It sometimes seems like clothing can be one of two things - cute or comfortable. I often forgo comfort for the sake of an outfit, so when you find something that's BOTH of these things, jackpot.
A year or two ago I got on a weird wrap sweater vest kick. I actually have no idea if that's what you'd even call this - but I have several. They're delightfully warm and cozy like a giant blanket, but a fun pattern or cut makes them much more fashionable. It's like a chic Snuggie. Anyway, combined with some super soft leggings and fabulous boots, you've got an outfit appropriate for anything from airport security to cocktails with coworkers. If you're feeling ambitious, mix it with a studded belt or bright long sleeve tee. Or just add a pop of color with your jewelry - anything goes when you're wearing the fashionable snuggie.