Sensible option: Rumba Time, $95 
Splurge option: Uniform Wares, $606 
Why dad needs it: If your dad taught you the important of punctuality, chivalry, and classic style, then it's time for you to give him a watch that is an update to the heirloom he carries on his wrist. Besides, this might make him one step closer to passing that rare antique timepiece down to you. Just sayin'...