A charcoal wool blazer and blue jeans are a great pairing to add to your daily casual repertoire. Complete this outfit with white canvas low top sneakers to immediately amp up the appeal of this outfit. So as you can see, it's super easy to look seriously stylish and stay toasty come chillier weather, all thanks to combinations like this one. Casual getups for stylish 50-something men aren't actually that hard, as you see here.