Opt for a red and black gingham long sleeve shirt and black skinny jeans for a relaxed casual ensemble with a city style finish. Feeling venturesome today? Shake things up with a pair of tan leather casual boots. Planning a pulled together look can be a bit nerve-racking and time consuming on its own. Add uncomfortably cold temps into the equation, and the whole thing becomes even more difficult. Don't despair, this here is your wintry outfit inspiration.