If you're on the lookout for a casual but also seriously stylish outfit, consider wearing a shirt jacket and a white and black crew-neck t-shirt. You can get a little creative with shoes and spruce up this outfit by rocking brown leather casual boots. So as you can see here, it's a kick-ass, not to mention season-appropriate, look to keep in your transitional sartorial collection. This one is a modern but also age-appropriate pairing for middle-aged men.