Fall always inspires me to go shopping. Of course I need new coats, cardigans and the latest pair of boots for the season. But I also need my annual dose of plaid. I’m a fan of all plaids, but the bold black and white buffalo plaid is my signature. And who does plaid better than Steven Alan? That’s why I’m obsessed with this Steven Alan checkered boyfriend shirt ($158; stevenalan.com). The over-sized cut not only makes me feel small and cozy in the cool fall weather, it looks downtown-chic when belted and worn with leggings and platform booties. Or if I want to go a bit retro and 90s-grunge-cool, I pair with ultra-worn jeans and vintage Dr. Martens boots. How would you wear it?