For a look that delivers functionality and dapperness, wear a navy shirt jacket and blue jeans. If you want to break out of the mold a little, add black leather low top sneakers to the equation. Keep this combination ready to go when spring comes, and we guarantee you'll save a lot of time brainstorming for what to wear on more than one occasion. Wondering how you should dress as you step into your 60s? This pairing is the perfect answer.