We don’t really have any documentation that mentions for certain as to when Dyl began his affinity with the Boston Red Sox team and began to wear the “B” ball cap. Dylan played Little League as a kid, and apparently played very hard and competitively to win and when his team didn’t or he had to sit out, he was crushed. This demonstrates his extreme love and passion for the sport and being dedicated to his team winning as if the weight of it depended solely upon himself. I would imagine he would’ve begun to start collecting Baseball cards at a certain point in Elementary school and resonating with certain players while watching them on tv or going to a game with his dad. So, I’m going to say he probably got his first official Boston Red Sox ball cap in his latter Elementary school years and wore that ‘first’ hat through middle school until it was ratty and tattered. Rather than chuck the entire hat and get a new one, his insisted tradition and solution seemed to become him selecting a new replacement hat (with another team he liked) and having mom sew the “B” on the ‘back’ of the new hat. The “B” itself was the totem, his lucky piece, you could say? It reminded him of personal ‘happy time’ past memories. There is a certain sentimentality about Dylan in regards to keeping certain personally significant touchstone items with him throughout his life, on his being, that remind him of a certain something in his past. I go into detail about this
idiosyncrasy of his “B” baseball cap here.
Dylan does wear his signature baseball cap forward in this shot which appears to be circa early middle school years – playing drums in a band with Brooks Brown. At some point in the ‘90s, the anti-fashion became about wearing the ball caps backwards to look more against-the-grain of mainstream style.
I think he likely shot up in height quite noticeably between his Freshman to Sophomore years. My guess.













