Mary J. Blige, Kellan Lutz + More Celebrities and Their Wild Kentucky Derby Hats

At the annual Kentucky Derby, some celebrities' hats like Star Jones or Jeannie Mai outshone them!

-PJ Gach,

mary j blige kellan lutz jeanni maimary j blige kellan lutz jeanni mai

The Kentucky Derby, held at the famed race course the Churchill Downs, is known as the first step for racehorses to achieve the Triple Crown. It's also famed for mint juleps, Derby parties and hats. Oh the hats! When you place celebrities like Debra Messing, Cyndi Lauper and Erin Andrews in hats, sometimes it works and sometimes, well, it just looks like a bad joke.

Here are our 10 best and worst celebrity hats and the people who wore them.


Mary J. Blige

mary j, blige at the kentucky derbymary j, blige at the kentucky derby

Mary J. Blige is very much a "Lady in Red."

Debra Messing

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Smash star Debra Messing is a silvery delight at the Kentucky Derby.

Erin Andrews

erin andrews at the kentucky derbyerin andrews at the kentucky derby

ESPN sportscaster Erin Andrews is a tangerine dream in her large straw floppy hat and printed dress.

Jeannie Mai

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How do I look and Fashion Star's Jeannie Mai looks like she could be equally at home at a garden party, summer wedding or at the polo grounds.

Cyndi Lauper

cyndi lauper at the kentucky derbycyndi lauper at the kentucky derby

I'm not sure if this is really Cyndi Lauper. I mean, her hat is restrained and not Ka-razzy - you know, like the stuff she usually wears.


Kellan Lutz

kellan lutz at the kentucky derbykellan lutz at the kentucky derby

The whole outfit screams dancing extra from a '60s Disney musical, not Kellan Lutz, Twilight hottie.

Priscilla and Patricia Barnstable

priscilla and patricia barnstable at the derby 2012priscilla and patricia barnstable at the derby 2012

To the Barnstable sisters, Patricia and Priscilla, a word of advice: Twice is not always as nice.

Miranda Lambert

miranda lambert at the kentucky derby 2012miranda lambert at the kentucky derby 2012

While Miranda Lambert's fascinator says "posh event," the rest of the outfit... doesn't.

Kate Flannery

kate flannery at the kentucky derby 2012kate flannery at the kentucky derby 2012

OMG! The Office's Kate Flannery's hat matches her hair.

Star Jones

star jones at the kentucky derby 2012star jones at the kentucky derby 2012

Star Jones hat is so large, it could take flight.

Tell us: which hat did you love and which one did you hate?


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