Or rather, what would Holden Caulfield wear if he were a real person alive in 2010, with a budget that stretched to designer clothes?

This blog is one person's imaginings of what famous ficitonal and historical characters would wear these days:

http://textbook.tumblr.com/characterindex

I'm most familiar with the Jane Austen characters, and think this guy gets them mostly right. But Lydia Bennet would definitely wear shorter dresses than the ones he chose. It's lots of fun thinking about it!