Our wardrobes have a story to tell. Open them up and there’s the shirt from that unforgettable party, the shoes from one of our most memorable holidays and perhaps a cherished heirloom from a loved one. These stories we wear are reminders of special people and lovely times. Clothes can hold particular significance as ways to understand and remember people, and to understand ourselves, too. We saw it played out (no spoilers) to devastating effect earlier this year in season two of The Last Of Us. In this way, what we wear can be more than just functional; it makes us feel. We spoke to five stylish men about some of the most treasured pieces in their wardrobes…

Which item in his wardrobe does Sir Paul Smith believe he will be remembered for wearing? “I suppose it has to be a navy suit,” the iconic British designer says. “It’s a classic timeless piece that’s adaptable to all facets of your life.”

It’s so much a signature of Sir Paul’s that it’s become his uniform. “I wear an iteration of a navy suit every day,” he says. “But of course, in true Paul Smith fashion, the ones that are lined have a pop of colour.”

Another item that speaks to his story isn’t a piece of clothing at all, but a camera bought by his father for his 11th birthday in 1957. “It was the first time I’d ever thought about looking and seeing,” Sir Paul says of the Kodak Retinette. “Seeing things through the little viewfinder, which makes you look more carefully.

“That’s something that has helped me in my job over the years. Buying film was expensive, especially when you were 11 years old and only had pocket money. You had to think harder about every picture you took. For me that was the birth of being creative, without actually realising it.”

Teo van den Broeke knows a thing about style as story – he’s written a whole book about it. “For me, clothes have always been a conduit for memory,” says Esquire UK’s editor-in-chief, whose memoir, The Closet, tells the story of his coming of age and coming out through his clothes. A pair of ill-fitting suede Gucci loafers, for example, bring him all the way back to all-encompassing first love.

“I bought them at 14 to impress the first boy I loved,” explains van den Broeke. “He was my best friend, and he was obsessed with magazines and clothes. He’d invited me to go shopping with him one Christmas on Sloane Street and I saw the loafers on the sale rail in Gucci.

“A few months later, I was forcibly outed by another friend, who also told this boy that I loved him,” van den Broeke says. “He stopped speaking to me at that point, which was heartbreaking.”

He kept the four-sizes-too-big shoes, if not the friendship. “The shoes remain in their box at my mum’s house. They still don’t fit and they’re still kind of ugly, but that doesn’t matter. They remind me of being young and in love – and there’s something beautiful in that.”

The Closet is out in paperback on 17 July

The writer and creative consultant Jason Jules once took his beloved watch to be mended by a watchmaker and was advised that rather than repair it, he should buy a new version of the exact same watch as it would cost less. “I said, no thanks,” Jules says.

The reason he holds the timepiece that doesn’t actually keep time dear is because it belonged to his late father. Jules treasures other items his dad wore, too, like a grey and silver necktie from the 1960s. “I never got to see him wear it,” he recalls. “By the time I was old enough to notice these things, my dad was into a more relaxed style of dress. But when I started going out as a teenager, I would rummage through both my dad’s and mum’s wardrobes for clothes.”

Wardrobe finds include his dad’s classic white spread-collar shirts, perfect for the jazz clubs that the then-teenage Jules frequented. But it’s his dad’s modish, skinny tie that he still wears to this day. “It’s one of the few pieces of clothing I still have of his,” he says. “Now he’s gone, I’m beginning to see his life as an entirety and not just as my dad. I can imagine the joy of his youth, the wild times he must have had in the Caribbean and in London in the late 1950s and early 1960s. This tie is a symbol of that.”

Charlie Casely-Hayford wears his signature piece, a gold necklace with pendants by the jewellery brand Alighieri, close to his heart.

“Each carries its own narrative,” the director of menswear brand Casely-Hayford says. “A fish for my eldest, who’s a Pisces; a hand within a circle, symbolising mother earth, for my middle daughter, Gaia; and a lion for my youngest, who’s a Leo. Each symbol represents one of my children, and when I wear it, I carry them with me.”

Gifted to him by his wife, interior designer Sophie Ashby, the necklace tells a story still unfolding. “It marks this stage of life, being a father of three, navigating all the chaos and joy that comes with it. It’s not about nostalgia; it’s about being present.”

The necklace may be light, but it carries huge weight. “The right piece can feel like an extension of you, something that says what you can’t always put into words,” Casely-Hayford says. “This necklace does that for me. It’s subtle, but it holds a lot.”

When fashion journalist Ashley Ogawa Clarke dropped a pair of vintage Ray-Ban shades in the crowd at fashion week, he duly panicked, and with good reason. The black, wraparound 1990s sunglasses were super comfortable, hard to source and the only pair that he never got sick of wearing. But more than that, they meant something to him.

“They were my dad’s Ray-Ban shades,” Ogawa Clarke says. “Beyond how rare they are, it’s cool that I enjoyed wearing something my dad had when he was probably around my age.”

Happily, a kind stranger in the crowd retrieved them, thus Ogawa Clarke wears them to this day. “They remind me of my dad when I was young,” he says. “Maybe it evokes being on holiday together when I was a kid, him wearing them while driving.”

The sunglasses are not just about nostalgia, though. They say something about Ogawa Clarke in the here and now, too. “Style at its best is an external representation of our inner selves,” he says. “It’s a visual language that tells the world who we are, what we value, and how we see ourselves.”