Here, the casually classic style translates to a brown plaid blazer and brown chinos. For something more on the sophisticated side to complete your look, add a pair of brown leather tassel loafers to the equation. Can you see how very easy it is to look seriously stylish and stay toasty when chillier weather hits, thanks to this outfit? A look like this will help any 50-year-old guy upstage his younger fellows.