This casual pairing of a windbreaker and grey sweatpants is super easy to pull together without a second thought, helping you look on-trend and ready for anything without spending a ton of time rummaging through your closet. A pair of black athletic shoes effortlessly revs up the street cred of this outfit. As you can see here, it's very easy to look amazing and stay cozy when chillier weather arrives, thanks to this outfit.