[djcapelis]

> So he meets the people he's going to work with: his "boss" is in a stained t-shirt, shorts, no shoes, super casual. I mean like 20 years ago he wouldn't have been able to buy a soda in a beach-town convenience store.

No wonder everyone's nervous around your friend. If he forms his opinions on whether or not his manager has authority based on his clothing that's going to be an inheriently uncomfortable experience. Why did you use scare quotes around boss? And would you do it if the guy had worn nicer clothing?

Does your friend feel that way?

If so, his new co-workers are right to be nervous. The fellow is seriously misaligned in understanding how his new workplace is structured. He can dress how he likes, but if he starts using clothing to measure respect in a modern workplace... that's a problem.