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

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.

Best

Mary J. Blige

Mary J. Blige is very much a “Lady in Red.” 

Debra Messing

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

Read Charlize Theron + More Celebs Who Were Fab or Drab at the Correspondents Dinner

Erin Andrews

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

Jeannie Mai

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

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, Miranda Lambert and other worst-hatted at the Kentucky Derby up next!