The dapper dude is all about old-school sophistication. This suave gentleman — think Don Draper from Mad Men — looks polished and refined on every occasion. For a college football game at his alma mater, he'll dress up his jeans with a blazer and plaid scarf. At dinner, he'll opt for slick loafers and decadent cuff links. Gift him with classically svelte items. My dapper dad would flip over this timeless Michael Kors Chronograph Gold Watch ($225).