I used to live and socialise in a place where a lot of my city's security guards and bouncers drank, and became if not friends, at least familiar with many of them. (Kings Cross in Sydney in the 80s/90s)
I also used to pretty much exclusively wear black jeans, black t-shirts and when it was cold enough a black leather bike jacket.
I would often show up to clubs or gigs, and just get waved in by whoever was on the door because that assumed I was arriving for work.
It was the middle part between the two bits you quoted - he was just going to a show, was in a phase where he liked wearing all black, and would get waved in without even intentionally trying to trick anyone because they assumed he was arriving for work. Does that help?