If your dad is particularly stylish (or desperately trying to be), the obvious upgrade is in the accessories. New ties and socks are easy ways to show people that he's not just some schlubby old guy. Trading in his more expensive, classic watch in favor of something more modern and colorful is also a good way to do this. These Conway 38MM Watches ($298, Jack Spade) in red and in orange scream, "Hey guys, I may be old, but I'm still fun!," and perhaps most important to his young co-workers, he's got enough money to cover everyone's Happy Hour bar tab. What a cool guy!