I think shirt dresses are supremely cute. If you know me, you know that I am a firm believer that menswear on a woman feminizes her image even more–explaining my propensity (fetish?) for wearing only mens’ watches. Right now it’s a Stuhrling Original, if you’re curious. But I think the key to pulling off the shirt dress, which is characteristically lacking a waist (men don’t really have much of one, you see) is to cinch it with a tie, ribbon, or (my fave) a belt. Pair it with some tights or go bare-legged and crazy–just make sure they’re heels you’re wearing. Oxfords could be overkill.