Make a black crew-neck t-shirt and blue skinny jeans your outfit choice for a casual street style ensemble that's also easy to wear. For a more refined finish, why not introduce a pair of grey leather casual boots to the equation? Can you see how very easy it is to look seriously stylish and stay comfy when cooler weather arrives, all thanks to outfits like this one? Relaxed casual combos for stylish gents in their fifties aren't actually that hard, as you see.