The rest of us might count our lives in days, hours and minutes, but Mr DeJongh “Dee” Wells, a self-described “kickstorian” and founder of the podcast OSD (Obsessive Sneaker Disorder), measures the passage of time in sneakers, attaching them to moments and memories gone by. He bought his Nike Air 180s two weeks before his 18th birthday in April 1991, just after his father died. His first job? At Boston College in a pair of Air Max 95s in grey and spring green. And when his mother was sick, he stepped into an elevator at the hospital and a doctor complimented his Asics. During the short journey, the pair got to talking about the various orthopedic merits of his footwear. “We’re having this whole conversation, next thing we’re having a conversation about feet. And he goes, ‘How do you know so much about feet?’ And I said, ‘The reason I know so much about feet is because I love sneakers.’”

Growing up on Saint John, the smallest of the US Virgin Islands in the Caribbean, his passion kicked off at home. “Everything started with my parents,” he explains. They were playing one of their regular tennis games and instead of keeping score, the young Mr Wells’ eyes were fixated on one thing: their sneakers. To this day, he can recall the exact models. “Dad was wearing a pair of Rod Lavers and Mum was wearing a pair of Stan Smiths… [I was] mesmerised by the white and green. That’s where it began.”

It followed him to school where, confronted with a strict uniform code, Mr Wells would dream up excuses for why he had to wear sneakers to class and, if his efforts failed, he’d surreptitiously swap his regulation black or brown leather shoes for his favourite kicks whenever he got the chance. “As soon as the bell rang, I would change back into my sneakers because that was the one thing that I could do to be different, but also, it just made me feel better.” The day he realised he could get away with wearing all-black Reebok classics without his teachers noticing, his life changed: “Oh, that was a beautiful moment in time for me.”

It wasn’t until he stumbled upon message boards as an adult that he realised he wasn’t the only one who shared this obsession. Connecting with strangers on the internet made him feel a sense of kinship and he realised the true societal significance of his specialist subject. Confident in his mastery of the history of sneakers, he applied for a marketing job at Nike, but was told he didn’t have enough on-paper experience to interview. “In the back of my mind, I’m going, ‘Well, I feel I know probably more about these sneakers from a cultural standpoint and why they resonate.’ That frustrated me.”

It didn’t deter him, though. Like his mother before him, who was a public school teacher for 30 years, he decided he needed to share the knowledge he’d acquired. So, in 2011, he set up SOLEcial Studies, a pop-up programme of workshops for young people to school them in the intricacies of the sneaker industry and, in some cases, help them to secure their dream jobs. “We’ve always said, ‘don’t just be a customer’,” he says. “You could be a creator, but a creator wears all sorts of different hats. There’s someone that is doing the accounting and finance; there’s someone doing the marketing and storytelling; there’s someone designing the actual layout of the store.” Options, and understanding that there are less trodden career paths in the sneaker business, are what Mr Wells wants his students to take away from his sessions. “Their eyes are open and now they are thinking bigger about the possibilities of what they really love to do.”

He credits his high-school maths teacher with helping him to understand that in order to get through to certain students, you need to make the subject matter actually matter to them. “I wasn’t getting simple calculus and trigonometry because I couldn’t visualise it,” he says. His tutor’s solution was to reframe the question using baseball and American football analogies so it made sense; thus, a question about fractions became a question about batting averages. “He really broke it down. I think that’s so important for a teacher to do, to be able to connect with a young person.”

The same principle applies to footwear, Mr Wells says. “Sneakers can be used to teach any subject. But particularly in this day and age, when people are talking about science, technology, engineering, arts and mathematics (STEAM), they fit into every one of those kind of boxes.” The time is particularly ripe for this attitude, he says, now that, in the space of just a few months, the world we inhabit has altered so drastically. “The days of going to college to get an education, become a lawyer or a doctor or whatever, those days are long gone. With Covid and this pandemic, we’ve seen how that whole educational system has been disrupted,” he says. “Here’s an opportunity now to be a creator, to be a storyteller. If you’re willing to hustle and network your behind off, you can build a brand. You can start your own company.”

You get the impression that, no matter how small a hand he has in it, Mr Wells would consider his life’s work complete if just one of his students ended up pursuing their passion, just as he has. When I ask him if he’s had any specific success stories – young people who have graduated from his programme to bigger and better things – that’s when Mr Wells starts to, for want of a better word, gush. “Oh man, there are so many,” he says, his pride palpable. “There’s a young lady and she’s a footwear designer. I met her when she was in high school in Boston and now she’s at adidas.” Another has won competitions for Puma, while another young man who started his career as a bike courier is now partnering with some of the biggest footwear brands in the business to design messenger bags.

All that being said, that sneakers are at the intersection of creativity, culture and capitalism doesn’t necessarily sit entirely comfortably with Mr Wells. The darker consequences of “drop culture”, in which sneakers are released in highly limited quantities to ensure that demand outstrips supply, have always worried him. But, he says, it’s not a new phenomenon, nor is it limited to Air Jordans, recalling the sensationalised spate of robberies and murders linked to the iconic sneaker’s releases. “There’s always going to be people that want a product and can’t get it and that’s going to add to the hype of it. And sadly, we have people that will kill or hurt others for that same product. It happened in the 1980s and 1990s, and we see it today.”

He’s also apprehensive about whether the big companies, the same ones his former mentees are now working for, can truly act as agents for social change. When I bring up the complicated subject of so-called “sneaker activism” – when companies slap a raised-fist logo or Pride flag on a shoe – he diplomatically asks me to narrow the scope of my question. “I do look at it with a bit of cynicism,” he says. “[But] maybe it starts a conversation. Maybe a young person buys that sneaker, wears it, and Mum and Dad ask the question, ‘What’s the deal with those?’ And they have this conversation and maybe that’s their moment to come out to their family.”

He points out that people have been customising their sneakers with political messages for decades before companies got in on the action. “The Black Panther party was doing it back in the 1960s,” he says. At the recent Black Lives Matter protests, which Mr Wells helped coordinate locally, he noticed some of those marching had followed suit, and he hopes it’ll lead to conversations internally at big sportswear brands about their own responsibilities and role in addressing systemic racism. “They realise that they built their base off of black culture. But yet when you look at their executive teams and boards, there are not many black or brown people in those higher level positions.” As a black man himself, he says, those discussions are more urgent than ever right now. “I mean, a big reason we’re having these issues right now regarding racism all across the board is because we’ve hidden from it. We refuse to talk about it.”

Just like they do in the classrooms he visits and workshops he holds, Mr Wells believes sneakers can play a part, however small, in starting wider discussions and debates about the society we want to live in. “At the end of the day, all we are as human beings are storytellers. That’s what we do. We live, breathe stories and we share these stories,” he says. So, the world would be a better place if we all talked about sneakers more? “Yeah,” he says. “Let that be the starting point.”