Sensible option: Hawkings McGill, $59 
Splurge option: Grenson, $430 
Why dad needs it: If you're proud of your father for all that he's achieved so far, then help him go one step further and stunt on all other dads by winning the footwear game. A pair of rich brown brogue shoes will go with whatever style he rocks on the daily, and will definitely up his steez beyond his peers who will be ashamed of their square-toes shoes and their wack sons.