What not to wear would be fun.
Though I really do think I would have a hard time shopping in New York. I'm used to the Midwest, where I'd probably never pay more than $30 for a shirt. When they show these outfits at the end, it's always "Here's Suzy in her $150 shirt, $400 pants, and $200 shoes."

That's two month's mortgage for me... I don't think I could wrap my mind around that!