Kentucky Derby Hats

MISS: Jordin Sparks

If you're daring enough to wear purple streaks in your hair, then take a hat risk! Jordin's combo is just too dull for Derby day.

MISS: Vanessa Minnillo

We love an all-black outfit, but this headpiece is just too petite and reminiscent of Damon Wayans's hat catastrophes during In Living Color's "Men on Film" moments.

HIT: Marisa Miller

Taking a flapper-inspired approach works wonders to showcase this Thoroughbred's golden mane.

MISS: Maria Menounos

Oh, Maria. We love you but this silly sculpted hat is wearing you and taking attention away from that pretty face.

HIT: Erin Andrews

It's best to stick with neutral colors when going for such an elaborate headpiece, but Erin has the personality to pull off such an over-the-top hat.

MISS: Aubrey O'Day

Although something ornate is Derby Day appropriate, this hat is a tad matronly for such a filly.

HIT: Rozonda "Chilli" Thomas

Chilli keeps it cool, pairing a tasteful black hat with her strapless floral dress.

MISS: Julie Benz

Red with black tulle is a bit too bordello for a Derby Day VIP.

HIT: Betsey Johnson

Betsey keeps it fun with a quirky striped hat.

HIT: Bonnie-Jill Laflin

The equestrian dress and diamond horseshoe earrings are a little much, but taking a risk in Louisville is always a good thing. Giddyup!

HIT: Melissa Biggs

This Baywatch actress keeps the mystery behind her ever-so-classic white-rimmed hat.

HIT: Crowd Pleaser

While the celebs in attendance may have had 3-1 odds of winning the Triple Crown, we think these real women gave them a run for their money.

A statement hat makes you easy to spot in the crowd after one too many mint juleps. Your friends will thank you later.

MISS: Spider Woman

This concoction is more tarantula than hat and a little frightening for anyone with arachnophobia.

HIT: Think Pink

Feathers: Check. Ribbons: Check. Southern belle: Check.

MISS: White Wedding

Is Billy Idol at Churchill Downs? Because this hat is a little more white wedding than race spectator.

MISS: Cheese Head

This fan needs to be reminded that the racetrack is in Kentucky, not Wisconsin.

HIT: Flower Patch

A lady is never too young to step out in a fashionable floral hat.

HIT: Neon Lights

Stand out in the crowd by turning up the color volume on an already bright hat.

HIT: Southern Comfort

Take a timeout from the hot Southern sun under this modern lady-like hat.