In Porter Square, I met David, “never Dave,” a longtime on-and-off-again local, reluctant fashion commentator and perhaps the most insightful dresser I’ve spoken with this week.
“I wouldn’t call myself fashionable,” he admitted. “But then again, not many people here would.”
David has lived in, outside and around Cambridge for 15 years. To him, the city’s style is fairly basic, though he clarified quickly that’s not an insult, just an observation. “Some people here dress with a strong sense of self, and I appreciate that. Others copy those people. I call them the second tier of Cantabrigians.” Harvard students, he says, make up a third tier, dressed in what he calls preapproved campus wear, a silent agreement of dress on campus.
His favorite group, though, is the fourth. “People like me – sometimes I try hard, sometimes I don’t try at all. I wear what feels right. Blame it on my contrarian youth. It stuck.”
David doesn’t shop much in Cambridge, aside from a recent pair of Ray-Bans from Harvard Square. “Does shopping in my family’s wardrobe count?” he asked, showing off his T-shirt from his uncle. “It fits me better than it fit him anyway.”
Sometimes, the best store isn’t a storefront at all. It’s someone else’s closet, especially when it belongs to family. There’s something effortless about borrowing from someone who shares not just your proportions but also your sensibilities. Style passed down from a relative can carry more than just good fabric: It carries values, memories and a sense of continuity. In a city such as Cambridge, where fashion is often more functional than flashy, those inherited pieces can feel the most authentic.
The fashion here might not always turn heads, but it tells stories of practicality, play, resistance and reinvention. The city wears a layered look, from Harvard polish to thrifted charm, from studied indifference to earnest expression. And sometimes it’s just a guy headed to a workout in his uncle’s shirt, living his style without overthinking it.
A stronger
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