Crazy Hats of the Kentucky Derby

The hats of the Kentucky Derby nearly cast a shadow over the horse race itself. Here are a few of the craziest hats seen at the race in recent years.

36 photos
1/36
Getty Images
TV personality Monte Durham, ESPN sports analyst Holly Huggins, Fox News reporter Bonnie-Jill Laflin and Mary Wilson of The Supremes at the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
2/36
Getty Images for Churchill Downs
Model Kate Upton at the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
3/36
Getty Images for Churchill Downs
Singer Hillary Scott of Lady Antebellum attends the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
4/36
Getty Images for Churchill Downs
Football players Terrell McClain and Melton Henry attend the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
5/36
Getty Images for Churchill Downs
Singer Jordan Smith and his girlfriend Kristen Denny attend the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
6/36
Getty Images for Churchill Downs
Singer J. D. Shelburne and fiance Amy Whitham attend the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
7/36
Getty Images
Singer Ray J and Princess Love arrive at the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
8/36
Getty Images for Churchill Downs
Football player Bilal Powell and Jessica Powell attend the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
9/36
Getty Images
Miss Kentucky's Outstanding Teen 2015 Kennedy Sabharwal arrives at the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
10/36
Getty Images for Churchill Downs
A derby hat at the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
11/36
Getty Images
Racegoers take a selfie in the infield prior to the 142nd running of the Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
12/36
Getty Images
Hats, high fashion, and revelry dominate the scene on Kentucky Derby Day as fans walk through the tunnels to the infield at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
13/36
Getty Images for Churchill Downs
A woman wears a Derby hat at the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
14/36
Getty Images for Churchill Downs
Courtney Sixx is seen around the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
15/36
Getty Images
Racegoers take selfies in the infield prior to the 142nd running of the Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
16/36
Getty Images for Churchill Downs
American World Cup alpine ski racer Lindsey Vonn attend the 142nd Kentucky Derby at Churchill Downs on May 7, 2016, in Louisville, Kentucky.
17/36
AP
A fan wears a hat before the 142nd running of the Kentucky Derby horse race at Churchill Downs, May 7, 2016, in Louisville, Kentucky.
18/36
WireImage
A general view of atmosphere during the 141st Kentucky Derby at Churchill Downs on May 2, 2015, in Louisville, Kentucky.
19/36
AP
Sara Ward looks up before the 141st running of the Kentucky Oaks horse race at Churchill Downs Friday, May 1, 2015, in Louisville, Ky.
20/36
Getty Images
A woman wearing festive hats looks on in the paddock area prior to the 141st running of the Kentucky Derby at Churchill Downs on May 2, 2015, in Louisville, Kentucky.
21/36
WireImage
A general view of atmosphere during the 141st Kentucky Derby at Churchill Downs on May 2, 2015, in Louisville, Kentucky.
22/36
Getty Images
A woman wearing a festive hat looks on prior to the 141st running of the Kentucky Derby at Churchill Downs on May 2, 2015, in Louisville, Kentucky.
23/36
WireImage
LOUISVILLE, KY - MAY 02: A general view of atmosphere during the 141st Kentucky Derby at Churchill Downs on May 2, 2015 in Louisville, Kentucky. (Photo by Stephen J. Cohen/WireImage)
24/36
WireImage
A general view of atmosphere during the 141st Kentucky Derby at Churchill Downs on May 2, 2015, in Louisville, Kentucky.
25/36
WireImage
LOUISVILLE, KY - MAY 02: Tara Lipinski and Johnny Weir attend the 141st Kentucky Derby at Churchill Downs on May 2, 2015 in Louisville, Kentucky. (Photo by Stephen J. Cohen/WireImage)
26/36
AP
Cassie Foomar wears a hat before the 141st running of the Kentucky Derby horse race at Churchill Downs Saturday, May 2, 2015, in Louisville, Ky.
27/36
AP
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.
28/36
AP
A woman looks over the paddock area before the 141st running of the Kentucky Derby horse race at Churchill Downs Saturday, May 2, 2015, in Louisville, Ky.
29/36
AP
Terry Vanzant of Denver, Colo., wears a hat before the 136th Kentucky Derby horse race at Churchill Downs Saturday, May 1, 2010, in Louisville, Ky.
30/36
AP
Desirae Masterson, from Indianapolis, Ind., with her hat covered in a plastic bag to protect it from the rain, shares a mint julep with her husband Ray before the running of the 139th Kentucky Derby at Churchill Downs Saturday, May 4, 2013, in Louisville, Ky.
31/36
ASSOCIATED PRESS
Eric Williams of Chicago wears a hat honoring last year's winner of the Kentucky Derby Barbaro at Churchill Downs in Louisville, Ky., Saturday, May 5, 2007.
32/36
AP
Christen Edelen, from Louisville, Ky., uses a plastic bag to protect her hat from the rain before the 136th Kentucky Derby horse race at Churchill Downs Saturday, May 1, 2010, in Louisville, Ky.
33/36
AP
Jim LaRochelle, of Evanston, Ill, wears a smiling box hat is kissed by Susan Helms, of Chicago, during Kentucky Derby day festivities at Churchill Downs, Saturday, May 1, 2004, in Louisville, Ky.
34/36
AP
Skip Koepnick, from Wyoming, Mich., shows off his Derby hat before the 137th Kentucky Derby horse race at Churchill Downs Saturday, May 7, 2011, in Louisville, Ky.
35/36
ASSOCIATED PRESS
Charles Matasich of Proctorville, Ohio, wears a colorful hat of roses as he looks over the paddock during Kentucky Derby festivities at Churchill Downs, Saturday, May 1, 2004, in Louisville, Ky.
36/36
AP
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.
Contact Us