I first thought about buying a new jumper (what Americans call a sweater) on New Year’s Eve, as I walked into a friend’s apartment for a couple of drinks before curfew. It was one of my first evenings out in Milan since my homecoming: I was born here but spent most of my adult life abroad, and when I came back in late December 2019, it was only a few weeks before the local Covid-19 outbreak. 

I spent the evening wishing I’d worn something else. I looked sheepishly at my friends’ turtleneck jumpers, shiny dark blazers, and perfectly slim-fit shirts, and hoped they didn’t notice the ensemble I’d tossed on. My dark blue jeans were once neat, but their hems had become frayed over the years. The white and gray striped shirt fit me perfectly when I bought it in 2014 but the fabric had since stretched and stiffened. As for my red jumper, it was just too red and too bright. “I should take better care of myself,” I remember thinking, and I set out to buy a new jumper.

The search morphed into agony. I wasn’t after anything fancy: A smart-looking, no-frills, plain-colored jumper would do the trick. But for weeks, I scanned half a dozen sites without making the purchase. I tormented my girlfriend, soliciting her opinion about the tiniest details. 

I copied and pasted the URLs of a handful of jumpers I liked onto a sticky note on my laptop, with information about their price, available sizes, and color. I returned to those pages at least once a day, musing about which ones would fit me better, checking if there had been any price reductions, making sure my size was still available.  

Several times, I added a jumper to the cart and hovered over the “Pay now” button, but something would make me question the purchase and prevent me from buying. What surprised me was not so much the overthinking as the familiarity of that behavior — I’d gone through iterations of the same block several times, and the discomfort of the experience had made me stop trying. This was the first jumper I would buy myself in about six years.

I can remember a time in my life when buying clothes came easily to me. The chests of drawers and wardrobes at my parents’ place are still full of the stuff I hoarded as a teenager, when I changed styles every other year: the baggy hoodies and low-crotch jeans I loved when I was 13 and 14; the chunky skateboarding shoes and skinny pants of my mid-teens; the leather jackets and rock band T-shirts I wore at age 17 and 18. I continued through my early college years, when, to impress people at parties, I stockpiled T-shirts with graphics I once found funny but now make me cringe.

I don’t know for sure when things changed. I know it wasn’t an abrupt shift and that it began years ago. I first became aware of it in 2014 during an internship in China, when my boss, a Brit, noted that I looked quite “scruffy” compared to the Italians he knew, let alone the residents of Milan, a city widely considered to be a global fashion capital. 

It was a time in which I moved frequently to chase education opportunities, work experience, and absurdly high self-improvement goals. I spent years bent on trying to master Mandarin. (I failed.) It built anxiety, which I eventually began to talk to a therapist about during the pandemic.

And all the while, I left behind the way I looked. I began looking in the mirror less and less often. In several family photos, my hair looks unkempt and overgrown, a feat born out of the fact that I insisted on cutting my own hair but hardly ever sat down to do it. I seldom bought any clothes, and when I did, it wasn’t to look better, it was to fulfill an unavoidable practical purpose. When the sole of my shoes came loose, I got myself some new ones. When I moved to the UK, I bought a warmer waterproof coat. If the pockets or crotch of my jeans had too many holes, I bought a new pair.

The last jumper I remember buying was at a fast-fashion retail store in 2015, as I prepared to start my master’s. It was a cheap, slightly oversized, dark blue cotton and wool jumper for about €20, although, to be honest, I can’t remember if I paid for it myself or someone else gave it to me. It is still in my wardrobe today, shabby and partly covered by lint balls.

Now, to be clear: Other people have occasionally bought me clothes, preventing my physical appearance from being left completely adrift. I currently own two sweatshirts — one gray, one green — and both are presents from my girlfriend. She also gave me the fanciest jumper I currently own, a woolen quarter-zip dark blue pullover, as a Christmas present two years ago.

My mom also sometimes bought me clothes, although she would often pick items several sizes too larger, as though I still had to grow to fill them out. In 2018, she gave me a green vest that would fit me only if I gained 30 pounds; in 2019, a leather jacket whose sleeves were long enough to cover most of my hands; in 2020, size L Scooby-Doo pajamas.

It’s hard for me to say why I never bought clothes. Some may praise my behavior, believing it to stem from an unflinching ethical conviction — a sort of epic stand against consumer culture and the fast-fashion industry. Or you could think I developed a taste for a scruffy-looking clothing style, one that creates the appearance of carelessness but where a lot of attention is paid to the choice of baggy clothes and worn-out jeans.

But neither is my case. For years, I considered buying and intended to buy clothes — and several times I spent entire half-hours in retail stores and online shops — but I invariably steered clear of purchasing. I never thought it would be worth the money and the hassle to buy an object whose sole purpose was to make me look better.

It was only earlier this year, long after the New Year’s Eve drinks sent me meandering on the internet, that I began thinking about the reasons for my block. One day, after I got stuck procrastinating in the wait for a price reduction that would never come, I mentioned my newly found habits to the therapist I’ve been speaking to. He wondered why.

 “What impression do you get from people who don’t look after their physical appearance?” he asked.

“Unkemptness?” I suggested.

“Distress,” he said.

That was why I didn’t have anything nicer to wear on New Year’s Eve.

My neglect for myself ran deeper than the buying block I faced with this jumper, perhaps fed and augmented by the pandemic’s grip on social life. Since we were put under new restrictions in the fall, when I go out to see my parents or buy groceries, I throw a coat on top of my pajamas and walk out the door. I hardly ever look in the mirror and often go longer than three weeks without shaving. I haven’t had a haircut in more than two years and have started to tie my hair in a bun at the back of my head, but I comb it rarely and haven’t bought any hair care products. When untied, it falls below my shoulders — ruffled, unruly, frizzy.

I eventually settled on a knitted turtleneck jumper for €44, including a €5 delivery fee. My size was not available for many of the jumpers I was obsessively tracking, and in my fleeting moment of resolve, it seemed to possess most of the qualities I was after. It was dark blue, not black, so I hoped I could match it with several of my other clothes; the turtleneck made it more fashionable than the old jumpers I owned; and the thin layer of silk, cotton, and cashmere promised to be light but warm.

I tried it on seconds after it landed on my doorstep. At first, it felt awkward, like the times I remembered seeing myself after a haircut. The jumper covered most of my neck, making my unshaven beard stand out. It wrapped tightly around my shoulders and chest as if it were a new second skin. When I looked in the mirror, I thought it made me look slimmer, orderly, and perhaps taller, too. It clashed with so many parts of the way I looked — my unkempt hair, the beard — and made them look out of place. It made me look good, and I wasn’t used to it, and I still had so much work to do.

In the next couple of days, I felt an urge to return the jumper. A part of me considered whether it was the best use of my money. Perhaps I really didn’t need a new jumper. And what was more, I had done nothing to deserve one, like I had done nothing to deserve any new clothes in the last few years.

But I’ve resisted that urge, and I’m glad I did. I still go weeks without shaving — three, at the time of writing — and haven’t yet cut my hair. But I’ve been wearing my new jumper a lot to the few social occasions we have: dinner with the family, or a quick hi to some friends. I’ve had it on so much that my girlfriend mocks me every time we go out. “And what are you going to wear todaaay?” she says in a sing-songy voice. Part of me feels ashamed, knowing I’ve probably worn it a few times too many. But another part doesn’t mind the mockery and cherishes the warmth around my neck and silky feel on my skin. It feels less like a piece of clothing and more like a first step.

Alessio Perrone is a reporter and writer currently based in Milan. His writing has appeared in the Guardian, Slate, and LitHub.