This laid-back pairing of a crew-neck t-shirt and navy sweatpants is a real life saver when you need to look stylish in a flash. Finishing off with white low top sneakers is a simple way to bring some extra definition to your look. In the winter months, when comfort is key, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. However, this ensemble is a shining example that you can actually stay comfy and remain stylish in the winter months. Guys who are curious how to sport cool off-duty dressing in your thirties, you have your answer.