
Saturday, May 7th marked the 137th annual “Run for the Roses” at iconic Churchill Downs in picturesque Louisville, Kentucky. Naturally, we look forward to the races every year, because our favorite stars come out in droves, sporting their fanciest toppers! Not unlike the recent Royal Wedding, no respectable A-lister would be caught dead at the Kentucky Derby without a fierce and fashionable hat. Unlike those over-the-top nuptials across the Pond, you won’t get turned away at the door if you opt to go hatless. Nonetheless, our favorite celebrities often play to Derby tradition and go all-out with their headwear.
The problem with Derby-worthy hats is that they can often look stuffy or matronly. It takes a true fashionista to make a wide-brimmed hat or birdcage-style fascinator look sexy. But leave it up to former Miss Teen USA, actress and model Vanessa Minnillo to do exactly that. Her haute hat, paired with a demurely sexy little black dress was both totally appropriate and downright drool-worthy. We never considered ourselves “hat people,” but may need to reconsider after seeing this stylish look! Read below for our best tips on how to work a headpiece like Vanessa.

For starters, the monochromatic black hue of Ms. Minnillo’s ensemble keeps the whole look streamlined and sexy. Too much color in a similar outfit might be overkill, and adding a hat would send the look straight to crazy town. The hemline of Vanessa’s LBD is super short, but perfectly balanced by a modest crewneck, cap sleeves and a feminine belt at her waist. And with a knockout body like hers, her tanned and toned gams are her second best accessory – besides her fabulous hat, of course!

Vanessa kept her Derby hat tiny and tasteful, but still fun. Smaller than a traditional wide-brimmed topper, but bigger than a headband-style fascinator, we love the proportion of her headpiece to the rest of her outfit. We also think she completed her look to perfection with a simple pair of pointy black pumps. Heartthrob fiancé Nick Lachey wasn’t a bad choice, either!
