Why not opt for a denim shirt and black jeans? These two items are very comfortable and will look awesome when teamed together. And if you wish to instantly up the style ante of this outfit with one item, why not add a pair of dark brown suede casual boots to the mix? During the winter months, when practicality is prized, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a striking example that you totally can stay cozy and remain equally stylish during the winter months. Relaxed getups for stylish 30-something guys aren't actually that hard, as you can see here.