Photo: Phil Oh

Maybe it's the New Yorker in me, but I like to dress up. Even when I know I'll be at home all day in front of my computer, I will still get "dressed." So, when I wear jeans--the epitome of casual in my mind (and not to sound obnoxious, but sweats and fleece are not in my style lexicon, unless I'm working out)-- I tend to pair them with something unexpected and fancier on top. This picture represents how I'd dress up jeans for, say, a dinner out with girlfriends: with a pair of Isabel Marant heels, a feminine lacy top and a tuxedo blazer. The look is polished and cool. And exceedingly comfortable too.