Michael Andrews says he got the inspiration to start his custom tailoring business as a corporate associate at King & Spalding. Wearing a suit and tie every day made him acutely aware of the drawbacks of mass-market tailoring. “I have an athletic build, but I wanted slim fit, and off the rack you only had boxy baggy stuff or stuff that was too slim fit for an athletic guy to squeeze into,” Andrews says, adding, “I really fell in love with the idea of custom-made clothes.”

A prelaw stint in the dot-com world had given him a taste for entrepreneurship; after taking courses at New York’s Fashion Institute of Technology, he launched Michael Andrews Bespoke in 2006 in New York. In some ways, he says, tailoring is not so different from being a lawyer. He’s still advising clients—on pattern and fit, not mergers and acquisitions—and trying to build long-term relationships. “Our goal is not to sell a guy one suit, but to sell him whatever he needs for the rest of his life,” he says.