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Last week, Facebook said "Yes, please" to a $500-million infusion from Goldman Sachs, bringing the company's valuation to an estimated $50 billion. And what does the public face of a $50-billion company look like in 2011? A large, behoodied toddler named Mark Zuckerberg.

Now 26, the Facebook founder is no longer the Harvard undergrad depicted in The Social Network, but the film's aggressively uncool wardrobe of Adidas flip-flops and sweatsocks will forever be signature Zuckerberg. And in real life, the billionaire's most famous sartorial proclivity is the hoodie: Andy Samberg on Saturday Night Live need only pair it with an unblinking grin to affect his Zuckerberg impersonation.

The fact that Time's Man of the Year can dress in such an offhanded manner seems a poignant marker of change considering we have just passed the generally accepted 150th anniversary of the business suit. A recent celebratory piece in The Economist dates the suit's birth to the late 19th century, when the tailed morning jacket beloved by Beau Brummel was elbowed out of popularity in favour of the sportier "lounge suit." (The modern suit is also, thankfully, less groin-enhancing than Brummel's self-confident dandy friends preferred.) But variations on the business suit, with its roots in military garb and hunting wear, go back as far as the 17th century. As Cally Blackman writes in her book One Hundred Years of Menswear, "the suit is a machine for living in, close-fitting but comfortable armour, constantly revised and reinvented."

Reinvention is great – even if the truck-flap-sized lapels of the seventies may have been a misstep – but the essence of the suit is sameness. Stand still in the business district of any major city at lunchtime and behold the school of grey and navy fish swimming by, distinguishable only through careful scrutiny of material, detail – and attitude. The older men, with shoulder-squaring cuts in accordance with the suit's military heritage, exude social stature; they put the power in power suit. The awkward young initiates to the business world – well, often the suit wears them.

But in traditional commerce, the young ones must announce their aspirations with pinstripes and surgeon's cuffs; the suit is the "armour" worn for the battle of men's work. And to not wear it in the business arena is a meaningful gesture, a rejection of the suit's paternal authority and a whisper of the enduring insult: "He's a 'suit.' " Lawyers and bankers may be forever suit-bound, but, as power has changed shape in the Information Age, so has its wardrobe. When Apple CEO Steve Jobs, age 55, presented the iPhone 4, he wore a black mock turtleneck and jeans. Forbes's third-richest American, Oracle CEO Larry Ellison, in his 60s, has also gone mock during public addresses, which bodes the question: Is the mock turtleneck the Boomer hoodie?

Rejecting the suit means planting one's flag in the new economy, pledging allegiance to the – pardon the phrase – "creative class," wherein casual wear has its own kind of anti-authoritarian authority. Last year, the website Gawker reported on Microsoft's attempts to ape Jobs's famous underdressing by giving two of its geekier CEOs makeovers. Former "Chief Experience Officer" J Allard, considered the man behind Xbox, went from button-downs and a bald spot to a futuristic shaved head and a striped hoodie.

But Internet gurus weren't the intended audience for the sweatshirt. Champion manufactured the first hoodies in the 1930s to keep workers in the chilly warehouses of upstate New York from freezing. It became a sports staple soon after, famously soaked with sweat by Rocky Balboa in 1976. By the eighties, hip hop adopted the hoodie, with wannabe gangsters like Eminem exploiting its inherently ominous architecture: The raised hood achieved a "cobra" look, all the better for getting up to no good.

For decades, a hoodie has signified living outside the dominant class, a badge of street cred for skaters and graffiti artists. But edginess never stays on the edges too long: Designers Balenciaga and Rick Owens both showcased hoodie-influenced pieces, with hefty price tags, in their spring shows. That billionaire Zuckerberg is more of a Champion hoodie guy than a Balenciaga one may be a function of 20-something schlumpf or of an attempt to make his sudden success seem accidental. A hoodie is comforting and childlike – a grown-up Slanket. Wearing one keeps Zuckerberg firmly on the right side of adulthood.

But taking off the suit may also be a way of identifying with the Facebook masses. In this recovering economy, suits are worn for job interviews, not jobs. In the new film The Company Men, Ben Affleck's character loses his high-paying executive position and, in exchange, gets a few months at an out-placement centre. On his first day of the job hunt, he joins a room of fellow lay-offs sending out their résumés and hitting the phones. An unemployed engineer, scanning Affleck's grey, double-breasted wool armour, says: "Nice tie." Translation: "Hey, Suit, you won't be needing that in here. How about a hoodie?"

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