For a laid-back and cool ensemble, wear a navy varsity jacket and chinos — these two pieces fit perfectly well together. You can take a classic approach with shoes and complete this look with a pair of black leather loafers. Piecing together a pulled together look can be a bit of a juggling act on its own. Add extra cold temps into the equation, and the whole thing becomes even more difficult. Fear not, this here is your winter outfit inspo. Now that's how you do semi-casual as an over-40 gentleman.