Sneakerhead Mr Sean Conway, of NYC store Kith, explains how buying “one pair to rock, one pair to stock” helped him make a living from his passion .

Just as smell is the most primary sense, sneakers are often a male’s first wardrobe choice. From the time we are boys, begging mum to buy us the pair that will magically transplant us into the cool crowd, we never lose that visceral connection. As we grow older, sneakers telegraph which tribe we aspire to be part of: jock, rapper, rock’n’roller, fashionista.

For Mr Sean Conway, a love of sneakers blossomed into obsession at the age of 13. He can describe his first serious purchase with the same breathy wistfulness that others reserve for their first concert, or their first time. “It was the Air Jordan 4 – that was the shoe that did it,” Mr Conway recalls as we sit in a café adjacent to Kith, the legendary New York sneaker and apparel store where he now works. “It was 1999, I was in eighth grade and this was the coolest sneaker to have at that time. It still remains one of my favourites to this day.”

A veteran of 14 years on the sneaker collector scene, Mr Conway, 28, believes the culture has never been bigger than it is right now. “When I first started collecting, the community was a comparatively small clique of guys and we pretty much all knew each other,” he says. “Instagram changed all that. The sneaker community exploded globally. And influencers including Kanye West and Pharrell Williams have helped sneakers cross over from sportswear into fashion.”

Last year was a major success for Nike, which reimagined its iconic Air Force 1 courtesy of successful collaborations with both Pigalle (a top-end boutique in Paris) and Givenchy’s creative director, Mr Riccardo Tisci, for which MR PORTER was one of a handful of retail partners. Both collaborations sold out within days of release.

adidas also had a strong 2014 thanks to the relaunch of its classic Stan Smith tennis shoe with Mr Raf Simons and the aforementioned Mr Williams, among others. It looks set to build on that momentum after Mr West’s controversial defection from Nike following the huge success of his first two Nike Air Yeezy shoes. His much-anticipated first shoes for adidas are due for release early this year.

The hype around such high-profile releases has vastly increased the demand. “When I was a kid, the lines for new releases would be a couple of hours; now it could be a couple of days,” says Mr Conway. “That just shows how big it’s got.”

The longest Mr Conway has ever queued for sneakers is three days and two wintery nights, sleeping rough on the pavement outside Kith for a pair of Asics designed by the store’s renowned owner, Mr Ronnie Fieg. “I was the 18th person though the door,” he recalls.

Having got to know the guys at Kith, when an opportunity even rarer than a pair of Nike Air Yeezys came up – a job on the shop floor – this time Mr Conway was first in line. As an indication of how highly prized a position this is, when Kith recently tweeted that it was hiring more staff, there was a line of 500 applicants stretching four blocks.

Those who dismiss sneakers as teenage kicks – a childish obsession – overlook the fact that serious money can be made by aficionados who know how to fill their boots. Some people play the stock market. Others dabble in property. A few people still believe pension funds are the way to go. Mr Conway’s life savings are stashed in 500 cardboard boxes, split between his rented apartment in Brooklyn and his parents’ house near Washington DC. Each one contains a pair of ultra-rare, highly collectible sneakers.

“At first my parents thought I was crazy,” says Mr Conway, who grew up in Maryland, 30 minutes from the capital, and worked part-time in his local skate shop as a teen. “‘Why are you spending thousands of dollars on a pair of shoes?’ they’d ask. So I showed them how much I was making by reselling pairs on eBay. Then they understood.”

Mr Conway estimates those safety deposit shoeboxes that now line the walls of his Bushwick bedroom add up to a down payment on a house. “I’ve invested around $50,000 in this collection but it’s worth at least $100,000 right now so I’ve doubled my money – not a bad return,” he says. “And I’ve done it doing something I truly love so it doesn’t feel like work at all. It’s a passion.”

After graduating with two bachelors degrees – one in business; the other in Spanish – Mr Conway took a job he hated. “I was selling valves and couplings – the stuff that water goes through – for a company called Dixon Valve in Maryland and living at home. It wasn’t exactly my dream.” So he quit and moved closer to New York, the epicentre of sneaker culture. And for the next four years he turned his hobby into a full-time job: working for himself, buying and selling sneakers. 

