The ultimate trading-floor flex? A Snoopy Swatch. Or a Casio calculator. Why lots of money men (still) favour novelty watches.
3 min
How do you tell the time? Neal W. McDonough, the COO of a finance and policy startup in Ho-Ho-Kus, N.J., looks to Charlie Brown, the loveable, miserable “Peanuts” protagonist. An illustration of the character occupies the exec’s watch dial, Brown’s stout arms acting as the minute and hour hands.
McDonough, 55, bought the kooky Timex for a Valentine’s Day trip about five years ago, along with a matching model depicting Lucy van Pelt (Brown’s frenemy) for his then-girlfriend. To his surprise, he kept wearing the $150-ish ticker after the trip. “It’s now my business watch,” he said, adding that such a non luxury model can telegraph that he’s under no obligation to be flashy. “I have nothing to prove to anyone,” he said. “And the fun thing is, a lot of people notice [my watch].”
Though finance guys famously flaunt Rolexes or Patek Philippes on their wrists, an established subspecies of money men goes the other way entirely. In place of a sleek steel case and elegant ceramic dial? Mickey Mouse. SpongeBob SquarePants. Fanta-orange rubber straps.
Over the years, highfliers have made headlines for sporting Swatches. (See: Blackstone Group CEO Stephen A. Schwarzman or former Goldman Sachs CEO Lloyd Blankfein .) That “wealthy guy, cheap watch” ethos continues to resonate in boardrooms and on trading floors, with men of all seniority levels embracing plasticky, offbeat designs, from superhero models to calculator Casios. Many resemble something you might win in a claw machine. Priced from $30 to a few hundred bucks, they’re a bit of fun and a different sort of flex, conveying an “I don’t need a Rolex” bravado that comes from having made it. Call them anti-status watches.
Patrick Lyons, the managing partner of a family office in New York, rotates two contrasting watches: a 1988 Santos de Cartier and a Nickelodeon “SpongeBob SquarePants” model with a tangerine strap.
The Cartier, a family heirloom, is a slice of French sophistication; the Nickelodeon dial features a giant image of a pink starfish named Patrick Star who lives under a rock. Lyons, 35, likes that the second watch is idiosyncratic—and that its starfish shares his name. “I wear that more often than my Cartier,” he said, adding that he hopes to pass down both models to future offspring.
Leroy Dikito, 42, an executive director at JPMorgan Chase in New York, chose his $450 “Avengers” watch from Citizen because it reminds him of his father, who loved comic books. Though its stainless-steel strap reads urbane enough, its cheerfully garish dial slices together images of the Hulk, Iron Man, Captain America and other superheroes. Working in finance, you need to be “serious all the time,” so a fun watch brings welcome levity, said Dikito. “People need to know there is more than the big job and the title.”
Since a suit can only inject so much colour, a watch offers that rare opportunity to “show off your personality,” said Eli Tenenbaum, 36, the director of corporate development for a New York private-equity firm. Plus, he noted, “If you wear a fancy watch, chances are someone else may be wearing the same one.” Tenenbaum runs little risk of twinning with a colleague when he straps on his Mickey Mouse or Snoopy Swatches, worn with premium Brioni or Zegna suits.
Evan Vladem, 37, considers his Casio calculator watch a neat “ice breaker” when schmoozing, a professional obligation for the partner at a financial advisory in Fort Lauderdale, Fla. “It came in handy to break up awkward moments,” he said of the black, $30-ish design, a Casio classic. At a dinner with an insurance partner a few years ago, he recalls, the conversation petered out after an exchange about a client’s situation, which involved some financial arithmetic. “I pulled out my wrist and said, with a smile, ‘Well, I’m happy I have my trusty calculator watch to help me here,’” said Vladem. “We both laughed. [It] kicked off another conversation.”
Even men who have invested heavily in high-end horology seem to be falling for cheap, kitschy designs. Scott Jay Kaplan, 44, a film producer and financier for Brooklyn company CoverStory, owns pricey models from Rolex and Audemars Piguet. But for daily wear he’s currently favouring a super-chunky $25 watch he bought in Argentina this past winter, a model similar to a G-Shock but by an unfamiliar brand. He says he has received a lot of compliments on it, and it has held up surprisingly well. “I bought it because it looked silly,” he said. “Not for clout.”
McDonough, the Charlie Brown fan, urges anyone considering a novelty ticker to follow just one rule: Don’t splurge. “I think the whole idea of luxury watch brands coming out with ‘kitsch’ watches is…a little bit absurd,” he said. “So anything over, say, $500 would be out.”
Prop styling by Marina Bevilacqua
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Rugged coastal drives and fireside drams define a slow, indulgent journey through Scotland’s far north.
A haven for hedge-fund titans and Hollywood grandees, Greenwich is one of the world’s most expensive residential enclaves, where eye-watering prices meet unapologetic grandeur.
