Why is Gen Z obsessed with the "Old Money" style?

A quarter century after their untimely deaths, JFK Jr. and Carolyn Bessette continue to be flawless style icons for a whole new generation. ©RON GALELLA//GETTY IMAGES

Zach Weiss, a writer and practitioner of the old money aesthetic, finds it interesting to see younger generations idolizing these styles. "At some point, you think you've discovered it, which I'm sure I did at that age," he says. Weiss was influenced by this look in high school when he started playing tennis and sought alternatives to the shabby t-shirts and flashy Nike outfits worn on the courts. After some research, he discovered tennis teams, Lacoste polos, and similar attire, which helped him develop his personal style.

Today, Weiss often dresses like a stylish Great Gatsby character, an anachronism so evident that when he wore a white blazer, banker-striped shirt, and yellow tie to the US Open last year.

Now 31, Weiss finds it fascinating to see the style he discovered in his youth now being embraced by a new generation, tied with a bow and served as social media content.

Stanford law professor Richard Thompson Ford, author of Dress Codes: How the Laws of Fashion Made History, describes the old money aesthetic as evocative of mid-20th century East Coast elites—think of clothes worn at prep schools or Ivy League colleges. These are classic, non-trendy, and durable items. Literally timeless, they could be worn today or 100 years ago without looking out of place. This style, which might have simply been called "preppy" 10 or 20 years ago, now holds a different meaning for Gen Z.

Matt Damon and Jude Law starred in the 1999 film The Talented Mr. Ripley. / ©Miramax/Everett Collection.

Anyway, the nuances of this style often get lost amidst the younger generations' quest to turn everything into short reels and striking videos. Ford says, "There was also an incomprehensible aspect to it. You'd try to buy something from a store that no one wore, only found in New Haven, Connecticut, or Martha's Vineyard. Some clothes were worn, thoroughly worn out; it was part of the aesthetic. Looking worn was part of the charm. And some things were just ugly! Colors like bright pink, lemon green, Nantucket red pants. I don't think the current TikTok generation sees these as 'old money,' but they are clear markers of belonging to a certain environment."

Weiss, adding, "There's a science to this," refers to The Official Preppy Handbook as a milestone, an enlightening guide. "Obviously, there are versions that are not very chic. Like the chunky knit sweater you throw over your shoulder."

The rise of online hunger for the old money lifestyle dreams of the zeitgeist certainly helps. When you mention Saltburn, the new Netflix series Ripley comes to mind, which has settled into cultural consciousness with its 1999 adaptation of Patricia Highsmith's The Talented Mr. Ripley novels, starring Jude Law, Matt Damon, and Gwyneth Paltrow. While Ryan Murphy's latest film, Feud: Capote Vs. the Swans, pays homage to the high style of mid-20th-century social elite in New York, popular brands like Aimé Leon Dore and Drake's often mimic and remix these stylistic gestures for their own use – quite successfully.

Prince Mateen poses next to a classic Ferrari convertible. (Image credit: Mateen/@tmski/Instagram)

The real question is: Why now? Ford says, "The first thing that comes to mind is nostalgia. Nostalgia for better times or for when the United States and the West seemed more confident." Indeed, in these clothes, there seems to be a longing for a type of normalcy with a foundation in tradition and classicism that cannot be found in today's endless chaos.

Avery Trufelman, host of the popular fashion podcast "Articles of Interest" - who spent an entire season delving into the afterlife of thorough research - has a theory. "In some ways, I think it's a reaction to trends," she tells me. "It reminds me of the Ivy style in the 1960s, which was supposed to be dead but then revived because there were so many trends at that time, and people thought, 'I'm going back to what I know, what's chic and safe.' This also reminds me of the trend explosion we've seen after the pandemic." Indeed, whenever a new trend emerges, isn't it comforting to think about wearing a navy blazer jacket?

Ralph Lauren Purple Label 2022 collection ©Ralph Lauren.

Weiss also thinks this is a reaction post-pandemic, but it's also linked to a desire to dress up again after years of wearing sweatpants and athleisure. "Post-Covid, there was something about dressing by choice," she says. "In a world where we used to dress for work, now there's the idea of dressing by your own volition."

Personally, amidst unprecedented wealth inequality where young people are told they may never own a home and the American dream promised to them might be dead, I find it fascinating that they dress essentially like the people who ruined everything for them. I've noticed my TikTok feed overflowing with slideshows of old money aesthetics set to Rolls-Royces, with intense speeches about late-stage capitalism – a surprising contrasting of ideas.

Ford, mentioning the long history of ironic, somewhat mocking use of the status symbols, refers to the time when Black and Latin people wore exaggerated suits against traditional men's tailoring. "I could say it's half-ironic how people embrace these things [but] there's definitely a lot of genuine affection towards appearances."

Ripley TV Series on Netflix. (Image credit: @Netflix)

Trufelman also notes that people don't dress like enemies. "I think there's a comfort in dressing old money," she says. "I don't want to be snotty, but these guys who are ruining the world in their black t-shirts like Elon Musk aren't new money." Indeed, old money is far enough removed to sand down most of the rough parts in the rearview mirror. What we're left with are great clothes but not much substance. As Trufelman puts it, "It's almost like a costume for social media."

However, Weiss, who has long embraced this aesthetic as the default dress code, has some thoughts on why it's become so popular. "Basically, it looks nice," she says. Indeed, despite its classic nature, the old money aesthetic harbors a surprising amount of diversity within it. Weiss adds, "For instance, I'm a cheerful preppy," she adds, "which is somewhat anti-WASP, so I shake it up a bit." If everyone from Tyler, the Creator to J.Crew, Emerald Fennell to Nigo can reference it, who can't find their own angle on this trend?

"Pleasant and comfortable," says Weiss. "It's nice to go to the Ralph Lauren Mansion on Madison Ave and play that role. I forget who it was, but someone in the Very Ralph documentary said, 'You live in this very utopian world among movie characters. It's a safe place to be.'"

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