For laid-back sophistication with a masculine twist, you can go for a black sweater vest and light blue jeans. Feeling transgressive? Play down this look by finishing off with a pair of dark brown suede desert boots. Can you see how super easy it is to look sharp and stay cozy when chillier weather comes, all thanks to combinations like this one? This ensemble is the perfect answer to the question of how to dress age-appropriately as you get older.