Opt for a denim shirt and blue jeans for relaxed dressing with a modern twist. To add a little zing to this ensemble, complement your look with a pair of dark brown casual boots. In winter, when practicality is key, it can be easy to settle for a less-than-stylish ensemble in the name of convenience. However, this ensemble is a striking example that you totally can stay comfy and remain stylish in winter. This ensemble proves that even after fifty you still have a wide range of outfit options.