Light Hearted

They run multibillion-dollar conglomerates, negotiate major deals, and are looked up to as bastions of power and influence. But when it comes to their wardrobes, many of the world’s top executives have some remarkably quirky dress codes they adhere to religiously.

Let’s start with the reigning king of CEOs who decided a decade ago that decision fatigue wasn’t a corporate philosophy he could subscribe to. Mark Zuckerberg’s life got exponentially better when he stopped having to decide whether to go with the vintage University of Phoenix t-shirt or the Duloc marathon participant one. “I really want to clear my life to make as few decisions as possible about anything except how to best serve this community,” Zuckerberg has said about his simple gray t-shirt uniform that lets him focus on the really important things – like deciding which privacy settings to remove next.

Then there’s Steve Jobs’ legacy – the viral turtleneck. Nobody quite knows why New Balances and a mock turtleneck screamed “visionary genius” to him. Maybe he wanted to be prepared to quit Silicon Valley at any moment to become a mall Santa. His biggest fashion contribution though – killing any thoughts of the turtleneck ever going out of style again. As Jobs put it, “That’s been one of my mantras — focus and simplicity. Simple can be harder than complex.”

The British luxury queen of giving zero you-know-whats, Anna Wintour, is rarely seen without her iconic bob and shades. It’s rumored her security team is trained to identify her purely by her hair bobbing around the corner before they see the rest of her. Her sunglasses, like the Queen’s purse, are deployed at precisely timed signals to convey critiques at runway shows. Models live in fear of the shades slowly lowering. However, Wintour insists her eccentric style is simply “my way of helping the designers I admire by showing off their workmanship.”

Speaking of power looks, former PepsiCo CEO Indra Nooyi rocked the sari and kurta like nobody’s business. She incorporated gorgeous traditional Indian designs into her professional wardrobe and showed the world pantsuits weren’t the only option for boardroom sass. As she once stated, “What I wear carries an important cultural message about who I am and where I came from.”

And let’s not forget those who wore their quirks more subtly, like Michael Eisner’s lucky Disney blazer, which he donned for every major deal during his tenure as CEO. Or Ralph Lauren’s accessorizing rituals which seemed more like sartorial handshakes with the universe before launches. Because what says “on top of my game” more than depending on the powers of a ratty old $5 foot-long necktie before major business deals?

Barack Obama has joked about his adherence to a personal uniform of gray or blue suits, saying “I’m trying to reduce the number of decisions I make per day.” Even Einstein quipped “If I had to choose how many seconds to waste on choosing clothes, it would be 0.”

At the end of the day, whether it’s Zuckerberg’s groutfit, Wintour’s shades, Obama’s power suiting or Einstein’s cringeworthy genetics professor meets P.I. get-up, these business tycoons have shown that the clothes don’t make the leader. But they sure do make them a lot more unique, relatable, and in some cases, unintentionally hilarious. And isn’t that what we all aim for in our personal brand? Being powerful and respected, yet approachable and memorable too? If that’s achieved through a deceptively simple uniform or quirky signature accessories, even the most elite can’t help but appear delightfully human and pragmatic.