Over-the-Top Hats from Kentucky Derby
- Next1 of 25Theo Wargo/WireImage
- Previous Next2 of 25Joey Foley/Getty Images for Moet
- Previous Next3 of 25Jeff Gentner/Getty Images for New Era
- Previous Next4 of 25Michael Loccisano/Getty Images
- Previous Next5 of 25Jeff Gentner/Getty Images for New Era
- Previous Next6 of 25Joey Foley/Getty Images for Moet
- Previous Next7 of 25Michael Loccisano/Getty Images
- Previous Next8 of 25Joey Foley/Getty Images for Moet
- Previous Next9 of 25Stephen J. Cohen/WireImage
- Previous Next10 of 25Michael Loccisano/Getty Images
- Previous Next11 of 25Michael Loccisano/Getty Images
- Previous Next12 of 25Stephen J. Cohen/WireImage
- Previous Next13 of 25Michael Loccisano/Getty Images
- Previous Next14 of 25Matthew Stockman/Getty Images
- Previous Next15 of 25Matthew Stockman/Getty Images
- Previous Next16 of 25Jamie Squire/Getty Images
- Previous Next17 of 25Elsa/Getty Images
- Previous Next18 of 25Matthew Stockman/Getty Images
- Previous Next19 of 25Matthew Stockman/Getty Images
- Previous Next20 of 25Elsa/Getty Images
- Previous Next21 of 25Matthew Stockman/Getty Images
- Previous Next22 of 25Jamie Squire/Getty Images
- Previous Next23 of 25Elsa/Getty Images
- Previous Next24 of 25Elsa/Getty Images
- Previous Next25 of 25Matthew Stockman/Getty Images
And They're Off!1 of 25
The greatest two minutes in sports always brings out the greatest two minutes in hats. See which Kentucky Derby toppers (on real women and celebs) made the winner's circle, and which were left in the dust. —Alexis Jonnson
HIT: Although most ladies opt for sugary sweet pastels at the Kentucky Derby, Debra Messing keeps it classic in a dove gray sun hat with subtly patriotic red, white and blue accents.
Whoa Boa2 of 25
MISS: While we love the violet floral dress, the boa belongs more in the bedroom than at the Derby.
Earning Her Stripes3 of 25
HIT: Typically, Coco Austin's outfits make us shield our eyes, but Ice-T's other half tones it down (for her) in nautical stripes and a matching red and white hat.
Coming Up Roses4 of 25
HIT: With her fedora-like topper, Mary J. Blige belted out the national anthem at this year's race while staying true to her style.
Re-Think Pink5 of 25
MISS: Step away from the glue gun. Orange County Real Housewife Vicki Gunvaison's hodgepodge of a hat looks like a craft project gone awry.
Go Wide6 of 25
HIT: A strip of lace netting breaks up the brim on this dramatic hat on Style Network host Jeannie Mai and keeps it from being too overpowering.
Red Square7 of 25
MISS: Ginnifer Goodwin's look is too buttoned up for the Derby and needs to let her playful side out of the gates.
Orange You Glad?8 of 25
HIT: Erin Andrews is picture perfect in a hat accented with one of this season's hottest hues.
For the Birds9 of 25
MISS: It looks as if a flock of birds crash-landed on Star Jones' lopsided topper.
Shine On10 of 25
HIT: Tennis star Stefi Graff shines in metallics and neutrals.
Just a Little Bit11 of 25
MISS: Miranda Lambert's small topper is more appropriate for a funeral and not a day of racing fun.
Gentleman Caller12 of 25
HIT: Ashton Kutcher keeps it dapper in a neutral newsboy cap and retro shades, although we wouldn't mind if he shaved.
Flower Girl13 of 25
HIT: The 5-year-old daughter of Anna Nicole Smith, Dannielynn Birkhead, looks adorable in a matching yellow rose dress and hat.
Blue Belle14 of 25
HIT: "I'll Have Another" may have won the Derby, but this bright topper leads the style pack with a pop of beautiful blue against crisp white.
Lost Cause15 of 25
MISS: Come out, come out wherever you are... This hat defines over-the-top, but where's the woman who's wearing it?
Faking It16 of 25
MISS: The faux geraniums are a real disappointment.
Futurama17 of 25
HIT: This is one loud piece, but the wearer owns the hat by pairing it with retro shades.
Lime Life18 of 25
MISS: We love a neon accessory but this lime green concoction and matching crystal earrings are overkill.
Black Magic19 of 25
HIT: This silk top hat is a bit drab for the Derby, but wins points for its Mad Hatter shape.
Under Cover20 of 25
HIT: Perfect for those who like to stay out of the sun (or the spotlight), this bonnet hides its wearer in hot pink.
Dull & Oats21 of 25
MISS: This oatmeal-hued style does nothing for a woman's style (or her complexion) and looks too much like an unfinished needlepoint project.
Purple Reign22 of 25
HIT: This year's first place jockey wore purple proving that the regal hue is a sure winner.
Brown Out23 of 25
MISS: While we love the angles and accents of this hat, we'd like to have seen it in a more eye-catching color.
Small Wonder24 of 25
HIT: A well-designed bouquet is a delightful way to accent a tiny topper.
Simple Plan25 of 25
HIT: Even if hats aren't your thing, this classic black and white number won't scare you away.