Consider teaming a polo with grey sweatpants if you're scouting for a look idea for when you want to look casually cool. Take a dressier approach with shoes and complete your outfit with white low top sneakers. As you can see here, it's super easy to look awesome and stay cozy when chillier weather hits, thanks to this outfit. Wondering how to master casual looks as you head into your 50s? This combination is an amazing example.