This pairing of a crew-neck sweater and blue sweatpants is definitive proof that a safe off-duty outfit doesn't have to be boring. Tone down the classiness of this ensemble by slipping into a pair of white and black athletic shoes. As you can see, it's super easy to look on-trend and stay comfy when colder weather comes, thanks to this outfit. This outfit shows how to keep succeeding in casual dressing as a 30-something Millennial man.