Try teaming a black overcoat with black wool dress pants to look good and stylish. Add a pair of burgundy leather casual boots to this look to bring an element of stylish nonchalance to this outfit. Keep this combo in mind when spring sets it, and we promise you'll save a ton of time getting ready on more than one occasion. This ensemble demonstrates that figuring out how to dress stylishly as a middle-aged guy is not that hard.