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Home • Street Style

Street Style: All The Showstopping Kentucky Derby Hats & Dresses

See all the fabulous frocks and extreme toppers attendees wore to the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.
By Joslyn Blair · Updated October 27, 2020
01
Derby Divas

Nari Williams attends the 142nd Kentucky Derby at Churchhill Downs in a Sophia Collection dress.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
02
Derby Divas

Nari Williams attends the 142nd Kentucky Derby at Churchhill Downs in a Berkley Hat Co. hat.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
03
Derby Divas

Miss Kentucky Clark Davis attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
04
Derby Divas

Miss Kentucky Clark Davis attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
05
Dapper at the Derby

Kenya and Dustin Leger attend the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
06
Derby Divas

Amelia Geathers attends the 142nd Kentucky Derby at Churchhill Downs in a Rose Street Boutique hat, Rachel Roy dress and Vince Camuto shoes.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
07
Derby Divas

Krystal Sobers attends the 142nd Kentucky Derby at Churchhill Downs in an Amazon Facinator, GoJane Dress and Aldo shoes.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
08
Derby Divas

Krystal Sobers attends the 142nd Kentucky Derby at Churchhill Downs in an Amazon Facinator.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
09
Derby Divas

Kim Franklin attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
10
Derby Divas

Kim Franklin attends the 142nd Kentucky Derby at Churchhill Downs in an Alanta Boutique hat.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
11
Dapper at the Derby

Ian Cevr attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
12
Derby Divas

Inez Henry attends the 142nd Kentucky Derby at Churchhill Downs in a Lady J hat and Dress Barn dress.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
13
Derby Divas

Inez Henry attends the 142nd Kentucky Derby at Churchhill Downs in a Lady J hat.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
14
Dapper at the Derby

Cheryl and Bill Fisher attend the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
15
Dapper at the Derby
Dwayne Franklin attends the 142nd Kentucky Derby at Churchhill Downs in Goorin Brothers hat.
Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
16
Derby Divas

Crystal Witherspoon attends the 142nd Kentucky Derby at Churchhill Downs in Gabriel Amar hat, Trina Turk dress and Aquazzura Shoes.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
17
Derby Divas

Crystal Witherspoon attends the 142nd Kentucky Derby at Churchhill Downs in a Gabriel Amar hat.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
18
Derby Divas

Amber Caillier attends the 142nd Kentucky Derby at Churchhill Downs in a Dillards hat and dress.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
19
Derby Divas

Chastity Westry attends the 142nd Kentucky Derby at Churchhill Downs in a hat from Etsy, and Channel and David Yur jewelry.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
20
Derby Divas

Chastity Westry attends the 142nd Kentucky Derby at Churchhill Downs in a hat from Etsy.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
21
Derby Divas

K. Michelle arrives at the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Nicholas Hunt/Getty Images
22
Derby Divas
K Michelle attends the 142nd Kentucky Derby at Churchhill Downs.
Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Nicholas Hunt/Getty Images
23
Dapper at the Derby

LaTanya and Michael White attend the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
24
Derby Divas

LaTanya White attends the 142nd Kentucky Derby at Churchhill Downs in an Antonio Aloni hat.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
25
Derby Divas

Gayle King attends the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Nicholas Hunt/Getty Images
26
Derby Divas
Gayle King arrives at the 142nd Kentucky Derby at Churchill Downsin Louisville, Kentucky.
Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Nicholas Hunt/Getty Images
27
Dapper at the Derby

Ray J and Princess Love arrive at the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Nicholas Hunt/Getty Images
28
Derby Divas

Star Jones attends the 142nd Kentucky Derby at Churchill Downs on May 07, 2016 in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Frazer Harrison/Getty Images
29
Derby Divas
A guest attends the 142nd Kentucky Derby at Churchill Downs on May 07, 2016 in Louisville, Kentucky.
Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Michael Noble Jr./Getty Images
30
Dapper at the Derby

Sharonda Jones and Shawn Stockman attends The 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Stephen J. Cohen/WireImage
31
Derby Divas

A guest attends The 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Stephen J. Cohen/WireImage
32
Derby Divas

A guest attends The 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Stephen J. Cohen
33
Derby Divas

Jennifer LeGrande attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
34
Derby Divas

A guest attends the 142nd Kentucky Derby at Churchill Downs in Louisville, Kentucky.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Frazer Harrison/Getty Images
35
Derby Divas

Daemon Jones attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
36
Dapper at the Derby

A stylish couple attends the 142nd Kentucky Derby at Churchhill Downs.

Street Style: All The Showstopping Kentucky Derby Hats & Dresses
Winkfield Photography
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