The CEO who was told he’d never run American Express has made Amex cool again—and is beating JPMorgan, Visa, and the S&P 500

Stephen Squeri appeared to check all the boxes as the next CEO of American Express. By 2016 he had spent three decades at the credit card colossus, reshaped tech operations, headed the corporate and merchant franchises, and orchestrated a spectacularly successful restructuring. But the Queens, N.Y., native had a giant liability in his quest to succeed the crisply tailored, cuff-link-sporting Ken Chenault: He didn’t dress like a Wall Street CEO. A year or two earlier, Squeri had appeared at a board meeting, held during a New York Jets playoff game, wearing his lucky Curtis Martin jersey under a suit jacket as a “go get ’em” shout-out to his prized team. “Some directors were a bit put off,” he told Fortune. “People judged a book by its cover, and my cover wasn’t all that good.” Coworkers took notice as well. Years earlier, recalls Squeri, “one fellow manager asked me, ‘Where did you get that suit?’ and I said, ‘I’ve got five more just like it I bought for a couple hundred dollars, total.’” The colleague’s rejoinder: “Therein lies the problem.” As the board pondered Squeri’s qualifications, the head of HR advised him, “You need to dress like a CEO,” and proposed a solution: A clothing expert from a fancy store in Connecticut would come to Squeri’s New Jersey home on a Friday afternoon to orchestrate a sartorial reengineering. “The guy drives three hours in heavy traffic, and goes through my entire closet,” says Squeri. “And I say, ‘How much of this is going to work?’ and he says, ‘None of it.’” Squeri relates that the pair then spent hours picking out fabrics for shirts, suits, sports jackets, and overcoats, and selecting elegant shoes, socks, and belts. Before the haberdasher headed home, Squeri put a king’s ransom for the new wardrobe on his Amex card. The makeover helped get him the top job—and presaged the corporate makeover he has spent the past near decade enacting. Squeri has forged one of the top growth engines in financial services by luring lovers of luxe as