For a cool and casual outfit, go for a grey sweatshirt and blue jeans — these pieces play really well together. A pair of black leather ankle boots instantly revs up the style factor of any outfit. During the colder months, when warmth is imperative, it can be easy to settle for a less-than-stylish look in the name of practicality. However, this look is a good illustration that you totally can stay cozy and remain seriously chic in the colder months.