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Back when I worked at a men's magazine, before I went freelance, there was a sort of low-level arms race between the editors over our wardrobes. We'd fuss over each others' new windowpane blazers and attempt to one-up each other with the Goodyear welts on our monkstraps. Showing up with a new jacket or pair of trousers was an exercise in anxiety: Would it pass muster? Or, worse, would no one notice at all? Suffice to say, I thought about what I wore to work a lot more when the office was not also my kitchen table. There was one guy on staff, however, who didn't get in on this game: Matt, the autos editor. This is because Matt wore the same thing every day. His wardrobe consisted of a pair of chinos in black or navy, a cotton button-down in blue or burgundy and a pair of desert boots. On fewer than five occasions I saw him add a blazer to this ensemble for formal events, but otherwise it did not change.

Some men wear a uniform because they have to. Others wear it because that's the only thing they ever want to put on. Matt is by no means alone in the latter category – he's in the company of software tycoons, heads of state and some of the world's most successful creatives. My closet is filled to bursting with shirts, jeans and blazers for every temperature, occasion and season. I've always enjoyed the process of picking an outfit in the morning: creative expression through fashion. Now that I work from home, however, I've found my regular rotation shrinking steadily. What if there's a better way?

"It's freeing," says Matt. He's a freelancer too now, but his wardrobe is unchanged. "Every day you get up and not think about what you're going to wear," he says. Matt is somewhat uncomfortable being the subject of a fashion story, because he sees his wardrobe as an entirely practical consideration: "If I had to think about what I was going to wear in the morning, not just what I'm going to do that day, it's another thing. What's the point?" On its most basic level, that's what uniform dressing is: ultimate wardrobe simplicity. Imagine how much time you'd save in the morning if you never had to think about what to wear, not to mention the time spent browsing, fitting and buying new items. Could this be the ultimate life hack?

Among the adherents to uniform dressing for practical reasons are Mark Zuckerberg (grey T-shirt, grey hoody, dark blue jeans) and Barack Obama (grey suit, blue suit), two guys known for being fairly clever. Neither of them are topping any best-dressed lists, sure, but it would also be fair to assume they have more important things on their minds than matching their ties to their jackets.

Uniform dressing is about streamlining and simplicity, but it's about style, too. Consider the uniforms of Steve Jobs and Karl Lagerfeld. Jobs's getup of black Issey Miyake turtlenecks (he claimed to have 100), light-wash Levis 501s and New Balance sneakers reflected his love of functionality and aesthetic purity. He was also dressing like a nineties dad years before anyone uttered the word "normcore." Lagerfeld, too, with his powdered white ponytail, fingerless gloves and fistfuls of jewellery, consistently dresses like a Roger Moore-era Bond villain, but nonetheless remains a style icon. These men were and are happy to wait for fashion to come to them, as it inevitably will. Wearing the same thing every day puts you above the ebb and flow of fashion, and for the people who create trends, that's exactly where they want to be.

"I wear a grey suit, usually in wool, white Oxford-cloth shirt, washed and dried but not pressed, grey tie with tie bar and black wingtip shoes," says Thom Browne, the designer whose eponymous label is credited with revitalizing men's suiting in the early aughts. "This is what I've pretty much worn always." Browne's trousers terminate just north of his bare ankles – his trademark length – but other than that he looks less like a fashion icon than a well put-together professional man. When I ask Browne about the advantages to dressing this way, his answer is frustratingly simple: "You don't have to think."

You do have to think, though. And the more I ruminate about Matt's wardrobe the more I begin to feel like I've never given him enough credit. Committing to a uniform is not the absence of planning, it's just the opposite. "You've got to put some thought into it, some research," he says. "You want only one pair of shoes? It's hard to find. You need a pair of shoes that can do everything."

I think of my shoe closet, a jumble of dress boots I wear once a year, brogues that give me blisters, and running shoes. I have no idea where to begin. The payoff of a simpler, streamlined yet stylish life is tantalizing. The only remaining question is: What to wear?

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