This pairing of a grey crew-neck t-shirt and black skinny jeans is on the casual side yet it's also sharp and truly stylish. Black leather double monks are a fail-safe way to infuse an added touch of style into this ensemble. During the winter months, when warmth is prized, it can be easy to settle for a less-than-stylish outfit in the name of functionality. But this outfit is hard proof that you can actually stay comfortable and remain stylish in the winter months. After fashion for guys in their thirties? This pairing is great inspo.