This semi-casual combo of a brown shearling jacket and a navy crew-neck sweater is very easy to throw together without a second thought, helping you look seriously stylish and ready for anything without spending a ton of time combing through your wardrobe. For times when this outfit is too much, tone it down by slipping into a pair of grey athletic shoes. This combination proves that as an over-50 man, you still have a wide array of outfit options.