How to Dress Down Like a Power Player

(She was not the only attendee implicitly promoting her own brand-by-association, however. Ms. Trump wore a pair of Ivanka Trump Evia block-heel mules, currently available for purchase. Originally $99, they have been marked down twice on the Bloomingdale’s website to $55.44. Guess even though she is no longer officially associated with her brand, she still likes to shop there.)

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.

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).

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 Ms. Barra — possibly as much as there is during fashion week. Which is interesting.


There was a lot of black on display, including on Harvey Weinstein.

Drew Angerer/Getty Images

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.

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.

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