Between picking out first-edition Oscar Wilde novels and marveling at the sleeping nooks of Shakespeare and Co in Paris, we spotted this subversively preppy dude. At first glance his look seems rather tame, but his super-high rolled-up pants made us trip. He's rocking collegiate staples— wool peacoat, white oxford shirt and argyle socks—but breaks up the norm with the lower half of his look. After we snapped this pic, he went upstairs and softly played the in-house piano while his girlfriend read to him, a little afternoon folly for one scholarly gent.