I’ve had the funniest relationship with clothes; I keep losing them. My wardrobe calamities began three years ago, boarding a plane home from England to Northern Ireland. Seatbelt fastened, I realised my favourite sweater was missing. I had, presumably, idly dropped it around the departure gates. But I’d never know. The flight took off. My grey Sunspel sweatshirt with its cute hound dog print was gone, for ever.

Things escalated from there. I mislaid a jacket in Osaka, costly shorts in south-west Ireland, another sweater goodness knows where, and the losses got to me. My mother had become unwell and I was travelling home often, trying to hold on to everything – time, memories, my mum – as much as possible. I needed the everyday to be in its right place when everything else was going so wrong, but if I wasn’t packing and unpacking, I was doing laundry, and in the melee items went awol.

When I interviewed men about the most cherished items they’d lost, it became clear that the impact was more than just a gap in the wardrobe. Yes, the things we lose are often valuable in themselves: a peaked cap that’s the perfect once-in-a-lifetime fit; a pair of brogues so beautiful they ruin every substitute tried on since. But often a trip to Lost Property comes with other baggage. There’s something else we can’t get back: a connection, a memory, a person.

I loved that sweater; but I loved the time before I lost it more. That was irreplaceable.

Introduction by Colin Crummy

The tweed cap: Oliver Jeffers, 40, children’s author and illustrator

There’s barely a photo of me from 2005-2008 where I’m not wearing my Stetson peaked cap. I picked it up in Germany and it was instantly a good fit. I wore an old-time style back then – a peacoat, secondhand second world war boots and grandad cardigans – so the cap suited that.

I am a hat man. My girlfriend’s mum used to think I was bald because she never saw me without a hat. But I didn’t really like peaked caps until I saw this one. It was a herringbone tweed, tannish, in a newspaper boy style, and cost about £70. I wore it from spring to autumn and often in the studio, which became part of the problem. There was a spot of blue paint just on the peak that I had stopped noticing.

I realised the cap was missing as soon as my girlfriend and I got back to New York from a trip home to Belfast. There was a note from the Transportation Security Administration in the top of my luggage saying they’d rummaged through the bag. I assumed the cap had fallen out of the suitcase. For two years, I was shaking my fist at the TSA for losing my favourite hat.

I got married in 2010, which is when my new mother-in-law, Rosemary, came clean. The TSA hadn’t lost my hat. She, in a fit of charity, had tried to get the paint off it in the washing machine, where it just exploded into pieces. She immediately got rid of the evidence.

Rosemary is one of the most kind-hearted, gentle women on the planet, so I couldn’t be mad. She told me her heart sank when she reached into the machine for the ball of fluff. But I was glad to get closure.

The cotton pullover: Diébédo Francis Kéré, 52, award-winning architect

Illustration: Barry Falls/Heart Agency

My father was the village chief of Gando. He was illiterate, so when he received letters he would wait weeks for someone from the city to come and read them for him. In the rainy season, it might take months. In 1972, he sent me, his first son, to school in the city, so I could learn to read and write. I was seven years old.

I was the first child in the village to go to school. When my father told me, I wondered, what is a school? Then I realised I would leave my family and live with my uncle in Tenkodogo, 20km away. The city seemed far from home and dangerous.

I was also the first child in my family to get clothes. In the village, children ran around naked. My father saw that I was afraid to leave, so he bought me a cotton pullover. It cost him a fortune, the equivalent of four chickens. The gift was my father’s way of protecting me, of telling me not to be afraid. At night it got cold, so I used to bring the pullover over my knees. It acted as a second skin. But it also connected me to my family.

I returned home four times a year for school holidays. I’d wear my pullover and all the kids would join me on a little hill in Gando and repeat what I’d learned in school, like the alphabet, which they’d sing back.

The pullover went missing three years later, after it was left out to dry. I assumed someone liked it as much as I did, but I didn’t really know if it had been stolen or if the wind took it away. I just knew I had lost my protection and the connection to my father. I thought, what will I wear when I go back to the village? What will he say?

But my father didn’t punish me. When I returned home, people gathered in the village. My father addressed the crowd. He said that the pullover was old; it was time to get a new one. That I was a good boy and he was very proud. He wanted my education to serve the community, so after I became an architect, I asked the people of Gando to join me in creating my first building, a school in the village, which opened in 2001.

The beige brogues: Tan France, 34, stylist on Netflix’s Queer Eye

Illustration: Barry Falls/Heart Agency

I saw these beige brogues in Office on a break from work at British Gas in Manchester. The shoes stood out: they were the perfect shape, with a rounded toe, a curve to the arch and a higher heel than usual. I’m average height, 5ft 9in, but that extra half-centimetre gave me confidence. It was like I was tiptoeing in them.

