Kickin' it New School

While on my lunch break yesterday I was walking on the PATH below my building. I always see weird things down there, but only in that particular junction between Queen Station and the Eaton Centre. What I saw yesterday was not quite strange, although it was entirely unique. There was a man walking from The Bay into the mall carrying an open laptop on his shoulder like an old boombox. Old school hip hop was blaring from its weak-ass speakers and he probably could have benefited from this:One of the things I found interesting about the guy was that he was dressed business-casual and didn't look like he would be spending his lunch break doing anything but heating up last night's leftovers in the office microwave, yet his swagger injected some colour into an otherwise stuffy PATH system. Awesome.
Now, some things I would like to know are:
Did he walk out of the office like that?
Does his boss know that he uses a loaner computer to get down on his way to the food court?
Are there gold chains buried below his baggy button-down shirt? And if so, does he purposefully wear poorly fitted clothing so that he can fit all his gold chains under his office attire?
When the person at the desk next to him asks him how lunch was, how will he respond?
Hmmm...