Debra Messing

This could only be suitable at the races, or at some 1950s summer picnic. Debra aims for elegance here, but the shapeless, unflattering cut means she just looks like a column of grey. She could even pass for a vase what with that flower- adorned hat.

Photo by Getty Images May 8, 2012

WHAT WERE THEY THINKING?!

From dismal derby day outfits to jaw-dropping plunging necklines, this week's worst-dressed celebs include Adrienne Bailon, Rihanna, and January Jones