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Edited by on May 6 2011 at 12:13 PM

The Kentucky Derby is tomorrow, meaning extravagant hats, mint juleps and drunk gambling are on the horizon. There are few things that could ruin such a glorious day in our beautiful American South, and some celebrities came really close to doing so. In this edition of Red Carpet Report Card, we will look at the best and worst dressed of the 2010 Kentucky Derby. Hopefully everyone can learn a little something about how to look like a lady for the big event tomorrow.

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

Let’s start with the best of the Derby, the Southern Belles who embodied the spirit of the event in a tasteful and classic manner.

Johnny Weir is the winner of best dressed! He looks amazing in his dandy ensemble and gorgeous oversize hat.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

Ashley Simpson looks absolutely adorable (something I don’t get to say very often) in her cloche hat, pearls and polka dots. It’s 1922 at the Derby and she is in high style. But I wish she would have put her hair up.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

I love this bright periwinkle dress Jaime Pressly chose to pair with her dark hat and shoes. But I can’t tell if the dress is wrinkled or not, which is a little irritating to the eye.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

Doesn’t LeAnn Rimes embody the spirit of the Derby perfectly? I really adore the floral mini dress and how the ribbon on her elegant straw hat matches it to a T. I would have done a different shoe, but that’s me.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

Joey Fatone is certainly N*SYNC with the festivities (forgive me, it’s Friday and I’ve already started with the juleps). Give me red roses and feathers any day of the week.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

This is a very special photo that will take us from the best dressed at the Derby to the worst dressed. Kim Kardashian looks absolutely gorgeous. Her look is sexy and sophisticated, and I especially love the hat and wrist gloves. Brava, Kim.

Kris Kardashian on this other hand looks a mess. This dress is not flattering on her and the patent leather stripper shoes were a poor choice for the event. AND I could make a leather tote bag out of her sun damaged skin. Bad, bad, bad.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

God in heaven, save us from the evil that is Brooke Shields‘ hat. It seriously looks like her whiny kids made it for her in school – a failed attempt on Brooke’s choice to wear it and the children for being poor crafters. And I think I had this same dress when I was five, so maybe she borrowed it from her daughters too?

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

I was a little torn here, because all of these hats are fabulous. Kenda look bangin’, she is actually one of the best dressed in my opinion. HOWEVER, where in Satan’s hell did Bridget and Holly get those dresses? Macy’s junior department prom section is about on par with these disasters, couldn’t they get anything better? Wait, probably not. Hef also looks pretty fly for a 200-year-old man.

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

An all black outfit to the Derby? Are you f*cking kidding me Gabrielle Union? In the words of Carrie Bradshaw‘s unfortunate party girl friend Lexi Featherston, “I’m so bored, I could die.”

 

 

RED CARPET REPORT CARD: Best & Worst of Kentucky Derby 2010

And here it is, the absolute worst outfit of the 2010 Kentucky Derby. Bethenny Frankel opted for a light pink seersucker jumpsuit with matching ruffle, side tail and hat. But I think the lollipop is what pisses me off the most. It kind of looks like she wrapped herself in a baby blanket, no?

 

I hope you enjoyed this very special Kentucky Derby edition of Red Carpet Report Card. Stay tuned for the best and worst dressed at this year’s event next week.

 

 

 

Story by Amanda Gabriele

I stole my first pair of platforms from the Spice Bus in 1997 when Anglophilia was all the rage. Collector of vintage bags, vinyl and kitchen appliances. My dream of becoming a butcher is momentarily on hiatus so I can teach you how to wear muumuus and apply false eyelashes. Follow me on Twitter @CrystlMeatballs.