Nike ‘Jailwinds’ Are the Crown Jewel of Australia’s Prison System

The first time I heard about the Nike Air Tailwind IVs was via my mate Chris in 2006. He’d just been released from Parkville’s Youth Justice Centre for a violent stabbing and was dead-set on “running missions” until he scored a fresh pair of Jailwinds. “These shoes are the only reason I’ll ever run from a fight,” Chris told me jokingly. “Not because they’ll get taken, but because there’s no way I’m getting blood on ‘em.”

When the Tailwind IV’s were released in 1999, they were the first of the line to reveal the air-bubble windows throughout the whole shoe: emphasising, with plastic grandeur, everlasting comfort. The Air Max technology was revolutionary in the world of running shoes. But Nike didn’t anticipate the legacy of the Jailwinds in the penal colony.

The Tailwind IV’s, or Jailwinds as they were known on the inside, became the crown jewel of the Australian prison system, and anyone who was “heavy in the system” was rocking a pair.

When they first hit the market, Jailwinds carried a hefty $250 price tag, way out of the reach of most in the suburbs. Unless you were a violent stand-over man, most of the kids in the area were lured by the fast-cash prospects of petty crime. You did whatever it took to rock a pair. The stakes were high because they weren’t shoes anymore—they were an emblem of gutter royalty. The Jailwind legacy was laced in half-truths, after-school whispers, and jailhouse mythology passed down from the older boys.

The etymology of Jailwinds remain aggressively contested inside and outside of prison. Some say the shoes were labelled Jailwinds because the lines along the side represent prison bars. Others say it’s because they were the most stolen shoe in Australian shoplifting history. Others believe it’s because they were the first Air Maxes available for purchase in the prison canteen, or because they’re now so rare in the boob that if you cut laps wearing a pair you instantly acquire the status of royalty.

Last month, Sneaker News announced that Nike will be re-releasing their original Air Max Tailwind IV in 2019. So I spoke to some people about their Jailwinds, and what the shoe means in Australia.

Dave / 34 / Barwon prison

VICE: Hi Dave, do you remember the first time you saw Jailwinds in prison?
Dave: It was in Port Phillip, Scarb North around 2004. This young bloke from Sunshine had been lobbed into our unit, and the only way you could get [Tailwinds] in prison was if you wore them when you got arrested. He would’ve lasted all of half-an-hour before one of the Albanians told him to take them off or else he would get his stomach cut open with a hedge trimmer.

But you had (and kept) a pair in prison. How’d you manage that?
Back then, the only way you could get them was if someone wore them in when they got arrested, or if you could swap them off the feet of a mate who visits you. The guards wouldn’t notice back then, but nowadays they’re onto it. You gotta realise that in jail inmates can only be picked apart by our shoes or our hair cuts, so when someone’s got shoes no one else can get, fuckin’ oath it’s a status thing.

Yeah so how did you get your pair?
I don’t kiss and tell mate. But look, I tried to be fair and I offered to swap for a strip of buep [Bueprenorphine] but he misbehaved. So his time took a turn for the worse.

How risky is it wearing a pair in jail?
You’re going to be tested for them. If you’re not in with a group of boys and no one knows you, it will be a free for all. Someone will get you, it just depends who. And if you don’t take them off, you could get slashed, bashed, stabbed, or worse. Who knows.

What did a pair of Jailwinds represent in jail?
Back in the day, the old school blokes who wore them just called them Air Maxes. Everyone wanted them because they were so comfortable and in jail there’s nothing to do all day but cut laps of the yard and stretch the legs. We’re on our feet all day. So you want to be in something comfy.

These days, the fashion is Asics Kayanos and Nimbus. Only the young guys still wear Nikes, but they don’t understand that when we were wearing them it was because they were the best runners. I don’t think they are anymore, and that’s why you will never see anyone who’s done a brick [served 10 years] wearing Nikes. But the young guys see what we were probably wearing when they were looking up to us and try to replicate that look.

To me they catch that era of jail life in the 2000s. Back then the buep was rampant, a point of shard kept you going for days, and anyone who talked to cops copped it hard. When we were rocking Jailwinds it was hard jail mate, and that’s why I think they are the iconic boob shoe.

Who is still rocking them?
To be honest, they’re only popular among the young guys doing graffiti and that in Barwon. No one else really gives a shit about them anymore, they’re just too old and there’s not many around. I think in the last few years, I would’ve seen three blokes wearing them and one of them didn’t know they were Jailwinds. But he’s an old boob-head [prisoner] who still calls them Air Max and rolls around St Albans with a tomahawk stuffed down his pants.

Lloyd Wellington / 29 / Photographer

Hey Lloyd, do you remember when you copped your first pair?
I got my first pair of Jailwinds as payment for a drug debt. Years later my friend tried to buy the shoes back off me, but I will never part with them. I will wear them until the bubbles pop.

What did the Jailwinds represent to you, growing up?
I have always associated Jailwinds with crime. From boob heads, drug dealers, and graffiti writers they were the shoe I would see people wearing and know they were up to no good.

Who was wearing them?
The first people I saw wearing Tailwinds were older graffiti writers or lads hanging around the city or local train station usually fresh out of jail. They had the appeal of the shoe saying: “stay the fuck away from me, don’t look at me.”

What did they represent in Australia?
Jailwinds in Australia represented to me a prison style worn on the street, as well as drugs and antisocial behaviour. They were worn a lot in the graffiti scene from the more raw writers.

What did you like about them?
I have always liked the hard style look of them and the attention they get. They are also very comfortable and practical for any situation. They were a good everyday shoe, even with the stigma attached to them.

