For a casual outfit with a modern spin, opt for a white and navy long sleeve t-shirt and jeans. You can get a little creative with footwear and elevate your outfit by rounding off with a pair of tan suede casual boots. If it's one of those dreary autumn afternoons, what better to cheer it up than a stylish ensemble like this one? A safe bet pairing appropriate for over-50 gentlemen who like casual dressing.