Jeans and T-Shirts
Ever noticed the most powerful people in the world don’t really dress like it?
They’re not donning designer tuxedos or strutting around in high heels. They’re just there. Doing what they do, wearing the same thing every day. Yet these are the names that keep reshaping our world. The ones who actually have power don’t need to project it with clothes.
Look at Bill Gates. He was never a ‘suit guy’ in his early years. Today, the world’s more familiar with him in a sweater than a sharply tailored jacket. When you’ve built Microsoft, the outfit isn’t really the statement. It’s just a vehicle. Then there’s Mark Zuckerberg, one of the least fashionable billionaires in history. He wears the same thing daily: a grey T-shirt and jeans. His closet probably looks like the fashion equivalent of a factory line. Why? Because he doesn’t care. It’s functional. The uniform is just a tool, something that frees his mind for what matters.
Yet Vogue and The Rake will have you thinking style is the endgame. Style can be an asset, sure. But for real movers and shakers, it’s just not a priority. Success for them isn’t defined by the cut of their jacket but by what they’re doing.
Take Yohji Yamamoto, the Japanese designer born in 1943. Yamamoto has built his empire by sticking to his basics, blending traditional Japanese aesthetics with a modern edge. His look is understated but iconic. Always in black, he’s practically a shadow. And yet, he’s one of the most revered designers globally, precisely because he lets his work do the talking. His clothes stand out without screaming; they’re not flashy, but they have weight. Like Yamamoto himself, who speaks softly but commands respect.
Then there’s Bill Cunningham. The man was like a fashion monk, snapping candid shots of the truly stylish as they walked the streets. He wasn’t after glamour. He documented people with real style—those who owned what they wore, whether it was haute couture or a plain suit. But even the stylish ones Cunningham captured were often ‘successful’ in projecting an image rather than genuinely building something.
The ones who build, they’re a different breed. Look at Musk. He’s in the factory, getting his hands dirty, wearing whatever gets the job done. Bezos, too. They’re not trying to impress you; they’re trying to solve problems. And that mindset often means they dress for efficiency, not admiration.
But here’s the paradox. These billionaires? They want their kids to live a better life. They work hard to create a world where the next generation can have everything. And, perhaps because of that, their children end up dressing well, polished, primped. But here’s the catch: they rarely have that drive. Musk and Bezos’ suits may be rare, but their ideas are relentless. Comfort is their style, substance over form.
For women, the stakes are different. An unspoken rule, if you’ll forgive the generalization: attractive women tend to dress up. Even in basics, there’s a deliberateness that speaks to an image. But look closely, and many of them have their favorites, those pieces they wear when nobody’s watching. It’s not about impressing; it’s about ease.
The bottom line for any entrepreneur, for any creative? You don’t need to dress up to get ahead. In fact, it might be a disadvantage. Because the more you focus on image, the less you focus on building, on creating, on solving.
Success isn’t about standing out; it’s about showing up.
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Copyright Stephen Bray 2025