With a little help from Miuccia Prada (and some dude named Paul Mescal), the perennial cool-girl staple has crossed over to ...

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.

Sam Parven, a 26-year-old in D.C., considers dressing like an old man the ultimate style move. The advertising exec looks sharp in pleated pants, sweater ... The look—cardigans, high-waisted ...