Marry a navy suit with a crew-neck t-shirt and you'll ooze masculine sophistication and class. A trendy pair of black leather tassel loafers is the simplest way to upgrade your outfit. During the winter season, when comfort is the priority, it can be easy to settle for a less-than-stylish outfit. But this outfit is a bright example that you can actually stay comfy and remain equally stylish in the winter season. Interested in dressing tips for 30-something Millennial guys? This outfit is worth saving to your inspiration folder.