I must admit, I asked the question about Sarah Vickers' recent outfit... under anonymous for fear of backlash after insulting the taste of Tumblr's queen of prep. However, I must express my gratitude for your excellent response! Your advice is wonderful, and so enjoyable to read. You seem to dedicate so much time and thought to each of your answers. Thank you!
I'm a guy, and I need some ideas for labels that are definitely preppy but at the same time fashion-forward. What fits my taste ever since is J Crew, and almost all my clothes have been J Crew; I'm kind of getting sick of it and want a wider variety. I don't know if this will be unorthodox (perhaps even blasphemous), but I want to experiment into the "prepster" (preppy + hipster) look. So any ideas?

