Photo: Hot Beauty Health

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.

It’s Friday, which means it’s time for another history of costume lesson. Looking back to the speakeasy era of U.S. prohibition, depriving people of alcohol inspired really cool fashions and devious behavior. One of my favorite accessories of the flapper age is the oh-so-stylish cloche hat. But this iconic piece was popular well before the 1920s; the helmet-shaped hat was developed in 1908 and considered one of the most extreme forms of millinery. When worn properly, the cloche covered the eyes and often added inches of height. It would cause the wearer to lift the head and peer down the nose in order to see, usually resulting in a pretentious air.

Art Deco influence could be seen in some of the seams and line construction, especially when stitched in a zigzag design. The bulbous shape and elaborate appliqués were considered radical for the time, but the cloche became more acceptable as woman started wearing makeup. Once the initial shock of this style wore off, it became readily acceptable and a symbol of feminine style and refinement.