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.

With over a decade of experience as a designer, Tyler the Creator, brings a refreshing style perspective to the fashion world ... and the Pearl Cardigan ($595). Gold le Fluer coats ($1,050 ...

Staley sported a silver Louis Vuitton jacket along with logo sneakers from the label’s recent collaboration with rapper Tyler, the Creator. She also added on a pair of black sweatpants and ...