This menswear style with a brown shirt jacket and a dress shirt isn't so hard to pull off and easy to adapt. To add a hint of stylish nonchalance to your outfit, introduce a pair of dark brown leather brogue boots to your ensemble. During the winter months, when warmth is key, it can be easy to settle for a less-than-stylish ensemble in the name of functionality. This ensemble, however, is a good illustration that you can actually stay toasty and remain equally stylish in the winter months. When it comes to dressing ideas for over-30 men, this outfit looks cool on most guys.