For an effortlessly smart outfit, dress in a grey wool blazer and a light blue long sleeve shirt — these two items go perfectly together. Puzzled as to how to round off? Complement this look with a pair of dark brown suede desert boots to change things up a bit. Rest assured, this outfit will keep you cozy as well as looking sharp in this awkward fall weather. Dressing inspiration like this will help you remain incredibly stylish well into your 40s.