Bonnie / 27 / Social Worker

Hey Bonnie, what’s the story behind your first Jailwinds?
I lived in a homeless refuge for a few years, and when one of the housemates moved out they left me a parting gift of the most thrashed and ugliest colourway Tailwind IV’s you’ve ever seen. I’ve still got them.

Throughout your youth, what did the Jailwinds represent to you?
Status, cause you weren’t going to step to anyone wearing them, and as an identifier. If the guy at the bus stop next to me was wearing them you already know he’d seen some shit and done some shit.

Who was wearing them?
Boob-heads and dads that didn’t know what they represented. There was no in-between either. Dudes that were into sneakers fucked with TNs a bit but didn’t really touch Tailwinds. If anyone else was wearing them they probably didn’t have them on for long: nabbing them off people’s feet was a pretty popular thing back in the day.

What did they represent in Australia?
The lower class, growing up around “Eshays”, and being a part of that culture where everyone would get $400 a fortnight from Centrelink and spend most of it on clothes or shoes that they couldn’t rack. Boobs [ex-prisoners] could be homeless but still be wearing the whitest Ralph polo and newest Tailwinds. As long as you dressed fresh, you were good.

What did you like about them?
They are ugly as fuck, but same as all things “Esh”—people who had nothing took something made by a mass corp trying to capitalise off a different sort of audience, and completely made it their own.

Justin / 21 / Tradie

Hey Justin, who was wearing Tailwinds when you were growing up?
When I was growing up only three types of people would be wearing Tailwinds: boob-heads, writers and old men. Tailwinds are pretty much the stauncher version of a TN. Wearing a pair of Tailwinds or a pair of TNs meant that you either wrote graffiti or you were somehow involved in crime and the scene. You could easily tell if someone was part of the underground subculture simply by looking at the shoes they were wearing.

What came with the territory?
If you were going to wear the shoes you had to be prepared to deal with the trouble that came with them. More often than not you could end up punching on to keep your shoes—at least that’s the way things used to be. Nowadays every man and their dog is wearing a pair of TNs, regardless of whatever they may or may not get up to. The news of the tailwind retro is both exciting and frustrating.

What’s the story behind your first pair?
I got my first pair of Tailwinds seven years ago. I had wanted a pair for a long time: unfortunately back then we didn’t have Facebook groups like TN Talk so they weren’t as easy to get your hands on as they are today. Luckily I knew a bloke getting rid of a worn pair so I was in luck. I took the tram out to Port Melbourne and snagged them for $80—which, considering the price for a pair of worn Tailwinds today, was a great deal. They were one of the more common pairs: all white with a gradient grey mesh, faded grey veins with a red tick, and bubbles.

How do you feel about the re-release next year?
It’s exciting, as I’ll get some of the colourways that I wouldn’t be able to wear unless I was able to find them and sole-swap them. And frustrating because it won’t just be the real heads wearing the shoes anymore, everyone will have a pair. I’ve always taken a bit of pride in wearing a pair of shoes that most people in the general public wouldn’t be wearing. Oh well, considering their age they probably only have a few years left anyway.

Kelvin / 21 / Designer
Hey Kels, Who was wearing Tailwinds when you were young?
Unlike the TN, the Tailwind never seemed to really take off anywhere in the world except Melbourne and Sydney. Back then, a lot of my older boys and family wore them because they were into the culture. If you saw people wear them back then, you knew they were the crème de la crème at what they did, whether they were getting up or they were pushing.

I still see them pop-up here and there. A lot of the times they’re people who are fresh out [of prison] and those are the shoes that they had waiting for them back home. Heaps of conversations start when I wear mine out sometimes with people saying “Fuck, I haven’t seen those in years!” or what shit they had to do just to afford them then.

What did they represent in Australia?
I understand you wrote a previous article called “Nike TNs: Australia’s Most Fuck You Shoe” but personally to me, the Tailwind deserves that title. The Tailwind was like the TNs underrated cousin that was only appreciated by a select few. I feel like for a lot of people in Australia, they represented the early 2000s back when things were very different and simpler. Back when being a part of the culture was purely for yourself and not to show off.

What’s the story behind your first Tailwinds?
I got pretty lucky: one of the older boys who I remember wore them back in the day had a pair collecting dust. Before me hitting him up, he would never think of parting ways with them regardless of who asked. It was basically an ode to his youth. After a bit of back and forth I managed to get them for around $180, which was a steal compared to what they go for today. I actually felt pretty bad and sorted something extra after finding out he was going to Masif later that night.

Throughout your youth, what did the Tailwinds represent to you?
The Tailwind represents a simpler time of my youth, before the internet and all the bullshit. Tailwinds were something that one of the boys would put you onto; you didn’t just scroll through Instagram to figure out what the most hyped release would be or what your favourite influencer was wearing. It was really based around the idea of if you knew, you knew, and the Tailwind was the shoe that was never intended for us at its price point but belonged to us entirely.

I was about 14 when the Tailwind disappeared. Rumours were that the mould was lost or the factory that made them caught fire. I feel like I was the last generation to understand how hard the Tailwind shook the culture and lifestyle surrounding owning Air Maxes. If you rocked Tailwinds or TNs then, you were into graffiti, rap music, and getting into trouble just like everyone else who wore them. There was no other substitute. These were more sincere times where the internet didn’t define us and belonging to a subculture actually meant something.

Nowadays, the internet has definitely watered things down. Any kid with an internet connection and the right amount of money can buy them and claim that they were really about it back in the day. With this being said, I’m genuinely curious to see how the Tailwind retro shakes things up next year.

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