His fitted hat, also known as a baseball cap, from Loro Piana offered the right mix of sporty and stylish, becoming a core characteristic of the quiet luxury trend that overtook the fashion industry.

As the New York Yankees and Los Angeles Dodgers meet in the World Series, it’s not just a matchup of the teams with the most American League and National League pennants, respectively.

“The Dodgers cap became a representation of the West Coast. It’s evolved from being a piece of LA to representing an entire ...