For a tested semi-casual option, you can never go wrong with this combination of a dark brown overcoat and a light blue chambray long sleeve shirt. Feeling inventive today? Switch things up by finishing off with brown leather derby shoes. Can you see how very easy it is to look sharp and stay comfortable when chillier weather arrives, all thanks to ensembles like this? So if you need fashion tips on what to wear as you go into your 50s, this combination is definitely worth saving for later.