Back to that bit of irony, many of the merch baseball caps are just that. Take, for instance, the Filson caps created in collaboration with Ray’s Bar on the Lower East Side.

AMI Wool Cap, $110, Opening Ceremony, 646-695-5680; Cashmere Baseball Cap, $330, Brunello Cucinelli, 212-627-9202; Gents Cashmere Cap, $75, nordstrom.com ILLUSTRATION: Danny Kim for The Wall ...

The Major League Baseball playoffs are underway, and it’s time to get your ball cap on. These days, fans can support their team with caps in a variety of colors and fashions.

That means hats have once again become a semiological minefield. There is, however, a middle ground. “My advice,” said Stephen Jones, the British hat maestro, “would be to try a bucket hat.

"Back in '96, Spike Lee called and asked us to make him the Yankees baseball cap in red," says Chris Koch, CEO of New Era. "That moment started the fashion, street culture side of our business.