Alex Drexler Knows Where to Turn for Buttoned-Down Advice

In Personal Board of Directors, top business leaders talk about the people they turn to for advice, and how those people have shaped their perspective and helped them succeed. Previous installments from the series are here.

For Alex Drexler, it wasn’t always easy growing up with a famous, super successful father. “As a kid, I’d see his face on the cover of magazines,” Alex said of his dad Mickey Drexler, who, as CEO of Gap Inc. in the 1990s, made khakis and T-shirts cool. “The bar was set very high.”

So much so, that initially Alex wanted nothing to do with fashion. He worked as a bellman at several Ian Schrager hotels and, then, after graduating from Trinity College he enrolled in Cardozo School of Law with dreams of becoming a District Attorney and one day joining the Federal Bureau of Investigations. But law school wasn’t for him, and he dropped out after one semester.

Instead, he got a job with clothing brand Steven Alan, where he learned how to manufacture pants and blazers. “Fashion is in my blood and I couldn’t escape it,” Alex said.

He branched out on his own in 2012, when he opened Alex Mill, a clothing label that initially sold men’s shirts. He chose “Mill” for the name, because it stands for quality and the authenticity of making something.