The shirt dress and me
So yes, I know, the boyfriend-shirt-as-a-dress look is kind of a love-it or hate-it trend, and I wasn't sure which way I was swaying until I met this one. The Layla Boyfriend Shirt from Two Feathers is extremely comfortable, and the high-low cut ensures that, while sexy, you aren't accidentally showing off your bum.
I paired it with my fave Report cut-out booties and feel like I can wear this look anywhere. I also love that unlike most dresses, you don't have to wear a jacket over it - the fabric and cut make it warm enough even for evenings (in San Francisco, anyway).