Channel your inner Bond and dress in a beige overcoat and charcoal wool dress pants. Brown leather loafers are guaranteed to give a sense of stylish casualness to your look. As you can see, it's super easy to look seriously stylish and stay toasty when chillier weather comes, thanks to this outfit. So if you're on the lookout for style tips on how to dress as you head into your 50s, this outfit is ideal.