Bros to Men: Tech Founders Are Finally Dressing the Part

Since the dawn of the iPhone roughly two decades ago, the fashion of tech founders has been defined by, well, a lack of it. Silicon Valley’s anti-style staples are easy to recognize: the worn hoodie; the scuffed sneakers; the casual, sometimes sloppy, brand of effortlessness projected by the ruling class of mostly male tech elites. It is the uniform worn by someone whose attention is anywhere but on their wardrobe. “There was this perception of, like, ‘I just don’t care,’” says Arati Sharma, an early Shopify employee turned entrepreneur and investor. “‘I’m too busy running my company.’”

The origins of this look can be traced back to Mark Zuckerberg in the early days of Facebook. A few years after launching the website, he famously appeared in a CNN interview wearing a graphic tee, faded jeans and Adidas slides. Dressing down became synonymous with the grind of start-up culture, and when the company (now Meta) took off, so did the notion that you no longer needed to wear a suit to get things done.

And yet, at Toronto Tech Week, one of Canada’s biggest industry events, the picture couldn’t have looked more different. Our country’s most prominent leaders showed up looking surprisingly dapper. The customary garb of $20 Costco tees had been replaced with finds from the menswear category at Ssense. Michael Katchen of Wealthsimple wore what appeared to be a knit polo from Rag & Bone, Aidan Gomez of Cohere was in sleek Salomon performance sneakers and Mike Murchison of Ada wore a preppy pair of suede Grenson Peter loafers. Even those who were once staunchly against fashion seemed to have come around to the transformative power of a Brunello Cucinelli sweater. Founders are suddenly dressing like grown-ups again. What happened?

For one thing, Canada’s tech industry is coming of age: Just last year, an analysis by The Globe and Mail found that at least 71 technology and technology-enabled companies had passed a US$100-million revenue milestone. And as Canadian tech leaders are scaling up their ambitions, their clothes are following suit.

It’s an exciting shift in an industry where stylishness is adopted only after credibility has been earned. Most entrepreneurs trying to get a company off the ground are “eating from a cereal box,” says Eva Lau, a founding partner of venture fund Two Small Fish. In the early days, a laid-back look could even give founders a leg up, signalling to competitors that they play by their own rules and to investors that they’re thrifty with money. But peek inside the closets of founders who are further along in their start-up journey and you’re likely to find high-end brands like Patrick Assaraf and Loro Piana.

There’s a newly minted term for this phenomenon: the “tech bro glow-up”—and Zuckerberg is, once again, leading the charge. Back in January, he made headlines after addressing Meta’s more than three billion users wearing a million-dollar Swiss watch and a custom gold chain.

Through clothes, founders can (and do) flaunt their wealth (not always advised) or communicate their vision—onstage, in meetings and in the media. While respect in the industry is still earned by what you’ve done rather than what you’re wearing, Christian Weedbrook, the founder and CEO of Xanadu, one of the world’s leading quantum-computing companies, says there are benefits to being more visible as a founder, particularly when it comes to raising money and hiring talent. “I’ve always resisted it,” he says, “but I’m starting to change.” For a recent TV appearance, Weedbrook paired his signature black T-shirt from Banana Republic with a fitted bomber from Sandro.

Jack Newton, the founder and CEO of Clio, a legal tech firm, says his personal style has tracked with the company’s nearly-20-year trajectory from a scrappy start-up to one of Canada’s highest-valued tech firms. “There’s been more of a spotlight on Clio and myself over the past few years,” he says, likely referring to a recent string of successes, including securing $1.24 billion in funding, valuing the company at more than $4 billion. When Newton started the company, not wearing a suit was a “nonconformist act of rebellion” for a new start-up in a traditional industry. But now, the growth of Clio has nudged him toward a more refined, professional look—though with a casual vibe. This is still tech, after all.

As our country’s disruptors and billionaires-to-be continue their path toward the top of the global tech stratosphere—and spend more of their career in the public eye—they’re likely to refine their fashion choices even further.

“Maybe it’s just a reflection of the old maxim ‘Dress for the job you want, not the job you have,’” says Newton. This writer would suggest drawing the line at Zuck-inspired chains, though.

This article first appeared in FASHION’s October 2025 issue. Find out more here.