What is cool? Hard to say. Trying to define "cool" is a bit like trying to explain the taste of salt. It just is what it is. Something is either cool, or it's not. Peter Som has not, historically, proved a designer much interested in the particular codes and poses of cool; he likes a ladylike look, a tailored fit, a peppy print, a general atmosphere of poshness. So it was interesting, today, to see Som make a typically disciplined effort to conjure a slouchy downtown attitude.

The results were mixed. Som has a huge hit on his hands with his baggy watercolor print board shorts, part of a new denim collaboration with Earnest Sewn, and his graphic patchwork snakeskin was definitely punchy. Gold leopard trousers and a marled orange knit made for an off-kilter pairing, while the matching printed tops and long flounced skirts had a bohemian mien. Overall, Som seemed to be testing various ways of approaching cool, like a cat stalking tricky prey—a little street-y cool, a little retro cool, a little ragtag cool, a little hippie cool. To his credit, the clothes worked. Assiduousness goes a long way.

Anyway, Som wasn't really trying to do cool. He was trying do cool enough—to conjure just enough of a demimonde mood to satisfy a clientele comprising women who live uptown but who don't necessarily want to look like they do. As he said backstage after the show, he saw this collection as "Courtney Astor meets Courtney Love." That's not to say they met halfway. Most of this show was dedicated to oh-so-sweet looks—lots of floral, a bit of lace, a dappling of crystal. Even the cropped bustiers came off rather prim, which was a nice thing, actually. Yes, much of this stuff was a touch Louis Vuitton Spring '12, but for women who want to look pretty, that aesthetic will continue to resonate. Likewise, the tropical vibe of some of the clothes seemed like a bit of a retread. But as those killer board shorts show, Som is moving forward, with all deliberate speed.