“I was going to all the sneaker conventions, setting up a table, and making maybe $3,000-$4,000 profit in five hours,” he says. “I was on the sneaker blogs all day. I knew everyone on the circuit and everyone knew me.”

These days, Mr Conway is one of the respected elder statesmen at Kith. His girlfriend works at the neighbouring store. “She already knew what I was into before we got together but when she first came over to my place she was like: ‘Sh*t, that’s a lot of shoes!’ So I said: ‘If you don’t like my shoes, you don’t like me. It’s a package deal!’”

This month, the couple will move in together, which means Mr Conway needs to evict Jordan, Stan and several dozen other box-fresh roommates to make space. “Maybe I’ll sell the lot and put together that down payment,” he says. “Better to do it all at once and get a big chunk you can do something with rather than sell it all bit by bit.” He pauses while he considers the possibility. A wince gives way to a smile. “Then again, maybe not.”

“These are the most valuable shoes I own. They are replicas of the sneakers Marty McFly famously wore in Back to the Future Part II. In 2011 Nike released 1,500 pairs in a charity auction to raise money for the Michael J Fox Foundation for Parkinson’s research. It raised more than $5.7m and Sergey Brin, co-founder of Google, matched this, so in the end it generated $11.4m. I paid $3,200 for mine. They would easily be worth more than $8,000 now but I would never sell them, as it was for charity so it wouldn’t feel right. There are rumours of a new release of Air Mags coming on 8 September 2015 – the date the DeLorean landed in the future.”

“The original was a big shoe for me first time around in 1999 and I guess if there was one shoe that kick-started my collection and my obsession, it was this. So when it was retro-ed [re-released], I had to have it. It’s not an expensive shoe; it’s more about what it means to me. Still, this one will have gone up in value from the $100 I bought it for to around $400-$500.”

“This is my favourite ever pair of Pumas – a collaboration with the Australian magazine Sneaker Freaker, pretty much the first ever dedicated sneaker magazine. This is a 2013 re-release of the original 2007 shoe, of which limited editions of 30 pairs were handmade from shark skin. Puma doesn’t use exotic animal skins any more so this is faux shark. We sold them in Kith for $200 and they would be worth double that already.”

“These shoes, known as ‘super greens’, never actually went on sale. They were designed by my boss, Ronnie, the owner of Kith, as a charity initiative and were given out to the kids in Haiti as part of the disaster relief effort following the earthquake there. I’d never sell them – Ronnie would kill me! But on the charity auction they went for as much as $7,000.”

“Nike SBs are skateboarding shoes. Jordans are basketball shoes and are separate to Nike. This was the first collaboration between SB and Jordan. It was made for the skateboarder Paul Rodriguez, incorporates design elements of two or three Jordan shoes and is the only Nike SB ever to carry the Jordan logo. They cost me $80 in 2005 and I’d estimate they’d go for around $500 now.”

“Designed by Kanye West, whose nickname is Yeezy, this is one of the most iconic shoes of my generation. He released two Yeezy shoes, the first in 2009 and the Yeezy 2 in 2012. There were only 5,000 made in each of the two colourways of the Yeezy 2 and the hype was crazy. There was no lining up for this one – it would have got out of hand. I got mine from 21 Mercer [a high-end Nike store in SoHo, Manhattan] by responding to an RSVP on Twitter. I paid face value of $245 but they were immediately going for $4,000-plus on eBay. I’ve worn mine around 15 times and they’d still be worth between $1,500 and $2,000.”

“If there was a fire, the shoe that I would save would be this one. I just love it. The wax stamp on the side is supposed to be like a vintage wine, and 23 is Jordan’s number. It was super limited, just 1,331 pairs, and each is individually numbered on the tongue; mine is 745. I got these from House of Hoops in Harlem back in 2010 for $745. They’re now going for $1,800.”