For an effortlessly classic outfit, dress in a military jacket and a grey sweater vest — these two items work nicely together. Give a laid-back feel to your look by slipping into multi colored athletic shoes. As you can see here, it's extremely easy to look amazing and stay warm when chillier weather arrives, all thanks to combos like this. This outfit illustrates that moving from your 20s to your 30s is no reason to stop dressing casually.