I've always had a thing for boy's clothes. Back in high school, I thought I was making some sort of statement by wearing boys' oxford shirts and little blazers from the kids' section of Goodwill (I was obsessed with wearing the shirt from a Boy Scout uniform at one point). I still love menswear details: tweeds, pinstripes, and a crisp button-down. Even though I pretty much stick to lady clothes now, I was excited to see a new menswear line called Gilbert & Lewis (I love an ampersand in a title). They've got a great preppy-with-a-twist line, including gingham and madras (prints you can only get away with if you live in the American South). The line was designed for their Japanese clientele, so sizes run a little slimmer.
And maybe it's all the time I've spent in this town, but one of those red or blue gingham bow ties would charm the...er...socks off of me.