54 Photos Of Badly Dressed Celebrities, Large Hats, And Drunk People At The Kentucky Derby

Horses aside, this race is about three things: famous people, headgear, and getting trashed. Here, a complete photo recap of the Derby.

First, the celebrities.

1. Debra Messing.

Michael Loccisano / Getty Images

Oh this is even worse than her terrible “Smash” outfits.

2. How’d she get tricked into this?

Theo Wargo / Getty Images

Is this the celebrity’s version of “what was I thinking when I was drinking last night?” Instead of like, “what ex-boyfriend did I text,” what crazy-looking red people did I pose for photos with?

3. Gail Simmons

Michael Loccisano / Getty Images

I think she was there to plug tea that comes in a salad dressing bottle — an occasion that makes this outfit absolutely outstanding. (I’d have shown up in a tracksuit were this my duty.)

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5. Star Jones

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If My Little Pony were a dress and hat this is what it would look like.

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7. Mary J. Blige

Joey Foley / Getty Images

She looks far too reasonable to be here. Also, she is cool, so why is she here?

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9. Christian Siriano

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Remember this Project Runway winner? He evidently salvaged part of the Pan Am wardrobe for this occasion.

10. Kate Flannery

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It’s the Kentucky Derby, not the Zoro Derby — wrong hat, Kate.

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12. Ice T and Coco

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They are perfect always. (Her adorable day dress is Juicy Couture, by the way.)

13. Coco

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14. Sharni Vinson and Kellan Lutz

Theo Wargo / Getty Images

She is one of the best-dressed of this whole thing. He looks like he raided Tom Brady’s closet. But he’s so attractive he can pretty much get away with anything.

15. Miranda Lambert

Theo Wargo / Getty Images

I appreciate her sequined fascinator!

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17. Erin Andrews

Joey Foley / Getty Images

She looks like she’s going to a wedding, but I guess that’s kind of The Look at this thing.

18. Bonnie-Jill Laflin

Joey Foley / Getty Images

A rogue purple boa masquerades as hair fungus.

19. Cyndi Lauper

Joey Foley / Getty Images

I can’t say anything bad about Cyndi Lauper. Her tomato dress was a clever choice.

20. Ginnifer Goodwin

Michael Loccisano / Getty Images

This is the kind of dress that would look fashionable at a fashion event but just looks really dorky at something like this.

21. A model wearing an outfit made of roses.

Michael Loccisano / Getty Images

Apparently stringing some roses together and wearing a few strands at once qualifies as a top. How have slutty Halloween people not figured this out yet?

22. Dannielynn Birkhead

Michael Loccisano / Getty Images

She looked disturbingly gorgeous/perfect for her young age.

23. First prospective boyfriend for Dannielynn Birkhead.

Stephen Cohen / Getty Images

Hipster toddler.

24. Second prospective boyfriend for Dannielynn Birkhead.

Jamie Squire / Getty Images

Preppy toddler (with a boutonniere).

And now, the fabulously large hats.

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People who are getting drunk…

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And the drunk people.

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