Regrettable Purchases of the Last 30 Years

1990: Cowboy Shoes
This pair of cowboy shoes stole my heart when I saw them in the Mervyn’s department store circular. You may be wondering: Cowboy shoes? Picture a pair of cheap brown cowboy boots, then turn off your eyes above the ankle.

At $29.99, they weren’t a steal in the context of my budget, so I polished them right away to keep them looking good. Immediately, the leather finish melted off, destroyed almost totally by the shoe polish. I insisted on being driven back to Mervyn’s. “Look!” I told the cashier. “These are defective.”

“What did you do to them?”

“I polished them to protect the leather.” I was thirteen.

“You’re not supposed to polish these.”

“All leather shoes should be polished before wearing,” I countered. “That’s how you keep them nice.”

“Shoes like these are only made to be worn for a few months, and then they fall apart.” It was dawning on me just how poor a decision I’d made in buying these cowboy shoes. 

“It sounds like you’re saying Mervyn’s sells footwear that the company knows to be defective,” I spluttered. “You’re selling shoes that can’t survive being polished? Once? With shoe polish?”

She gave me my money back. I bought sneakers.

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1995: Russian Army Surplus Coat 
This navy woolen overcoat spoke to me from the rack at the Army-Navy surplus store in downtown Providence. I’d never lived in a place as cold as Rhode Island turned out to be by early November of my freshman year of college. I was 17, had no proper coat, and hardly any money. This was before the internet and the Providence Mall. If you wanted underpants, you could buy them at The Gap, or take the train to Boston. But I wanted a coat. 

Brass buttons, wide lapels, thick navy wool, huge pockets: It appeared to be the warmest coat in the store. It would have hidden my cowboy shoes had I not returned them. I bought the coat in a rush for $20. Walking back up the hill, wearing the coat, I realized it drowned me, dwarfed me, made me look like a defendant on their way to being tried at The Hague. I struggled around campus in it all winter and then hung it out on a railing to meet its next victim.

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2000: Italian leather coin purse 
This black leather coin purse resembled a miniature doctor’s bag. I’d spied it in the accessories section of the downtown Portland—Oregon—Nordstrom. All fall, my best friend Michaela and I had been gleefully plotting what we’d do with our extra money once Y2K hit and erased our college loans. It was going to be a party, or so we hoped—but you know what happened next. 

The week after New Year’s, I was back in Portland at my depressing tech marketing job in the Pearl District, back when that neighborhood still had unpaved streets. Every day was a slog of rain, eating black beans alone in my studio apartment, and avoiding accidentally sticking myself with somebody’s used needle on my way to work. 

In an effort to cheer myself up, I bought the coin purse for $85. I knew it would make me feel like an adult, a responsible one who carries a receptacle solely to store coins. Instead, it made me feel foolish. 

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2000: Gray 1988 Volvo 240DL 
This hunk of steel cost $3,000 at a used car lot in Southeast Portland. On a pound-per-dollar basis, it was an undeniable deal. Its standard transmission suited my need to do things the hard way. Slightly less standard was the push-button “turbo” fifth gear. You didn’t shift manually into fifth, the salesman explained, but just pushed the pleather-ensconced button atop the utilitarian-but-intellectual gearstick. Wow! 

I was heading back to the East Coast again, this time to get a degree that would let me get a job that didn’t have to do with making money, because making money is for people who lack imagination. As it turns out, making money may also be for people who buy 12-year-old Volvos, because this is a car that needs a lot of love, and by love, I mean mechanical attention and expensive parts. 

My dad and I headed to Rhode Island via the Columbia Gorge, Idaho, and Western Montana. Around St. Regis, Montana, which despite its name is not a haute locale, my dad shifted with extra oomph and ripped the pleather handle completely away from the gearstick, now trailing colored electrical wires. The car would still go, but only up to fourth gear, and we still had 2,600 miles to drive. Deflated, we coasted into the parking lot of a motel with a room for us, a room with a big hole through the door that a recent guest had punched with a fist, or maybe a head, or someone else’s head. 

In the morning, the betrayal of the electronic fifth gear made itself fully known. I stretched the wires as far as they would go, then used duct tape and two plastic straws to suspend the handle in a position that accommodated the electronic connection. Shifting awkwardly, gingerly pressing our way into fifth gear, we made our way to Rhode Island. Eventually, I traded the Volvo in for $500 toward a used Honda CRV. 

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2020: Instagram Neck Hammock
Back in the salad days of the pandemic, I saw an ad on the ‘gram, which I use solely for doing important business research for my various side hustles, demonstrating how I could cure all my back and neck pain with a hip-looking sling called the Neck Hammock that—super wow!—just hangs from a doorknob, and then you put your head in it, and it fixes all your problems. People are so clever and come up with such great stuff. So, I pressed two buttons and ordered it for $36.54.

A foggy number of weeks later, an overseas package arrived with a thin, flaccid bungee cord and a piece of gray plastic resembling the floor mat mechanics place on the floor of your aged Honda CRV before they perform the motor-vehicle inspection. I slowly recalled the fabulous neck-traction device from Instagram. 

Attaching my new car mat to a doorknob in my bedroom-cum-home office-cum-therapy space-cum-recording studio, I tried tractioning my neck therapeutically, but my head simply made its way gently to the floor. I’d been fooled. I could tell you a long story about how I asked for my money back and endured a series of increasingly ridiculous customer-service emails. The Neck Hammock people can afford to pay someone to correspond at length with credulous folks like me, because they are making bank pretending to have invented a miracle product.

Uncharacteristically, I gave up.

The other day, I saw an ad on Instagram for a mattress that replaces your air conditioning, and I was completely wowed. But then I remembered the Neck Hammock. Progress? ❏

Katharine Hill lives in Brooklyn with her family and tiny dog, Old Salty the Bellhop.