To look great and dapper, wear a blue wool blazer and grey dress pants. When it comes to shoes, this look pairs brilliantly with dark brown suede loafers. In winter, when practicality is imperative, it can be easy to settle for a less-than-stylish getup. However, this getup is a bright example that you totally can stay warm and remain stylish during winter. Overall, a never-failing option when it comes to outfit ideas for 30-something Millennial guys.