Consider wearing a black overcoat and black dress pants for extra dapper attire. Feeling brave? Mix things up a bit by slipping into dark brown suede loafers. During the colder months, when comfort is top priority, it can be easy to settle for a less-than-stylish outfit in the name of practicality. But this outfit is a striking illustration that you can actually stay cozy and remain equally stylish in the colder months. If you're wondering what you should wear as a 30-something Millennial man, this combo is a good source of inspiration.