Gossip Girl hunk Penn Badgley had a serious brooding expression as he posed at the Target Kaleidoscope Fashion Spectacular on Wednesday, but we can’t help smiling at his rolled-up pants that reveal that even his ankles are sexy!

30 Rock star Katrina Bowden showed off her perky smile and playful persona in a belted summer dress and strappy sandals.

The City star Roxy Olin enjoyed a night out in the city at the Target party.

Socialite Olivia Palermo took a fashion risk – and won! – in a striped blazer and leather shorts. We loved the ruffled shirt peeking out underneath.

Despite the colorful theme, Weeds star Mary-Louise Parker kept it dark and serious in black crochet and tights – an unusual choice for a hot summer night.

Project Runway judge Nina Garcia would have given herself a glowing review for her detailed frock-top and skinny jeans.

Luigi Tadini channeled geek chic in dark rimmed glasses and mis-matched shirt, jacket and tie combo.

Sammy Swetra captured a youthful elegance in a patterned frock and sheer panel.