What does a “rich girl” look like now?

I’m chatting with that hot guy from Industry after the Boss fashion show in Milan. He smiles warmly and broadly until I bring up finance, which is technically the theme of his TV show. (Viewers know the real theme of Industry is sensual wellness tools, followed closely by Toteme blazers. Still, the world of finance is a close third.) “Industry has made me so scared of really rich people,” says the actor bluntly. “Our show makes it so clear that they’re everywhere—these secretly wealthy, super powerful people who just show up in big gray sweaters and leggings at the cafe and then open up their laptop and ruin everyone’s lives. Like, you’d never know.”

He’s talking about the “quiet luxury” school of billionaires—the one highlighted by both Industry and its more highbrow cousin Succession—where wealthy psychopaths wear $8,900 cardigans from Brunello Cuccinelli and $2,850 silk tops from Loro Piana. And, sure, logo-free beige cashmere certainly has a chokehold on #RichTok videos about how "real" billionaire families get dressed. But even the actual moguls who attended Milan Fashion Week this season—most famously Mark Zuckerberg at Prada—went above and beyond the anonymous outfits that look like they're from Uniqlo but cost more than a car.

These moguls looked polished but also interesting— even Mr. Zuckerberg, in a nicely fitting camel polo with deep-brown slacks, hair just a little bit messy—as if blending in was suddenly a portfolio liability. Meanwhile, the runways created a debate with shirts and shoes: Should crazy-expensive clothes look lavish, or is the ultimate flex wearing something perfect until it falls apart... then wearing it some more, because you’re too powerful for anyone to object? As crystal-crammed party dresses and slouchy pre-stained pants staked their claim on Milan, they asked a question: What does a rich girl look like in 2026?

The Prada scarf with another rich-kid riff: a dress that’s also a half-zip

The easy answer is—sorry—Carolyn Bessette Kennedy. The style icon would be 60 today, but because of her chilling and tragic death, she’s frozen in time at 33. Now her image echoes on Pinterest mood boards, and her living avatar, the excellent actress Sarah Pidgeon, flits across our TV screens thanks to Love Story, the kind of true, absolutely addictive TV show about her life.

Love Story has sparked a new frenzy for muted urban elegance, mixed with just a touch of Gen X irony. (Bessette Kennedy famously worked at Calvin Klein in its 1990s heyday, adding to the allure.) Milan wasn’t immune to her charms: MM6 Maison Margiela, Jil Sander, Tod’s, and even the soccer brand Fila made riffs on Bessette Kennedy’s well-documented camel-colored pencil skirt, paired with brown boots and a black sweater. Karlie Kloss, a billionaire by marriage and independent investor, wore Gucci’s version, which swapped the hushed beige wool for printed logo canvas.

Model Abby Champion—who is married to Kennedy scion Patrick Schwarzenegger—between fashion shows

CBK’s signature messy ponytail appeared at Prada, Giorgio Armani, and Fendi. Diesel did a take on her thick-framed, oval-shaped sunglasses from Selima Optique. And patrician blondes with wide-set stares took over the catwalks, including Liisa Winkler, Bodine Van Galen, and Abby Champion, who is married to actor Patrick Schwarzenegger, the grandnephew of JFK.

There’s another school of rich-girl style that says if you’re a secret scion, you might as well use your time and focus to make and mend your own clothes—or even make your own kiln pottery at Bard College. When French model Ambre Roumeau walked Bottega Veneta carrying a see-through bag with a knitting project inside, it made the point that Bottega girls have Real Designer Money, but they’re still trying to crochet their own stuff. This also happened at Prada, where Bella Hadid and Liu Wen wore hand-knit striped scarves on the catwalk. An Italian fashion editor wore her own to the brand’s re-see appointments the next day in a kind of homage. “I made it myself,” she told me. “It costs maybe four euros for the yarn. Only today, everyone at my office asked if it was Prada. Can you believe?”

Prada also kept its runway shirts wrinkled and its pink kitten heels lightly stained and scuffed at the toe, adding to the lived-in aesthetic prized by those who believe looking experienced, not perfect, is the real secret handshake for the rich. Maybe that’s why Marni had its own DIY project: The brand took the $19.99 plastic necklaces from its 2012 H&M collab and recast them in silver metal alloys that will eventually sell for thousands.

Emily Ratajkowski on the Gucci runway

But perhaps the most fun way to look expensive is to look fantastically cheap. It happened at Gucci, where Emily Ratajkowski sported a teeny, clingy party dress covered in tiny crystals. Creative director Demna instructed her to flip her hair and adjust her straps as she walked down the catwalk, doing a perfect imitation of Mikey Madison in Anora—the heart-stab of a movie about a stripper who briefly gets close to an oligarch’s son. Blumarine went with a similar Girls! Girls! Girls! vibe, going with full black lace dresses and piles of fake pearls and gold chains. Backstage, designer David Koma put on a giant pair of sunglasses whenever the cameras came through, playing the part of a high-rolling mogul when in fact he’s a thoughtful and considered fashion expert. Roberto Cavalli designer Fausto Puglisi bet big on sheer black lace dresses, big-shouldered blazers, and giant ’80s earrings that recalled Sigourney Weaver’s rich-bitch template in Working Girl. By the time Philipp Plein sent his models down the catwalk clutching stacks of (fake) cash, it didn’t even look like a publicity stunt—more like a shortcut that admits money is the actual status accessory on our outfits, not the handbags we buy with it.

Why do we all want to seem wealthy, even if we can’t agree on what a rich girl actually looks like? The hard answer is that so often, money is the closest thing we have to protection. We can use it overtly for better medicine, cleaner water, fresher food, and warmer homes. (Not to mention better seats at Oh, Mary! and better shoes at Bergdorf Goodman.) We can use it covertly for things like hotter life partners, less work pressure, and the ability to drop everything and chase a creative passion—like, say, knitting stripy scarves.

Looking like a member of a club is often synonymous with becoming that member, and the advantages of being rich are too major to ignore. If looking the part helps us get our secondhand Miu Mius through the door, why wouldn’t we try? Yes, some designers lionize the bourgeois babes; witness the cutie-pie-blazers-and-jeans combos at Blaze Milano or the rumpled gray student suits at Emporio Armani. Some brands just want to make great clothes for great women going to work. But as one of those women myself, even I can admit that sometimes, I’d like to just be a Radziwill instead of a cool boss wearing next season’s Boss.

A Marni by H&M by Marni necklace on the catwalk

On the last day of Milan Fashion Week, rumors cartwheeled across the Duomo plaza: Mark Zuckerberg and his wife, Dr. Priscilla Chan, were strolling past the Duomo. In the Instagram footage released the next day, the couple looks happy and a little bit exhausted—and they’re wearing flannels and sweatsuits like they just stepped out of a college dorm. It’s a good reminder that being rich and looking rich are two entirely different things. But, gosh, it sure is fun to wear that camel cashmere pencil skirt.