For a casually stylish getup, dress in a navy shirt jacket and beige chinos — these two items fit nicely together. Finishing with grey athletic shoes is an easy way to infuse a more laid-back vibe into your look. As you can see, it's extremely easy to look stylish and stay comfy when chillier days are here, all thanks to combos like this. Guys wondering how to stay fashionable as you move into your 50s, you have your answer.