KENTUCKY DERBY

Kentucky Derby Fashion Is All About Big, Loud, Over-the-Top Hats

The Kentucky Derby has a red carpet like none other in the world. While the annual horse-racing event originated as an opportunity for Southern attendees to show off the latest spring fashions, today more often than not women eschew contemporary trends for more traditional looks, complete with pretty dresses and statement-making hats, with eclectic twists. Hats have been a signature of the Kentucky Derby since the beginning, as a symbol of good luck, but over the years the hats have become more and more elaborate. Celebrities and spectators alike take their looks very seriously, preparing months ahead of time, wearing custom made hats and fabulous fascinators, depending on where they are seated: traditionally, guests in the seated sections of Churchill Downs prefer more elegant styles, like wide-brimmed hats, while those in the Infield traditionally wear hats that are a bit more eccentric and themed, like a fascinator. Colorful and floral, spring dresses are also a staple fashion at the Derby, having come from the desire to create a rainbow sea to anyone looking into the crowd. From southern bells to famous faces, here’s a look at how Kentucky Derby fashion has changed through the years.

1
1955
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These spectators came dressed to impress in printed, playful dresses that would become a signature of Kentucky Derby fashion for years to come.

2
1956

Here, a spectator heading to sit in ‘millionaire row’ wearing a fur coat over her printed dress with a playful bag and coordinating hat.

3
1977
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Looking very ’70s with their feathered hairstyles and form-fitting tops, these women eschewed tradition by going hat-less. Though hats represent good luck, they are not required for attendees.

4
1988
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In a nod to tradition, this Derby fan cheered on the race in a black and white polka dot jacket with a wide brim hat.

5
1993

Wearing a hat inspired by the Derby’s official flower–the rose–this fan was the center of attention in the ’90s.

6
1998
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This fabulous duo represents traditional Kentucky Derby fashion–with a very ’90s spin!

7
2010

Model Marissa Miller took a full step into spring and embraced tradition wearing very light pastel and a matching wide-brim hat.

8
2010
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Ashlee Simpson and Pete Wentz attended the 136th Kentucky Derby in retro ensembles.

9
2013
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Actress Krysten Ritter looked like a sweet, southern bell in Dolce & Gabbana at the 139th Kentucky Derby.

10
2013
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Shannon Voss referenced the Kentucky Derby’s garland of roses with a rose-covered cape at the 139th Kentucky Derby.

11
2014
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Nina Davuluri attended the 140th Kentucky Derby in a brightly colored dress complete with floral patterns.

12
2014
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The red rose is the official flower of the Kentucky Derby, and a symbol that attendees love to incorporate into fashion. This guest proved that point in 2014.

13
2014
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News anchor Robin Meade attended the 140th Kentucky Derby dressed in spring pastels and a slightly smaller-than-traditional hat.

14
2014
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Figure skater Johnny Weir loves to draw a crowd with his outrageous hats at the derby. Here at the 140th Kentucky Derby, he was dressed all in white to match his feathered fascinator.

15
2015
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Courtney Sixx’s look popped at the pre-Derby Ladies luncheon. Her sunshine yellow sundress may stand out, but the true star of this look is her over the top hat complete with a wide brim and decorated with ribbon and florals.

16
2016
Frazer Harrison

Singer K. Michelle attended the 142nd Kentucky Derby in a black skirt and voluminous crop top with a coordinating, over-the-top statement hat.

17
2016
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Rachel McCord was pretty in pink at the 142nd Kentucky Derby in a floral printed dress, and an elegant hat.