How to ditch the suit and still look like a CEO

François-Henri Pinault, the chief executive of Kering, the French luxury conglomerate that owns Gucci, Saint Laurent and Brioni, wore a stretched-out zip-up hoodie. So did Mark Pincus, the founder of Zynga. Ron Meyer, vice chairman of NBCUniversal, wore a Mr. Rogers black cardigan and baggy black shorts. Ivanka Trump wore an oversize white shirt, untucked, and skinny jeans. Omid Kordestani, executive chairman of Twitter, wore a Patagonia puffer. Sheryl Sandberg, chief operating officer of Facebook, wore skinny cargo pants and a cardigan the color of dried mud.

These were some of the outfits modelled at that ultimate showcase of mogul leisure wear formally known as the Allen & Company Sun Valley Conference 2017 and more colloquially called "summer camp for billionaires." It may have ended Sunday, but its style preferences will resonate throughout the rest of the season.

If you want to know how to dress down like a power player, there is no better case study.

Summer camp for billionaires

Officially, there is no dress code at the conference beyond "relaxed" – or "humble," as a regular attendee once told me – though name tags (humble!) are encouraged, along with the gift gear passed out to all attendees: navy or cherry red fleeces, hoodies, vests, polo shirts and baseball caps, so marked by the neat "SV17" logo over the left breast. And while the "no press" policy means less imagery emerges from the event than from, say, red-carpet happenings, enough snaps of schmoozing lords of the universe exiting their cars on arrival or taking the air between meeting sessions get released to provide fairly good intel on how they define off-duty dress.

Which can best be characterised as "calculated schlubbiness." Or "Who can give the impression they care less about what they wear than the next guy?" Apparently, when you've reached the top of the mountain, literal and professional, it's really about the smarts, people, not the suits.

But it is the men, in their "what, this old thing?" rejection of the tailored sartorial culture in which most of them spend their days (the tech crowd excepted), whose attire is the most instructive. The predominant ethos being either the gym clothes shoved in the bottom drawer or back of the closet and then pulled out to meet with the personal trainer in the private gym look, or the "polo and baggy jeans on the back deck where no one can see you" style.

Going brand-free

Indeed, the only branded area on the body was really the foot, where Nikes were impossible to obscure, and the bridge of the nose, where the Persols, mirrored aviators and Oliver Peoples rest.

All of which made the few attendees wearing the traditional casual Friday uniform of jacket and shirt seem uptight and prissy (and even worse – old-fashioned) in comparison to their peers.

Even Jared Kushner, of navy-blazer-and-flak-jacket-combo-in-Iraq fame, seemed to have learned one thing from his experience and swapped the blazer for a beige crew neck and jeans. Still, he blended into the crowd better when simply wearing a dark long-sleeve athletic shirt, having traded buttoned-up for loosened-up (or at least as if he were about to head off for a chest-thumping hike up the mountainside).


The IT crowd

But that was nothing compared with the extreme relaxers, most notably the tech crowd, for whom dressing down is a natural form of camouflage – obvious thanks to the fact that their T-shirts and jeans actually fit them. (They are the Silicon equivalent of the tailored suit.) The best examples were perhaps Nick Woodman from GoPro in a faded black T-shirt with a playing-card bunny on the front, or Jeff Bezos in a black polo, sleeves straining around his biceps.

Indeed, aside from navy, there was, it's worth pointing out, a lot of black on display, including on Harvey Weinstein, Daniel Ek of Spotify and Barra – possibly as much as there is during fashion week. Which is interesting.

You can understand it. After all, this isn't really "off-duty" at all; it's faux off-duty. Family may come along for the fun, but attendees are still dressing for one another. To pretend otherwise is disingenuous. And that means that to a certain extent what they wear is being chosen to send a message, and define an attitude.

It's un-herd of

That being: Who can seem secure enough in their position to look fully unguarded? To not need any of the armor of power – aides or clothes or lawyers or polished shoes. To expose their soft underbelly (or loose underbelly as the case may be), the better to appear open and uncalculated with their peers.

Of course, if the rest of us adopted the same strategy, we might just look sloppy. A better takeaway is simple: Truth is, when it comes to casual clothing, we are all as subject to the effects of peer pressure and herd instinct as we are when it comes to professional clothing. It's just at the opposite extreme.

The NY Times

Would you take your boss seriously if he deliberately, and regularly, dressed down? Share your thoughts in the comments section below.