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Slideshow: Kentucky Derby Hat Fashion - Who Wore It Best?

May 4th, 2009 2:20pm EDT Post a comment

Brooke Shields

Check out the hats celebrities wore to the Kentucky Derby on Saturday. Who wore the best (or worst!) hat? Click through our photo slideshow, and let us know!

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16 Member Comments

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Mon May 4 2009 14:35:04 By: OrlandoLuver (

1492)
The good: Marg Helgenberger
The Bad: Joey Fatone
The Ugly: Booke Shields

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Mon May 4 2009 14:36:43 By: chunky lover 53 (

14467)
One thing is for sure from this sideshow, They'll let anyone into the Derby.

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Mon May 4 2009 14:40:27 By: Tom Sizemore (

18677)
I missed it, did Sarah Jessica Parker edge out Hilary Swank for the win?

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Mon May 4 2009 14:48:18 By: RUSHmusicfan (

429)
Why do we care?

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Mon May 4 2009 14:53:43 By: Marcus Garvey (

4196)
marg helgenberger and kim kardashian look the best. the chick from real housewives looks like mena suvari on crack

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Mon May 4 2009 15:20:52 By: cat27 (

1967)
Marg H and Valerie B look great as does Ms. Kardashian who demonstrates while money can't buy class (or talent) it CAN buy really nice clothes!

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Mon May 4 2009 16:14:17 By: nicerack (

8973)
I hate hats, i think Kid Rock wore the best hat or cap, whatever.

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Mon May 4 2009 16:24:30 By: Tom Sizemore (

18677)
It looks like Brooke I-aged-25-in-5-years Shields' head is being abducted by aliens.

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Mon May 4 2009 17:34:49 By: I_B_FRIENDLY (

7288)
What is up with those big F_cking Hats?

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Mon May 4 2009 20:22:08 By: SOME_GIRL (

3361)
^People...they are derby hats...it's tradition...there is even a milliner on the grounds. Brooke's dress is too short and her shoes are horrid...Kim looks outstanding.

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Mon May 4 2009 20:23:03 By: SOME_GIRL (

3361)
@ Marcus...Mena Suvari looks like Mena Suvari on crack, have you seen her lately?

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Tue May 5 2009 00:06:12 By: edifier (

4)
Shields usually looks good but here - yuk. Dress too short, random ugly hat. Kim looks lovely.

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Tue May 5 2009 16:05:33 By: Rondel10 (

122)
I couldn't get past Bethenny's photo .... God-awful.

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Tue May 5 2009 17:14:11 By: user193 (

531)
i've seen better lids on a toilet.