There is quite the range of fashion on that show, it definitely contributes to the awkwardness. One of my favorite bloggers, Joanna Goddard from A Cup of Jo had the privilege of interviewing Girls costume designer, Jenn Rogien.
I found the interview absolutely fascinating. Go read it here.
A close second would be Marnie. She tends to dress more business than I would. Think fitted dresses, pearls, and pumps.
A part of me wish I were bold enough to dress like Jessa. Not the MC hammer pants and insane prints, but the 80's style hats and 60's style dresses. She's very eclectic though.
Then there's Hannah. Some of her clothes are cute, really cute. She just wears them all wrong.
You can watch Girls Sunday nights, on HBO.