Diego Della Valle

Occupation: CEO and President of Tod's 

In Rick Ross' "London Skit" off the Rich Forever mixtape, the narrator mentions a pair of "warm Tod's loafers," so you know this company already has street cred. With Diego Della Valle at the helm of the Italian leather goods manufacturer, he's a different sort of "bawse," albeit not a red-bottomed one. Shoemaking was the family business, so a job with Tod's wasn't too far-fetched. Noted for getting celebrities to co-sign the brand's famous driving moccassins, one of his best power moves was getting FIAT head and timeless style icon Gianni Agnelli to rock a pair of the shoes during Juventus soccer matches.