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50-plus photos of Kentucky Derby hats through the years
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Spotlight

50-plus photos of Kentucky Derby hats through the years

  • The Associated Press
  • Apr 29, 2021
  • Apr 29, 2021 Updated Nov 6, 2022
  • 0

The Kentucky Derby is back on the first Saturday in May — and so are the hats. Here's a look at some of the best (and biggest) over the years.

Arcaro Jones Wright

Jockey Eddie Arcaro is kissed by his mother, Josephine, holding roses, after winning the Kentucky Derby at Churchill Downs, Louisville, Ky., on May 3, 1952. Arcaro, who was riding Hill Gail, celebrates his fifth Derby win. At left is Lucille Parker Wright, whose racing stable Calumet Farm has had five Derby winners. At center is Ben Jones, who has trained all six Derby winners. (AP Photo)

ASSOCIATED PRESS
Princess Margaret

Britain’s Princess Margaret, smokes cigarette while watching races at Churchill Downs in Louisville, Kentucky on May 4, 1974. The princess is in Louisville to view the Kentucky Derby. (AP Photo)

AP Photo
Pat Valenzuela Kentucky Derby 1989

Jockey Pat Valenzuela gets a kiss from Mrs. Peggy Whittingham, wife of trainer Charlie Whittingham, after riding Sunday Silence to a win in the Kentucky Derby Sunday, May 8, 1989 at Churchill Downs in Louisville, KY. Looking on is Valenzuela's wife Jeana. (AP Photo/Ed Reinke)

Ed Reinke
KENTUCKY DERBY

Horse racing fans sporting their Kentucky Derby hats gaze down at the paddock from the balcony of the new grandstand at Churchill Downs, Saturday morning, May 7, 2005, in Louisville, Ky. The 131st Kentucky Derby is the 10th race of the day. (AP Photo/Timothy D. Easely)

TIMOTHY D. EASLEY
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/Darron Cummings)

Darron Cummings
Kentucky Derby Horse Racing

Sandy Dompkosky, wearing a Tiz the Law, themed hat stands in the paddock before the 146th running of the Kentucky Derby at Churchill Downs, Saturday, Sept. 5, 2020, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
APTOPIX Kentucky Derby Horse Racing

A woman wears a hat before the 144th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 5, 2018, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
2019 Kentucky Derby

A female fan in a fancy hat is seen at Churchill Downs Wednesday, May 1, 2019, in Louisville, Ky. The 145th running of the Kentucky Derby is scheduled for Saturday, May 4. (AP Photo/Gregory Payan)

Gregory Payan
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
Kentucky Derby Horse Racing

A woman wears a hat during the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat during the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat during the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat during the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat during the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A man wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
Kentucky Derby Horse Racing

A woman wears a hat before the 145th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 4, 2019, in Louisville, Ky. (AP Photo/John Minchillo)

John Minchillo
KENTUCKY DERBY

Tammy poole, of Louisville, Ky., wears her pink Kentucky Derby hat during Derby day festivities at Churchill Downs, Saturday, May 7, 2005, in Louisville, Ky. The 131st Kentucky Derby is the 10th race of the day. (AP Photo/james Crisp)

JAMES CRISP
KENTUCKY DERBY

Horse racing fan George Holter, from Prairie Village, Kan., wears his twin spires Kentucky Derby hat as he walks through the paddock area at Churchill Downs, Saturday, May 7, 2005, in Louisville, Ky. Holter is attending his 26th derby. (AP Photo/Darron Cummings)

DARRON CUMMINGS
KENTUCKY DERBY

Skip Koepnick, of Wyoming, Mich., sports his Kentucky Derby hat at Churchill Downs, Saturday, May 7, 2005, in Louisville, Ky. The 131st Kentucky Derby is the 10th race of the day. (AP Photo/Brian Bohannon)

BRIAN BOHANNON
KENTUCKY DERBY

Ernie Trent, of Jeffersonville, Ind., sports his twin spires hat during Kentucky Derby day festivities at Churchill Downs, Saturday, May 7, 2005, in Louisville, Ky. The 131st Kentucky Derby is the 10th race of the day.(AP Photo/ Brian Bohannon)

BRIAN BOHANNON
Kentucky Derby Horse Racing

Jenny Hollifield, left, and Banita Conte wear hats before the Kentucky Oaks race at Churchill Downs Friday, May 1, 2009, in Louisville, Ky. (AP Photo/Morry Gash)

