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When musician Ezra Koenig gets the urge to shop, he doesn’t go to Rodeo Drive or any of the Sunset Boulevard boutiques catering to sharp dressers like him. Instead, the Vampire Weekend singer heads to Macy’s in the Beverly Center. “I like to see what’s going on with Polo,” said Mr. Koenig, 33. Years ago, as a New Jersey ’tween, he was initiated into the religion of clothes by the Ralph Lauren brand and he remains a fairly devout follower.

That shouldn’t surprise his own worshipful fans. Ever since 2006, when the indie-pop…