Uber dapper and comfortable, this relaxed combo of a blazer and a henley shirt will provide you with excellent styling possibilities. Why not take a more relaxed approach with shoes and complement your look with white leather low top sneakers? When you have one of those gloomy fall days, sometimes only a killer outfit like this one can get you to face the outside world. A perfect getup to make you a dapper man in his 40s, rather than just a man in his 40s.