Last month, two very striking men took to the stage of a Toronto hotel ballroom filled with entrepreneurs.
In one chair sat Difference Capital CEO and new Dragons’ Den star Michael Wekerle, looking every inch the rock-star mogul, in an impeccably tailored black jacket (complete with tails) and expensive-looking grey leather shoes. In the other sat Harley Finkelstein, who, as chief platform officer of Shopify, is helping to lead one of Canada’s most exciting companies. Twenty years Wek’s junior, he wore the new-economy uniform of a simple black T-shirt and jeans.
Neither Wekerle nor Finkelstein (who were conducting the keynote interview at the PROFIT Growth Summit) fits the traditional mould of what a successful business person is supposed to look like. But Finkelstein embodies a growing trend—one that just might upset the con- ventions that supported a mil- lion corner-office careers. Maybe it’s no longer necessary for ambitious leaders to “dress the part.” Maybe we really have entered an era in which ideas trump appearance. Maybe.
The list of brilliant entrepreneurs with a “who cares?” sartorial philosophy stretches from scruffy tie-dyed ice cream titans Jerry Greenfield and Ben Cohen to Steve Jobs in his mock turtlenecks and mom jeans. In large swaths of the tech industry, every day has been Casual Friday for the past two decades. “We believe one can be serious and productive without a suit,” Google spokesperson Jordan Newman told Bloomberg in 2010.
The trend peaked in 2012, when Mark Zuckerberg chose to wear a hoodie and a T-shirt when promoting Facebook’s IPO. At the time, Zuckerberg’s schlubby style spurred nearly as many headlines as his company’s bold valu- ation. Tech blogger Om Malik called Zuckerberg’s appearance a “fashion abomination”; Wedbush Securities analyst Michael Pachter dubbed it a “mark of immaturity.”
But for every suit who tut-tutted Zuckerberg’s getup as silly or disrespectful, there was a bright-eyed up-and-comer who saw it as revelatory. In the past two and a half years, what was once a symbol of dot-com cheek has become—for swelling masses of (mostly) male, (mostly) Millennial workers in all sectors, not just tech—a perfectly acceptable way to dress for work. There’s now a whole generation of ambitious young business leaders who wear the same clothes to pitch an investor as they do to play a game of ultimate Frisbee.
For them, people like Zuckerberg (or tattooed Vice Media CEO Shane Smith or T-shirted Google CEO Larry Page or plaid-clad Hootsuite CEO Ryan Holmes) signal an intoxicating new era of leadership, one in which nothing—not appearance, not pedigree, not tenure—matters more than the quality of the work being done. It’s an idea that fits nicely into the current zeitgeist of progressive companies; as traditional organizations give way to flat hierarchies, choose-your-own-title meritocracies and no-office workspaces where the CEO shares a desk with the intern, spending time perfecting a Windsor knot or squeezing into pantyhose seems both archaic and superficial.
The problem is that the vast majority of string pullers in Canada still don’t think so, which is why it’s a mistake to think ultra-casual garb is any sort of ticket “in,” the Millennial equivalent to once-ubiquitous grey flannel suits and pencil skirts. The environment is less formal than it used to be, but many of the power brokers with real finance, law and purchasing clout still expect certain standards of professionalism from those they deal with. Show up in shower sandals if you like, but know that unless your idea is inspired or your track record is flawless, you’ll be laughed out of the boardroom.
Zuckerberg, Finkelstein and their über-relaxed allies can pull off the aesthetic because they do exceptional work. They achieve great results—from customers, investors and employees—not because of their wardrobes but in spite of them. It’s their business acumen, not their defiant style, that ought to be emulated. Nail that, and you can rock the Converse all you want.