It's me, Jena, the rarely seen in the wild Wearability contributor!
Anyway I have a site recommendation, and here's hoping no one has heard of it yet:If you're a window shopper, app devotee, or closet paper doll hobbyist, you might like building an ensemble on Polyvore. I spent a good thirty minutes there trying to come up with an outfit for a theoretical date to a theoretical 40's style cocktail party. A lot of the selections are expensive, but I spotted a couple mid-range items in there (Forever 21?) Anyway it's pretty intuitive and I'm curious to see what people put together.