‘What Was I Thinking?’ The Big-Ticket Items People Regret

While it may be true that money can’t buy happiness, that doesn’t stop people from trying.

And then wishing they hadn’t.

Many of us have had a big-ticket expenditure that we later come to regret. Maybe it’s something meant to convey status, which we realise later did nothing of the sort. Maybe it was to fulfil dreams of a luxury lifestyle, only to discover that we’ve bought a bottomless money pit.

We asked Wall Street Journal readers to share their stories of pricey purchases that ultimately led to disappointment. Below are some of their stories and reflections—with some free advice to their younger selves.

The wristwatch of his dreams

“It was back in day of wingtip shoes, white shirts and red ties,” says Bryan Desloge, who began his career at IBM in 1984. And like many rookie employees, Desloge wanted to fit in. “I bought suits. I took my earring out. I cut my hair and I registered in the Republican Party,” he says. To complete the look, he paid over $7,000 for the wristwatch of his dreams—a Rolex Submariner. It was a hefty sum, considering he was making roughly $18,000 a year.

Now 64 and retired, Desloge says his younger self saw the stainless-steel watch as a status symbol. “The older guys had nice dress watches already, while I wore a Casio or a Timex.” Just two years after buying the Rolex, however, Desloge realised the timepiece was impractical for him. “The Rolex is great, but I don’t want to look at a clock face,” he says, “and the glow-in-the-dark hands are hard to read at night.”

Desloge, who lives in Tallahassee, Fla., recently tried to give the Rolex to his son, who turned him down. So it remains tucked away in favor of a Garmin smartwatch, which has a fitness tracker, alerts and email, among other features. Purchased for about $500, the Garmin can multitask in ways his Rolex cannot. “I will probably wear that watch for the rest of my life,” Desloge says.

Cabin fever

The family called it “the little brown house,” says Michael Kotas of his vacation cabin in the mountains overlooking Tucson, Ariz. In 2005, Kotas and his wife paid $120,000 for the 1950s cabin, and it needed a lot of work.

“We bought it from an older couple, who had dark rugs and wood paneling,” says Kotas, who is now in his mid-60s and retired from a job in technology sales. He redid the cabin “with a cool Manhattan vibe,” updated the electrical wiring and corrected a flooding issue in the basement. In all, Kotas estimates he spent $60,000 in upgrades.

But his financial headaches were far from over.

Even though Kotas owned the cabin, the federal government owned the land it sat on, since it was located within the Coronado National Forest. Leasing the land cost $800 a year when the cabin was purchased, but eventually grew to $3,600 a year by the time it sold.

During that time, two fires came within 100 yards of the cabin, jacking up Kotas’s fire-insurance premiums. Then, a species of bark beetle attacked ponderosa pines there, and the Forest Service required cabin owners to remove infested trees around their property, costing $1,000 to $1,200 a pop. “I counted all my trees around my house and thought, ‘I can’t afford this.’ ”

Over time, Kotas’s children didn’t want to go to the cabin anymore, saying “there was nothing to do,” he says. “We ended up spending about five nights a year there for the last several years.” Kotas, whose year-round home also is in Tucson, came to the realisation that he wasn’t getting his money’s worth. “It became an albatross,” he says.

The tipping point came when a man parked his truck just 100 feet from the cabin and lived out of his vehicle on the side of the road. Kotas sold the cabin in 2022 for $195,000.

“I would probably never buy a vacation home again,” he says. “It was a tough lesson to learn. I wish the [new] buyers well, but all I can say is, ‘Good riddance!’ ”

RV to nowhere

After retiring from a career in ophthalmology, Gordon Preecs bought a large pickup truck in 2013 and a 22-foot travel trailer in 2017 with the dream that he and his wife, Connie Preecs, would visit national parks around the country. Combined, the new vehicles cost around $50,000.

Living in Seattle at the time, the couple started out by taking the RV on short trips, such as an event for woodcarvers in Washington state. It didn’t take long for them to feel pinched in a 120-square-foot RV. “I thought we’d have our own hotel” with an RV, says Preecs, who is now 75 and living in Round Rock, Texas. “But we had to just shove things in there. The kitchen counter was hand’s breadth wide, and the bathroom was like a phone-booth shower. If I dropped the soap, I couldn’t pick it up.”

Three years after purchasing the trailer, Preecs and his wife relocated to Texas to be closer to their grandchildren. Still, they were able to visit Grand Teton and Yellowstone national parks in the Northwest. That’s when they felt the financial pinch of RV ownership.

“At 6 miles per gallon and $60 to $80 a night at RV parks, the expenses really added up,” he says. “We found it was an inefficient way to travel.” Some of the RV parks are located in funky, backwater places, he says. And setup and breakdown at every stop became a hassle. “You want to be free, but you’re not.”

In 2020, they sold the trailer, which had less than 5,000 miles of use, and the pickup for a combined $32,000. With the proceeds, Preecs bought a Tesla.

