Style & BeautyKentucky Derby

Photos Of The Wildest Hats The Kentucky Derby Has Ever Seen

Flamingos and horses and feathers, oh my!
By 

and

Photo Editor, HuffPost

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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:

Jamie Squire via Getty Images
A race fan at the derby at Churchill Downs on May 3, 2008.
Eclipse Sportswire via Getty Images
A woman wears a massive hat on May 6, 2017.
Jamie Rhodes / Reuters
Tony Offlutt of New Albany, Indiana, wears a huge derby-themed hat at Churchill Downs on May 4, 2002.
Chris Graythen via Getty Images
A woman wearing a festive hat at the derby on May 2, 2015.
Molly Riley / Reuters
A race fan displays her hat before the derby on May 3, 2008.
Getty Images
Former ice skaters Tara Lipinski and Johnny Weir arrive on the red carpet before the Kentucky Derby in 2014.
Dylan Buell via Getty Images
A race fan wearing a festive hat looks on from the infield prior to the derby on May 3, 2014.
Jeff Haynes / Reuters
A woman wears a fancy hat at the derby on May 5, 2012.
Reuters Photographer / Reuters
A race fan on May 3, 2008.
Jamey Price via Getty Images
A race attendee on May 4, 2013.
AI Project / Reuters
A patron wears a decorated derby hat before the derby in 2016.
Reuters Photographer / Reuters
A race fan displays her hat on May 3, 2008.
Dylan Buell via Getty Images
Tami Purcell of Knoxville, Tennessee, wearing a festive hat at the derby on May 3, 2014.
Reuters Photographer / Reuters
A race fan drinks a beer as he wears a horse hat before the 2008 derby.
JEFF HAYNES via Getty Images
Brittney Graham wears her personally designed derby hat on May 5, 2007.
Eclipse Sportswire via Getty Images
A woman wears a massive hat on at the 2017 derby.
Jeff Snyder via Getty Images
A derby hat from 2004.
ROBERT SULLIVAN via Getty Images
The classic mint julep glass sits atop a derby hat worn by a race fan in 2005.
ROBERT SULLIVAN via Getty Images
Derby fan George pictured in 2005. He had worn the same derby hat for 24 years.
Jamie Squire via Getty Images
A race fan in 2008.
Andy Lyons via Getty Images
A woman wearing a festive hat looks at the 2015 derby.
TIMOTHY A. CLARY via Getty Images
Col. Charles Matasich (left) and George Holter (right), wearing two of the most photographed hats at the 1997 Kentucky Derby.
Gregory Shamus via Getty Images
A woman wearing a festive hat looks on ahead of the 2017 derby.
Jeff Haynes / Reuters
A woman wears a fancy hat at the 2012 derby.
Icon Sportswire via Getty Images
A woman watches preliminary races before the 2017 derby.
USA Today Sports / Reuters
A patron wears a derby hat at the 2017 Kentucky Oaks race, which takes place at Churchill Downs the day before the Kentucky Derby.

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