Bennie sells discs at the disc golf course. Bennie is the guy who arranges timed skiing races up on the mountain. Bennie is just the placeholder of 'if you do this a lot locally, you know XYZ who is always around' and hence you are 'part of the scene' IE you have actually engaged with it on some level. Nowadays that might be substituted with 'do you watch XYZ streamer'.

The t-shirt didn't represent having a personality. It represented than 'I am around this community enough I have at least interacted with Bennie'. Someone wearing a Kmart t-shirt saying 'ah did you get that from Bennie' would be the exact cred/personality as having a Bennie shirt.