Their careers spanned the personal computing, internet and smartphone waves. But some older workers see AI’s arrival as the cue to exit.
4 min
Luke Michel has already lived through two technology overhauls in his career, first desktop publishing in the 1980s and online publishing later on. But AI? He’s had enough.
So when his employer, the Dana-Farber Cancer Institute, made an early-retirement offer to some staff last year, the 68-year-old content strategist decided to speed up his exit. Before, he had expected to work a couple more years.
“The time and energy you have to devote to learning a whole new vocabulary and a whole new skill set, it wasn’t worth it,” he said.
It isn’t that he’s shunning artificial intelligence—he is learning Spanish with the help of Anthropic’s Claude. But, at this point, he’s less than eager to endure all the ways the technology promises to upend work.
“I just want to use it for my own purposes and not someone else’s,” he said.
After rising for decades and then hovering around 40% in the 2010s, the share of Americans over 55 years old in the workforce has slipped to 37.2%, the lowest level in more than 20 years.
The financial cushion of rising home equity and stock-market returns is driving some of the decline, economists and retirement advisers say.
But for some older professionals, money is only part of the equation.
They say they don’t want to spend the last years of their career going through the tumult of AI adoption, which has brought new tools, new expectations and a lot of uncertainty.
Many people retire when key elements of their work lives are disrupted at once, said Robert Laura , co-founder of the Retirement Coaches Association and an expert on the psychology of retirement.
“Maybe their autonomy is being challenged or changed, their friends are leaving the workplace, or they disagree with the company’s direction,” he said.
“When two or three of these things show up, that’s when people start to opt out.”
“AI is a big one,” he adds. “It disrupts their autonomy, their professionalism.”
Michel, whose work required overseeing and strategizing on website content, has been here before.
When desktop publishing arrived in the 1980s, he was a graphic designer using triangles and rubber cement.
The internet’s arrival changed everything again. Both developments required new skills, and he was energized by the challenge of learning alongside colleagues and peers.
It felt different this time around. “Your battery doesn’t hold a charge as long as it used to,” he said.
He would rather spend his energy volunteering, making art, going to operas and chairing the Council on Aging in North Andover, Mass., where he lives.
In an AARP survey last summer of 5,000 people 50 and over, 25% of those who planned to retire sooner than expected counted work stress and burnout as factors.
About half of those retired said they had left work at least partly because they had the financial security to do so.
In general, older Americans are less likely than younger counterparts to use AI, research shows.
About 30% of people from ages 30 to 49 said they used ChatGPT on the job, nearly double the share of those 50 and older, according to a 2025 Pew Research Center survey of more than 5,000 adults.
Baby boomers and members of Generation X also experienced the sharpest declines in confidence using AI technology, according to a ManpowerGroup survey of more than 13,900 workers in 19 countries.
“We as employers aren’t doing a good enough job saying (to older workers), we value the skills that you already have, so much so that we want to invest in you to help you do your job better,” says Becky Frankiewicz , ManpowerGroup’s chief strategy officer.
Jennifer Kerns’s misgivings about AI contributed to her departure last month from GitHub, where the 60-year-old worked as a program manager.
Coming from a family of artists, she said, it offends her that AI models train on the creative work of people who aren’t compensated for their intellectual property. And she worries about AI’s effect on people’s critical-thinking skills.
So she was dismayed when GitHub, a Microsoft-owned hosting service for software projects, began investing heavily in AI products and expecting employees to incorporate AI into much of their work. In employee-engagement surveys, the company had begun asking them to rate their AI usage on a scale of 1 to 5.
When it came time to write reports and reviews, colleagues would suggest that she use ChatGPT.
“I’d be like, ‘I have no idea how to use that and I have no interest in using AI to write anything for me,’” she said.
It would have been more prudent to work until she was closer to Medicare eligibility, she said. But by waiting until her children were out of college and some of her stock grants had vested, the math worked.
Her first act as a nonworking person: a solo trip to Scotland, where she took a darning workshop and learned how to repair sweaters.
“The opposite of AI,” she said.
Employers already under pressure to cut workers—such as in the tech industry—may welcome some of these retirements, said Gad Levanon , chief economist at Burning Glass Institute, which studies labor-market data.
“The more people retire, the fewer they have to let go,” he said.
Some of the savviest tech users are also balking at sticking around for the AI upheaval. Terry Grimm, who worked in IT for 40 years, retired from his senior software consultant role at 65 last May.
His firm had just been acquired by a bigger firm, which meant learning and integrating the parent company’s AI and other tech tools into his work.
Until then, Grimm expected he might work a couple more years, though he felt that he probably had enough saved to retire.
“I just got to the point where I was spending 40 hours at work and then 20 hours training and studying,” said Grimm, who has since moved with his wife from the Dallas area to a housing development on a golf course in El Dorado, Ark.
“I’m like, ‘I’ll let the younger guys do this.’”
