I’m that guy who will buy one pair of black jeans, never wash them, wear them every day until they fall apart.” ...

I was a punk, not the popular kid-going to thrift stores, cutting things up, burning little teeny cigarette holes into things.' ...

There’s a knack to pulling off old-timey classics. Tips for younger guys and boomers about the items worth embracing—and what’s best left in the past.