For a laid-back and cool outfit, choose a crew-neck t-shirt and brown jeans — these two pieces fit pretty good together. Dark brown leather casual boots will infuse an added touch of polish into an otherwise all-too-common outfit. You're sure to always look stylish even despite the sweltering heat if you have this ensemble in your front hall closet. This combination illustrates how to keep succeeding in the casual style department as a middle-aged gentleman.