A harrington jacket and a blue long sleeve shirt will convey this relaxed and dapper vibe. Want to tone it down with shoes? Add a pair of brown leather work boots to the mix for the day. As you can see here, it's extremely easy to look seriously stylish and stay toasty when colder weather arrives, all thanks to ensembles like this. This pairing illustrates that as a gent in his 50s, you still have a wide range of dressing options.