Outfitted and outwitted

As a vintner in California, much of Pam Starr’s work takes place outside among the grape vines. “I live in jeans and winemaker vests, T-shirts and sometimes boots,” says the 63-year-old. “So I can tear my clothes on a vine or get barrel slime on me” and it doesn’t really matter.

A few years ago, a well-heeled friend with an eye for fashion convinced Starr, who lives in Napa, to join her in San Francisco for a meeting with her couturier—a person who creates luxury clothing to the client’s specifications. The friend had told Starr that she wouldn’t have to buy anything, but this particular couturier was very persuasive, Starr recalls.

For example, the couturier held up a gauzy swimsuit coverup with white sequins and said, “You have to wear this swimsuit coverup by the pool.” Starr paid $1,800 for a custom coverup, but later it hit her: “I don’t wear a coverup when I’m at the pool because I’m actually in the pool.” To this day, it has never been worn. Starr says she spent another $1,800 for an off-the-shoulder silk shirt with three-quarter length sleeves.

The quality of the clothing was low, Starr says. “That silk shirt turned out to be my most disappointing piece,” she says. It didn’t clean well, and hasn’t retained its shape. Many of the pieces she purchased haven’t held up well, she says, even though she rarely wears them. “Out of the 15 items I had made for me, I loved maybe three,” Starr says. “That’s more than $20,000 worth of clothes, and I should have gotten more out of them.”

If she could go back in time, Starr says, she would say to herself, “ ‘Listen, Pam. Pick two things and start slowly. If you like them, you can expand into other things.’ ” Also, she would pause to ask herself how often she would actually wear the clothing.

“Because of a friend, I ended up in a couture shop,” Starr says. “In that world, it’s uncharted territory for me. The couturier pulls you in really hard.” Knowing what she knows now, Starr says, “if I needed someone to design a gown for me, I wouldn’t go back there. I would go to a seamstress locally.”

LIKE MARVEL VILLAINS, most fashion writers have origin stories. Mine began with a navy nylon Prada purse, salvaged from a Boston thrift store when I was a teen in the 1990s. Scuffed with black streaks and sagging, it was terribly beat-up. But I saw it as a golden ticket to a future, chicer self. No longer a screechy suburban theatre kid, I would revamp myself as sophisticated, arch, even aloof. The bag, I reasoned, would lead the way.

That fall, I slung it against my shoulder like a shotgun and marched into school, where a girl far more interesting than I was called out, “Hey, cool bag.” After feigning apathy —“I don’t know, you could use a Sharpie on a lunch bag and it would look the same”—we became friends. She introduced me to a former classmate who worked at a magazine. That woman helped me get an internship, which led to a job.

Twenty years later, I still wonder how big of a role that Prada purse played in my future—and whether designer bags can function as a silent partner in our success. Branded luxury bags took off in 1957, when Grace Kelly posed with an Hermès bag in Life magazine. (Hermès renamed that bag “the Kelly” in 1973.) The term “status bag” was popularised in 1990 by Gaile Robinson in the Los Angeles Times, describing any purse that projects social or economic power. Not surprisingly, these accessories are costly. Kelly bags cost over $10,000; ditto Chanel’s 11.22 handbag. Some bags by Louis Vuitton and Dior command similar price points. The cost isn’t repelling customers—both brands reported revenue surges in 2023. But isn’t there something dusty about the idea that a branded bag carries meaning along with your phone and wallet? How much status can a status bag deliver in 2024?

Quite a lot, said Daniel Langer, a business professor at Pepperdine University and the CEO of Équité, a Swiss luxury consulting firm. Beginning in 2007, Langer showed a series of photo portraits to hundreds of people across Europe, Asia and the U.S., then asked them 60 questions. Those pictured carrying a luxury handbag were seen as “more attractive, more intelligent, more interesting,” he said. The conclusion was “so ridiculous” to Langer that he repeated the studies several times over the next decade and a half. The results were always the same: “Purchasing a ‘status bag’ will prepare you to be more successful in your social actions. That is the data.”

Intrigued, I gathered various Very Important Purses—I borrowed some from friends, and others from brands—to see if they could elevate my station with the same unspoken oomph as a “Pride and Prejudice” suitor.

First, I took Alaïa’s Le Teckel bag—a narrow purse resembling an elegant flute case and carried by actress Margot Robbie—to New York’s Carlyle Hotel on a Saturday night. The line for the famous Bemelmans Bar stretched to the fire exit. “Can I get a table right away?” I asked the host, holding out my bag like a passport before an international flight. “It’s very busy,” he said in hushed tones. “But come sit. A table should open soon.” I sank into one of the Carlyle’s lush red sofas and sipped a martini while waiting—a much nicer way to kill 30 minutes than slumped against a lobby wall.

Wondering if this was a one-time thing, I called up Desta, the mononymous “culture director” (read: gatekeeper) who has worked for Manhattan celebrity hide-outs like Chapel Bar and Boom, the Standard Hotel bar that hosts the Met Gala’s official after party. “Sure, we pay attention to bags,” he said. “Not too long ago at Veronika,” the Park Avenue restaurant where Desta also steered the social ship, “we had one table left. A woman had a Saint Laurent bag from the Hedi Era,” he said, referencing Hedi Slimane , the brand’s revered designer from 2012 to 2016. “I said, ‘Give her the table. She appreciates style. She’ll appreciate this place.’”