The brogues originally cost £130, which was too much for a 19-year-old to afford. But I got the last pair in a sale for £40. I wore them with a pair of slim-fit, indigo Diesel jeans. This was around 2002, when Diesel was hot. The combination was killer. I’d wear them on nights out to Tribeca or Gaia, the dressier bars near Canal Street, where they wouldn’t get trashed. They were the most beautiful, slender shoes; every gay man remarked upon them.

On a trip to New York, I took the shoes in my carry-on luggage to keep them safe. But on the way back, after buying several pairs of heavy Timberland boots, I put the lighter brogues into checked-in luggage to avoid going over the weight limit. When the bag didn’t turn up on the baggage carousel at Manchester airport, I got that gut feeling similar to when you think you’ve lost your wallet. I spoke to the baggage agent and I was so panicked, she thought I was seriously unwell. The shoes were that important to me. They were just so beautiful.

When I see a shoe, I deconstruct it in my head. It comes from spending childhood summers around my grandad’s denim factory in Bury, watching the machinists turn fabric into clothes. After I lost the brogues – which Office had discontinued by this stage – I asked shoemakers in Asia to help me make a similar pair. But they were too hard to replicate. We couldn’t get the specs right. If it had been a piece of clothing, I would have figured it out and made it myself. But making shoes is an art form.

The slogan T-shirt: Hans Ulrich Obrist, 49, artistic director of the Serpentine Galleries

Illustration: Barry Falls/Heart Agency

I lost a lot of things on my travels but my Felix Gonzalez-Torres T-shirt was the dearest to me. It’s about friendship. The designer Agnès B is one of my oldest friends. She made the T-shirt with Felix, a Cuban conceptual artist, in 1994 and it was so beautiful.

It was a very empty T-shirt, blank on the front and on the back it read “Nobody Owns Me”. Felix was a visionary artist. He made these amazing pieces where people could take away the artworks, such as his 1991 Untitled (Portrait of Ross in LA), an installation that is a mound of sweets visitors are encouraged to take from until it disappears. The T-shirt slogan was a statement for personal freedom and independence but also that art belongs to everyone.

Felix’s work inspired the French artist Christian Boltanski and me to create the show Take Me (I’m Yours) in 1995. Created in dialogue with Felix, it was an exhibition where you could touch the art, exchange it or take it away.

Much of Felix’s work, like Untitled, was about his late partner, Ross Laycock, who died of complications from Aids. Felix died of an Aids-related illness in 1996. He was only 38 years old. After that, the T-shirt took on new significance for me. It was an amazing, very personal thing of Felix’s to have and it became a way to remember him. I always carried it with me when I travelled. When my suitcase was lost in transit in 2000, it was the first thing I thought of. Everything else was replaceable. I think about that T-shirt all the time. I wonder where it is. Of all the things I’ve lost, it’s the most significant because it’s about the fact that we lost Felix.

The jade pendant: Christopher Shannon, 37, menswear designer

Illustration: Barry Falls/Heart Agency

The only item that I have been really devastated to lose is a jade Buddha pendant that my grandmother, Joan, gave me during my GCSEs in 1996. Her grandfather was Chinese, so she had an affection for chinoiserie. My mum and aunts and uncles all wore a jade pendant or ring. All my great-aunts’ houses were decorated with Chinese figurines and hangings. This was before Buddhas were as commonplace as they are now; people didn’t have them all over their gardens.

I had heard the story of my great-great-grandfather since I was a kid. Dang Chang came from the Shunde district in China to England for an eye operation in 1899. He opened the first Chinese laundry in Europe, so the legend goes, at 113 Pitt Street in Liverpool.

My grandmother died quite suddenly shortly after she gave me the jade pendant. The morning of her funeral, I discovered that the chain was broken. The pendant was given as a rite of passage and was meant to bring luck. It was our family’s superstition that if the jade broke, it was time to stop wearing it.

But I wore the jade pendant for a while; I was going through my teenage stoner phase, so it worked with my look: black denim with a plaid shirt and Dr Martens boots. When I discovered nightclubs, it didn’t really work with dressing up to go out. I kept it safe in a box somewhere instead but I think someone stole it after a night out. I was really distressed; the pendant was the only thing from my nan, apart from a blanket she made me, and it was special to me because I really loved her. Her sisters and cousins married into other Chinese families but she married my grandfather, who was a barrow boy of Irish decent. The jade was a way of hanging on to her heritage.

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