Facebook founder Mark Zuckerberg can afford to dress down, even when he’s courting Wall Street suits. But what are the rules for the rest of us?

Tom Lamont Let’s break this in two. Should Mark Zuckerberg (who earlier this month upset potential Facebook investors by attending a meeting in casual clothing) do business in a hoodie? Absolutely. The founder of a society-altering business, the de facto president of an online nation-state with a population exceeding Europe’s, should do business in any clothes he wants. In his underpants, if the fancy strikes. In yours.

But should I, or you, or anyone else below Zuckerberg’s level of important-enough-to-act-with-impunity do business in a hoodie? Well, sure. Within reason there ought to be the freedom, in all forms of professional life, to dress in which ever way you feel you’ll work best. This is at the root of Zuckerberg’s admirable commitment to gymwear, surely. He did the early graft on the $100bn-valued Facebook while snug in a $30 hoodie from Gap, and at no point, as he watched his business grow, did it seem sensible to change out of comfortable clothes.

I work better in a jumper than a jacket, too. A suit isn’t comfortable to me, it doesn’t make me feel confident or capable, and just as importantly I don’t feel I’ve got the time or the spare loot to buy and then maintain a formal wardrobe. I don’t see why fusty tradition, principally upheld by the FTSE-Ferrari crowd, should insist on it as the professional norm.

Alex Preston I hate Mark Zuckerberg. I also hate the late Steve Jobs (hated? No, the hate’s still there). I don’t hate them specifically for their wardrobe choices: the casual grey hoodie, the Spirit of ’68 black polo neck. But their attire says a great deal about them. They are both what Slavoj Žižek would call “Liberal communists”: counter-culture geeks who take over big corporations. By dressing as they would in their free time, they seek to destroy the traditional boundaries between work and leisure. Zuckerberg’s hoodie marks him out as a denizen of the 24-hour mobile office, a globalised work-machine interfacing via his BlackBerry and iPhone with the world’s markets. He doesn’t wear a suit because suits can be taken off. Zuckerberg is still a CEO in his pyjamas, still CEO at 3am on a Sunday morning, still a CEO when drinking with Justin Timberlake at a disco (I may have mangled fact and fiction there…)

I have no wish to dictate what you wear to the office, Tom. And one can imagine the donnybrook that would ensue were the Observer to insist on suits and ties. But not all are lucky enough to work within the light-filled halls of a thriving media empire. Uniforms can be a carapace, a way of getting through the day. For most of the world, work is a five-day slog bookended by brief bright weekends with loved ones. Being able to pull on a uniform – whether that’s a suit, overalls or a white coat – helps people distinguish between who they are at work and at home or with friends. This is important, and I know I appreciated it when I had a job I loathed.

And one more thing: the hoodie Zuckerberg was wearing wasn’t from Gap. Embossed upon it in oh-so-subtle slightly darker grey was an advert for Facebook. Even in his dressing down he is ever the corporate man.

TL The noisiest complaints about Zuckerberg’s hoodie came from Wall Street figures who felt his outfit showed “immaturity” and (crucially) not enough respect for the wealthy businessmen who attended his meeting. Bit off, I think, for you to bring smocks and overalls into the equation, as if corporate suits were only another type of necessary professional uniform. Formal tailoring is one of those petty elitist ways that those in big-money jobs tell us and each other how well they’re doing. In Dickens’s day businessmen ate themselves fat to flaunt success. For a while, though, it’s been a case of getting down to Zegna to buy whatever virgin-wool pinstripe is on the inside cover of How to Spend It.

I loved that Jobs never wore a suit, and it gives me great pleasure now to think of the bafflement of the “dress for success” types when they consider Apple and Facebook, soaring despite being bossed by men who couldn’t give a shit how many ticket pockets you’ve got in your two-piece.

The Observer is brilliantly, admirably non-restrictive about employee attire, and I’m lucky to be relatively free to dress myself of a morning. I’m tall and skinny, and on the rare occasions I have to wear formal clothes I’m never quite at ease (like a footballer inspecting the pitch on FA cup final day). It’s a privilege to be able to choose, and it could only be a good thing – not the flummoxing burden you suggest – if such a relaxed attitude extended into other areas of work and business.

AP I felt justified calling on those other professions, Tom, because the heft of your argument seems to rest on what you wear to your job at the Observer – hardly a hotbed of corporatism (or is it?). We all know that journalists are a slovenly bunch, and I’m sure no eyebrows would be raised were you to turn up at your desk in egg-stained Y-fronts and a fuchsia foulard. But I’d hazard a guess that if you had a meeting with your editor to “map out your career trajectory”, or if you were called on to interview an MP at the House of Commons, or the Archbishop of Canterbury at Lambeth Palace, you might pause before the wardrobe in the morning. And this is because what we choose to wear sends a clear message to the person we are meeting with.

Zuckerberg’s hipster attire is an eloquent statement of his disregard for those on whom his business’s continued expansion relies. On this, a red-letter day for his blue-logoed company, when he was turning up cap in hand and asking a group of professional investors to trust him that Facebook was worth its (ludicrous) $104bn valuation, his choice of dress was a sign of arrogance, a condescending reminder to the money-men that he isn’t one of them (except, of course, we all know he is). I’m leaning on rather old-fashioned concepts of respect and good manners here, and the fact that his investors are, as you point out, Wall Street monsters who eat boiled babies for breakfast should win the day for your pro-scruffy stance. But if I’m giving a lecture or a reading I’ll wear a jacket. I might even wear a tie. I’ll choose to dress in a way that conveys to the audience my regard for them, my thanks that, of all the things they might have been doing that day, they chose to come and listen to me.

Clothes are a highly complex system of signs and symbols, our most sophisticated means of sending messages about ourselves to the world around us. You may think it strange that anyone still cares about what we wear, but people do. By choosing to address a formal audience in informal dress, we not only risk making them feel foolish; we say to them that we don’t care about their values, about the conventions of the world they inhabit. It feels contemptuous and presumptuous and unpleasant. I’m not saying everyone should wear a suit to work every day of the week – I’m merely suggesting that we should think carefully about what our choice of clothing says about us and our regard for others.