Hats and Fashion of the 2019 Kentucky Derby

Break out the feathers and sinamay. The stands of Churchill Downs will once again play host not only to some of the fastest Thoroughbreds in the world, but also to a bevy of the most over-the-top headwear made. From the wildly extravagant to the small but simple fascinators, see this year's Derby fashion in photos.

26 photos
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A woman wears a ribboned fascinator at the 145th running of the 145th Kentucky Derby.
John Minchillo/AP
A woman wears a ribboned fascinator at the 145th running of the 145th Kentucky Derby.
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A man wears a hat festooned with red roses before the 145th running of the 145th Kentucky Derby. The first race of the Triple Crown is known colloquially as the "Run for the Roses."
John Minchillo/AP
A man wears a hat festooned with red roses before the 145th running of the 145th Kentucky Derby. The first race of the Triple Crown is known colloquially as the "Run for the Roses."
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A woman wears a feathered hat during the 145th running of the 145th Kentucky Derby.
John Minchillo/AP
A woman wears a feathered hat during the 145th running of the 145th Kentucky Derby.
4/26
A woman wears a blue rose fascinator during the 145th running of the 145th Kentucky Derby.
John Minchillo/AP
A woman wears a blue rose fascinator during the 145th running of the 145th Kentucky Derby.
5/26
A woman wearing a blue straw hat looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Andy Lyons/Getty Images
A woman wearing a blue straw hat looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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A woman wearing a festive fascinator looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Andy Lyons/Getty Images
A woman wearing a festive fascinator looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Why just drink a mint julep when you can wear it? Megan Huckaby of Woodford Reserve attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Loccisano/Getty Images for Churchill Downs
Why just drink a mint julep when you can wear it? Megan Huckaby of Woodford Reserve attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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A guest dressed to impress attend the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Jason Kempin/Getty Images for Churchill Downs
A guest dressed to impress attend the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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A woman wears a mesh fascinator to the 145th running of the Kentucky Derby at Churchill Downs on May 04, 2019 in Louisville, Kentucky.
Tom Pennington/Getty Images
A woman wears a mesh fascinator to the 145th running of the Kentucky Derby at Churchill Downs on May 04, 2019 in Louisville, Kentucky.
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Even the men are wearing their own festive headwear for the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Andy Lyons/Getty Images
Even the men are wearing their own festive headwear for the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Who said Derby hats can't be fun?
Tom Pennington/Getty Images
Who said Derby hats can't be fun?
12/26
A woman wears a sinamay fascinator prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Tom Pennington/Getty Images
A woman wears a sinamay fascinator prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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A woman in a hat adorned with a giant rose poses prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Jamie Squire/Getty Images
A woman in a hat adorned with a giant rose poses prior to the 145th running of the Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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LOUISVILLE, KENTUCKY - MAY 04: A woman wearing a festive hat looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 04, 2019 in Louisville, Kentucky. (Photo by Michael Reaves/Getty Images)
LOUISVILLE, KENTUCKY - MAY 04: A woman wearing a festive hat looks on prior to the 145th running of the Kentucky Derby at Churchill Downs on May 04, 2019 in Louisville, Kentucky. (Photo by Michael Reaves/Getty Images)
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A guest wearing a peacock trimmed fascinator attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Robin Marchant/Getty Images for Churchill Downs
A guest wearing a peacock trimmed fascinator attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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LOUISVILLE, KENTUCKY - MAY 04: Guests attend the Louisville Healthcare CEO Council Kentucky Derby Green Room during the 145th Kentucky Derby at Churchill Downs on May 04, 2019 in Louisville, Kentucky. (Photo by Michael Hickey/Getty Images for Louisville Healthcare CEO Council)
Getty Images for Louisville Heal
LOUISVILLE, KENTUCKY - MAY 04: Guests attend the Louisville Healthcare CEO Council Kentucky Derby Green Room during the 145th Kentucky Derby at Churchill Downs on May 04, 2019 in Louisville, Kentucky. (Photo by Michael Hickey/Getty Images for Louisville Healthcare CEO Council)
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Katie Bouchard and Joanna Clark wear fascinators to the Kentucky Derby Green Room during the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Hickey/Getty Images for Louisville Heal
Katie Bouchard and Joanna Clark wear fascinators to the Kentucky Derby Green Room during the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Guests attend the Kentucky Derby Green Room during the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Hickey/Getty Images for Louisville Heal
Guests attend the Kentucky Derby Green Room during the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Joey Wagner (R) attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Jason Kempin/Getty Images for Churchill Downs
Joey Wagner (R) attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Connie Orlando attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Loccisano/Getty Images for Churchill Downs
Connie Orlando attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Cassandra Jean attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Loccisano/Getty Images for Churchill Downs
Cassandra Jean attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Star Jones attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Loccisano/Getty Images for Churchill Downs
Star Jones attends the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Guests wearing wide-brimmed fascinators attend the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Jason Kempin/Getty Images for Churchill Downs
Guests wearing wide-brimmed fascinators attend the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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Guests in matching outfits and fascinators attend the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Michael Loccisano/Getty Images for Churchill Downs
Guests in matching outfits and fascinators attend the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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It's spring for this guest at the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
Robin Marchant/Getty Images for Churchill Downs
It's spring for this guest at the 145th Kentucky Derby at Churchill Downs on May 4, 2019, in Louisville, Kentucky.
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A guest attends the 145th Kentucky Derby at Churchill Downs wearing a pink magnolia-theme fascinator with matching outfit on May 4, 2019, in Louisville, Kentucky.
Robin Marchant/Getty Images for Churchill Downs
A guest attends the 145th Kentucky Derby at Churchill Downs wearing a pink magnolia-theme fascinator with matching outfit on May 4, 2019, in Louisville, Kentucky.
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