For an outfit that's truly envy-worthy, wear a military jacket with a turtleneck. Dial up the dressiness of your look a bit by finishing with a pair of brown leather derby shoes. There's no better way to spice up a dull autumn day than a kick-ass look like this one. As you're progressing through your late 20s, you want to start dressing like an adult man. In this case, combos like this are a solid bet.