Morry Gash
Kentucky Derby Horse Racing

A spectator wears a fancy hat while waiting for the Kentucky Oaks at Churchill Downs Friday, May 1, 2009, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
Kentucky Derby Horse Racing

Charles Matasich or Proctorville, Ohio wears a hat before the 136th Kentucky Derby horse race at Churchill Downs Saturday, May 1, 2010, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
Kentucky Derby Horse Racing

Dana Settles wears a fancy hat during the 139th Kentucky Derby at Churchill Downs Saturday, May 4, 2013, in Louisville, Ky. (AP Photo/David Goldman)

David Goldman
Kentucky Derby Horse Racing

A spectator wear a hat the 133rd Kentucky Derby at Churchill Downs in Louisville, Ky., Saturday, May 5, 2007. (AP Photo/Charlie Riedel)

Charlie Riedel
Kentucky Derby Horse Racing

Patty Ethington of Shelbyville, Ky., smiles with her fancy hat at the 135th Kentucky Derby at Churchill Downs Saturday, May 2, 2009, in Louisville, Ky. (AP Photo/Patti Longmire)

Patti Longmire
Kentucky Derby Horse Racing

Jennifer Baisden of Columbus, Ohio, shows off her fancy hat at the 135th Kentucky Derby at Churchill Downs Saturday, May 2, 2009, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
Kentucky Derby Horse Racing

Spectators arrive with their fancy hats to attend the 139th Kentucky Derby at Churchill Downs Saturday, May 4, 2013, in Louisville, Ky. (AP Photo/Matt Slocum)

Matt Slocum
Kentucky Derby Horse Racing

A woman wears a hat during the 136th Kentucky Derby horse race at Churchill Downs Saturday, May 1, 2010, in Louisville, Ky. (AP Photo/Darron Cummings)

Darron Cummings
Kentucky Derby Horse Racing

Erica Harris of Omaha, Neb., wears a Derby hat before the 136th Kentucky Derby horse race at Churchill Downs Saturday, May 1, 2010, in Louisville, Ky. (AP Photo/Rob Carr)

Rob Carr
Kentucky Derby Horse Racing

A spectator shows off her Derby hat before the 137th Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2011, in Louisville, Ky. (AP Photo/Ed Reinke)

Ed Reinke
Kentucky Derby Horse Racing

A spectator wears a fancy hat through the paddock area before the 138th Kentucky Derby horse race at Churchill Downs Saturday, May 5, 2012, in Louisville, Ky. (AP Photo/Mark Humphrey)

Mark Humphrey
Kentucky Derby Horse Racing

Tamara Sorrell, from Austin, Tx., wears a fancy hat in the paddocks before the 138th Kentucky Derby horse race at Churchill Downs Saturday, May 5, 2012, in Louisville, Ky. (AP Photo/Mark Humphrey)

Mark Humphrey
Kentucky Derby Horse Racing

A spectator wears a fancy hat before the 138th Kentucky Derby horse race at Churchill Downs Saturday, May 5, 2012, in Louisville, Ky. (AP Photo/David J. Phillip)

David J. Phillip
Kentucky Derby Horse Racing

Tammy Behr, from Louisville, Ky., wears a fancy hat while attending the running of the 139th Kentucky Oaks at Churchill Downs Friday, May 3, 2013, in Louisville, Ky. (AP Photo/Charlie Riedel)

Charlie Riedel
APTOPIX Kentucky Derby Horse Racing

A fan wears a hat before the 142nd running of the Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2016, in Louisville, Ky. (AP Photo/Julio Cortez)

Julio Cortez
APTOPIX Kentucky Derby Horse Racing

Ashley Cebak and Tami Purcell wear hats before the 140th running of the Kentucky Derby horse race at Churchill Downs Saturday, May 3, 2014, in Louisville, Ky. (AP Photo/David Goldman)

David Goldman
Kentucky Derby Horse Racing

Nichole Whelan wears a hat before the 141st running of the Kentucky Derby horse race at Churchill Downs Saturday, May 2, 2015, in Louisville, Ky. (AP Photo/David J. Phillip)

David J. Phillip
Kentucky Derby Horse Racing

Ginny Keen wears a hat before the 141st running of the Kentucky Derby horse race at Churchill Downs Saturday, May 2, 2015, in Louisville, Ky. (AP Photo/Brynn Anderson)

Brynn Anderson
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