Some say a status bag can open professional doors, too. Cleo Capital founder Sarah Kunst, who lives between San Francisco and London, notes that in private-equity circles, these accessories can act as a quick head-nod in introductory situations. Kunst says that especially as a Black woman, she found a designer bag to be “almost like armour” at the beginning of her career. “You put it on, and if you’re walking into a work event or a happy hour where you need to network, it can help you fit in immediately.” She cites Chanel flap bags made from the brand’s signature quilted leather and stamped with a double-C logo as an industry favourite. “People love to talk about them. They’ll say, ‘Ohhh, I love your bag,’ in a low voice.” They talk to you, said Kunst, “like you’re a tiger.”

For high-stakes jobs that rely on commissions—sports agents or sales reps, for instance—a fancy handbag can help establish credibility. “It says, ‘I’m succeeding at my job,’” said Mary Bonnet, vice president of the Oppenheim Group, the California real-estate firm at the centre of Netflix reality show “Selling Sunset.” As a new real-estate agent in her 20s, Bonnet brought a fake designer bag to a meeting. To her horror, a potential buyer had the real thing. “I work in an industry where trust is important, and there I was being inauthentic. That was a real lesson.” Now Bonnet rotates several (real) Saint Laurent and Chanel bags, but notes that a super-expensive purse could alienate some clients. “I don’t think I’d walk into [some client homes] with a giant Hermès bag.”

Hermès bags are supposedly the apex predator of purses. But I didn’t feel invincible when I strapped a Kelly bag around my chest like a pebbled-leather ammo belt. The dun-brown purse cost $11,800, a sum that prompted my boyfriend to ask if I needed a bodyguard. Shaking with “is this insured?” anxiety, I walked into a showing for an $8.5 million apartment steps from Central Park. I made it through the door but was soon stopped by a gruff real-estate agent asking if I had an appointment. No, but I had an Hermès bag? Alas, it wasn’t enough. The gleaming black door closed in my face.

“What went wrong?” I asked Dafna Goor, a London Business School professor who studies the psychology behind luxury purchases. “You felt nervous,” she replied. “That always makes others uncomfortable, especially in a high stakes situation,” like an open house with jittery agents. Goor said recognisable bags from Louis Vuitton and Christian Dior are also often faked, which can lead to suspicion if not paired with “other signals of wealth.”

“You can’t just treat a bag as a backstage pass,” said Jess Graves, who runs the shopping Substack the Love List. Graves says bags are more of a secret code shared between potential connections. “I’ve been in line for coffee and a woman will see my Margaux [from the Row] and go, ‘Oh, I know that bag.’ Then we’ll chat.” Graves moved from Atlanta to Manhattan in 2023, and says she’s made some new, local friends thanks to these “bag chats.”

I had my own bag chat that night, when I brought Khaite’s Olivia—a slim crescent of shiny maroon leather—to a house party thrown by a rock star I’d never met. In fact I knew hardly any guests, but as I stood in the kitchen, a woman in vintage Chanel pointed to my bag and asked, “How did you get that colour? It’s sold out!” Before I could tell her my name, she told me the make and model of my purse. Then she laughed about her ex-boss, a tech billionaire, and encouraged me to buy some cryptocurrency. The token I picked surged nearly 30% in about a week. Now I was onto something—a status bag that might bring not just status, but an actual market return.

Thanks to their prominence on social media, certain bags have gained favour among Gen Zers. “TikTok and Instagram make some luxury items even more visible and more desirable to young people,” said Goor. I experienced this firsthand on a stormy Saturday morning, when a girl in a college hoodie pointed at my Miu Miu Wander bag as I puddle-hopped through downtown New York. The piglet-pink purse is a TikTok favourite seen on young stars like Sydney Sweeney and Hailey Bieber. “Your bag is everything!” yelled the girl from the crosswalk. “Thanks, can I have your umbrella?” I shouted back. She laughed and left. My Wander had made a splash—but it couldn’t keep me dry. I ran to the subway, soaked. The bag looked even better wet.

Changing the Status Bag Quo

Everyone loves an ingénue—fashion insiders included. Perhaps that’s why at Paris Fashion Week in September, newer handbags from Bottega Veneta and Loewe jostled for space and street-style flashbulbs.

“These bags, especially ones by independent labels like Khaite, are quieter signals of cultural access,” explained Goor. “Everyone knows what an Hermès Kelly bag is. So now there need to be new signals” beyond traditional status bags to convey power.

Sasha Bikoff Cooper, a Manhattan interior designer, says there’s a less cynical explanation for why these bags have captured celebrity fans—and more important, paying customers. “They’re fresh and also beautiful,” she said. “Hermès is always classic. It’s like a first love. But you want newness, too.”

The Wall Street Journal is not compensated by retailers listed in its articles as outlets for products. Listed retailers frequently are not the sole retail outlets.