Edited by Amanda Gabriele on
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.
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.
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.
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.
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.
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.
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.
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?
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.
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.”
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.