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.

They’re more than just a tool for telling time; they’re a statement of style. In an age where technology dominates, the grandpa watch offers a refreshing return to simplicity. It’s a ...

“It’s really cool.” “Grandpa style has really taken over,” said London stylist Holly White. The look—cardigans, high-waisted pants, corduroys and anything else Mister Rogers might ...