The business casual revolution of the 1990s and rise of tech billionaires in the early aughts supposedly ushered in a new era that freed employees from the shackles of dress codes. Mark Zuckerberg turned hoodies and jeans into a symbol of New Economy meritocracy, the uniform of whiz kid hackers shaking up the coat-and-tie aesthetic of traditional industries back east. In the digital economy, many imagined, the most successful companies would allow talented employees to wear whatever they wanted as they jumped around in colorful ball pits.

But as Facebook engineer Carlos Bueno wrote in his 2014 blogpost Inside the Mirrortocracy, we simply traded our hard-written dress codes for softly coded dress norms. The new world is actually not so free. The cognitive dissonance is plain to see on the faces of recruiters who pretend clothing is no big deal, but are clearly disappointed if you show up to a job interview in a dark worsted business suit. “You are expected to conform to the rules of The Culture before you are allowed to demonstrate your actual worth,” wrote Bueno. “What wearing a suit really indicates is – I am not making this up – non-conformity, one of the gravest of sins.”

As the rich got obscenely richer it seemed they were ever more determined to look as bland as possible.

This reality was quite evident earlier this month at the Sun Valley Conference, often branded as “summer camp for billionaires”. Since the tradition’s founding in 1984, organizers have pulled together some of the wealthiest, most influential people for a multi-day conference. A treasure chest of A-list CEOs, tech entrepreneurs, billionaire financiers, media moguls and others turn up for the invite-only meeting to privately decide the future of our world.

This year’s attendees included Jeff Bezos, who continued his remarkable transformation from geek to beefcake. Looking like a successful Soul Cycle instructor, he sauntered around the resort grounds in pearl gray jeans, a tight black T-shirt, and a stacked assortment of colorful bracelets (seemingly from the American luxury company David Yurman).

David Zaslav, CEO of Warner Brothers, at least made a respectable attempt at pulling a look together by wearing a tan corduroy trucker jacket with slim-straight blue jeans, tasteful white sneakers, and a white bandana jauntily tied around his neck. But most male attendees arrived in limp polos, T-shirts, and simple button-ups. Sam Altman, billionaire CEO of OpenAI, wore a plain gray T-shirt with blue jeans, a black backpack slung across both of his shoulders, looking like he’d arrived for freshman orientation.

It’s not that the outfits are necessarily bad, although many of them are, but one wonders if we may have lost something in the transition away from the coat-and-tie. A few generations ago, men in this social class would have worn something visually more interesting. In the 1930s, Apparel Arts – a premier menswear trade publication that advised men on how to dress for various environments – recommended the following for resort wear: navy double-breasted sport coats with spotted mufflers and high-waisted trousers while at Cannes, mocha-colored linen beach shirts and wide-cut slacks secured with self-straps when vacationing in the French Riviera, and white shawl collar dinner jackets paired with midnight blue, tropical worsted trousers and white silk dinner shirts for semi-formal evening wear.

The advantage of these clothes has nothing to do with respectability or class, but rather their ability to confer a distinctive silhouette. The tailored jacket is especially useful in this regard. Built from many layers of haircloth, canvas and padding, which are sewn together with pad stitching and then shaped through the use of darts and skilled pressing, a tailored jacket confers a flattering V-shaped silhouette even when there isn’t one. The presence of a silhouette is why Stacey Bendet, founder of fashion company Alice & Olivia, is consistently the most stylish person at these conferences (this year, she wore flared pants, long leather coats, giant sunglasses, and Westernwear hats, each element working to create a distinctive shape). By contrast, Tim Cook’s basic polo and slim jeans did little besides recreate his corporal form.

In his book Distinction, Pierre Bourdieu correctly recognized that the notion of Good Taste is nothing more than the habits and preferences of the ruling class. Of course, he was not the first to make this observation. At the turn of the 20th century, German sociologist Georg Simmel noted that people often use fashion as a form of class differentiation. According to Simmel, styles spread downward as the working-class imitates its perceived social superiors, at which point, members of the ruling class move on. However, the publication of Distinction in 1979, based on Bourdieu’s empirical research from 1963 to 1968, sets it apart, particularly in our understanding of men’s style. These were the waning years of the coat-and-tie. By the time the book was translated into English in 1984, the suit was pulling its last dying gasp before men’s dress would be permanently changed by the rise of Casual Fridays, tech entrepreneurs and remote work.

The ruling class today is hardly inspiring in terms of taste. The preponderance of tech vests, which have replaced navy blazers, demonstrates that socio-economic class still drives dress practices, albeit with less appealing forms. The irony is that, while elites dress increasingly like the middle class preparing for a Whole Foods run, wealth inequality in the United States has mostly worsened every decade since the 1980s, the last era when men were still expected to wear tailored jackets.

If there’s any shining light in all this, it’s that the history of 20th century dress is about how influences have switched. As the century progressed, men started to take dress direction from a variety of social classes – artists, musicians and laborers – and not just those with financial or political power. Many of the more inspiring fashion moments during this period were about how rebellious youths struck a rebel pose against The Establishment – swing kids and hep cats; bikers, rockers and outlaws; beats and beatniks; modernists and mods; drag and dandies; and hippies and bohemians among them. In the last few years, Zuckerberg and Bezos have made some effort to break out of the fleece conformity, and the Nvidia CEO Jensen Huang does look pretty stylish in his head-to-toe black uniforms involving various leather jackets. But for the most part, it’s better to look elsewhere nowadays for dress direction. The ruling elite may shape our world, but don’t let them shape your wardrobe.

• Derek Guy is a menswear writer who runs men’s style site Die, Workwear!