philips on July 30, 2011, in Edinburgh, Scotland.
The Duchess of Cambridge visits the Canadian Museum of Civilization to attend a citizenship ceremony on July 1, 2011, in Gatineau, Canada.
The Duchess of Cambridge on board the Royal Barge "Spirit of Chartwell" during the Diamond Jubilee Thames River Pageant on June 3, 2012, in London.
The Duchess of Cambridge travels in a horse-drawn carriage down The Mall during the annual Trooping the Color ceremony on June 16, 2012, in London.
The Duchess of Cambridge and Queen Elizabeth II smile as they visit Vernon Park during a Diamond Jubilee visit to Nottingham on June 13, 2012.
Camilla, Duchess of Cornwall, attends the Commonwealth Observance Service at Westminster Abbey on March 10, 2014, in London.
Camilla, Duchess of Cornwall, leaves a memorial service for Sir David Frost at Westminster Abbey on March 13, 2014, in London.
Camilla, Duchess of Cornwall, and Catherine, Duchess of Cambridge, travel down The Mall in a horse-drawn carriage during Queen Elizabeth II's Birthday Parade on June 14, 2014, in London.
Catherine, Duchess of Cambridge, arrives by carriage at Royal Ascot on June 20, 2017, in Ascot, England.
Queen Elizabeth II visits HMS Sutherland on Oct. 23, 2017, at London's West India Dock as the ship celebrates the 20th anniversary of her commissioning it.
Queen Elizabeth II attends the traditional Easter Sunday service at St. George's Chapel, Windsor Castle, on April 1, 2018.
Anne, Princess Royal, attends the 2018 Commonwealth Day service at Westminster Abbey on March 12, 2018, in London.
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