When it comes to dressing for chilly days, we—your WhoWhatWear.com team—know that comfort trumps cuteness. After all, it doesn't really matter how fabulous your outfit is if you're getting frostbite while wearing it, right? But don't fear that the frosty weather means you're doomed to looking like a complete tool! As you can see from the stylish winter wardrobe choices of ladies like Alexa Chung, Chloe Sevigny, and perpetual reader-favorite, Rachel Bilson, with some smart planning, you can look fashionable even when the forecast predicts bitter wind and brutal temperatures!

