8 - Will Wright
Cutting an aggressive 'man at Zara' dash in coordinating separates, the boffin behind SimCity and The Sims cleverly accessorizes with a look that echoes General Zod before he lasers you with his eyeballs. There's nothing middle about this guy's wear.
Same vibe, different pose. "I might be the boss", he's saying, "but prize apart these folded arms and you'll find an embrace as warm as Narnia is cold."
As we've learned before, erotic champions of the programming world are prone to sartorial faux-pas. Of course this was probably just bad advice from his stylist. But rarely do you see a fleecy-muscle-tabard and an experimental mono-sleeved trauma-harness worn together outside a Vivienne Westwood show. Brave.