Consider teaming a charcoal wool suit with a white and red vertical striped dress shirt if you're aiming for a clean-cut, sharp outfit. For extra fashion points, complement your outfit with a pair of dark brown leather oxford shoes. When it comes to dressing for transitional weather, nothing beats a kick-ass getup that can take you from season to season. Wondering how you should dress as you age into your 50s? This getup is a great example.