Our Favorite Celebrity Derby Hats of All-Time

We think Cyndi Lauper wins for biggest hat.

May 4, 2018
Cyndi Lauper

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You know when you're headed to Churchill Downs that you're about to see some of the best (?) fashion has to offer in the hat department. As they do, some of our celebrities took the originality of Derby hats and made them that much more exotic. Here are our favorite celebrity Derby hats of all-time -- and yes, it's about to get weird.

Tara Lipinski & Johnny Weir
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Tara Lipinski and Johnny Weir

We were OBSESSED with their coordinating outfits at the Sochi Olympics but it turns out they've been rocking their style together for awhile!! As always, they shut down the red carpet with these looks!

 

 

 

 

 

 

 

 

 

 

 

 

Miranda Lambert
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Miranda Lambert

Miranda Lambert
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Miranda Lambert
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Over the years, Miranda has rocked a few eye-catching hats at the Kentucky Derby... if I was forced to choose a favorite? There's just something about her in red!

 

 

 

 

 

Mary J Blige
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Mary J Blige
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Mary J. Blige

As always, she looked AMAZING when she attended the Kentucky Derby to sing the National Anthem.

( We are VERY much about those gloves & that amazing dress too!! Oh, and her voice of course - that goes without saying!)

 

 

 

Cyndi Lauper

Cyndi Lauper
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Cyndi Lauper
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She wins for the biggest hat, I mean look at that brim! It has to be over a foot... I'd be accidentally smacking people in the face with that for sure.

  

 

Jordin Sparks
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Jordin Sparks

She looks gorgeous! There truly isn't anything about this to not-like. 

 

 

 

 

 

 

 

 

Brooke Shields

Brooke Shields
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We're loving the navy blue!! 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Gabrielle Union

Gabrielle Union
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Black & gold is classic and she looks BEAUTIFUL.