Interview: Homeless Fashion #1

Amy Silbergeld
7 min readOct 9, 2020

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This series features interviews with people experiencing homelessness. The following is an interview with Jon, a currently homeless man in his mid-20s.

Vivienne Westwood’s fall 2010 menswear collection

How do people dress when they’re experiencing homelessness? How do you dress, and how does being homeless impact your style?

The way homeless people dress tends to be based a lot more in necessity than in style. There are a lot of factors limiting a homeless person’s wardrobe. Maybe the most obvious of all of these is price. I don’t remember the last article of clothing I got from anywhere other than a thrift store, but it must have been at least several years ago. Every now and then someone I know would boost some nicer clothes though, so sometimes I’ve gotten some nice clothes that way. For anyone that doesn’t know, that’s where they’ll shoplift stuff and then sell it on the street for half of its retail value or an equivalent amount of heroin/meth. Another important factor is space. I’ve been luckier than most homeless in that I’ve usually lived in a van, but I still had to be able to pack all of my clothes into a couple of bags.

There’s also the fact that when you’re homeless, it’s just kinda inevitable that you’ll lose everything you own once in a while. This has happened several times to me. Usually it’s because someone steals it, but sometimes it’s because everything I owned was in a vehicle that was towed away. Which is still theft really, just legal theft. Most of these times I’ve managed to hold on to at least a single bag of clothes, but two of these times I had nothing left but the clothes I was wearing. I was lucky to have friends at these times that helped me out and stole some new underwear and socks for me. I’ll steal stuff sometimes too, but I don’t really have the nerve for it.

I guess my typical homeless outfit would be a pair of girls jeans from a thrift store (they always fit better, they never have skinny enough guy jeans) and a long-sleeved dark shirt. Long-sleeved to hide the fact that my arms are covered in track marks, and dark to hide stains. And unless it’s pretty warm out I’ll probably have a jacket too. I’m not really picky about what kind of jacket but I like one that has a lot of pockets. The value of pockets to a homeless person can’t be overstated, and since I usually wear girl jeans that have fake pockets, I value those jacket pockets all the more.

N. Hoolywood’s controversial runway show at New York Men’s Fashion Week, fall 2017

Do you ever dress a specific way in order to avoid being identified as homeless?

Yeah, especially when my hustle used to be boosting. Anytime I shoplifted I would always try to dress a little fancily. Of course that didn’t work that well, and before long I was arrested for shoplifting. But in my mugshot I look pretty fetching in a merino wool sweater and Oxford.

Other than that, I guess I typically try to be able to pass as not being homeless. I try to not look dirty and stuff, and make sure my hair looks decent. And I think I pull it off alright, but I guess I can’t really be sure. I’m sure it helps that I’m young and (usually) clean-shaven too.

Magdalena Frackowiak shot by Giampaolo Sgura for Antidote

There are a bunch of examples of luxury fashion designers incorporating the aesthetics of homelessness into their products. What are your thoughts on this phenomenon? Why do you think rich people are willing to buy these expensive garments intended to make the wearer look homeless?

I think they’re sorta amusing. I think some of the outfits can look kinda cool. I don’t really think that the people that wear them do legitimately want to look homeless. After all, it isn’t difficult to tell the difference between someone dressed in hobo chic and an actual homeless person. I think the look is more rooted in the desire to appear as though they don’t care. But if they truly didn’t care, they would just dress in head-to-toe Goodwill, so I believe it’s a little more performative than that. I think that they want people to know that they COULD dress better, that they KNOW better, but that they just don’t care.

Magdalena Frackowiak shot by Giampaolo Sgura for Antidote

Are you familiar with “oogles,” middle class white teens who basically LARP as panhandlers? What do you think motivates these kids to essentially playact being homeless? Do you think some people perceive being homeless as “cool” in some way?

I haven’t heard that term before, but I’ve heard of the phenomenon. I think they look around and see how shallow and inauthentic the middle-class suburban culture around them is, and they don’t realize that when they appropriate street culture it’s just as inauthentic. I think there’s definitely a perception in some people that homeless people are cool or authentic for like, not living “in the system” and I think a lot of homeless people kinda help perpetuate that idea, because… well, we don’t really have anything else. But if the choices are to be cool and homeless or lame in my own place, I’m always gonna choose my own place.

September 2009 issue of W

How does homelessness interact with criminalized labor like dealing drugs and selling sex?

Homelessness interacts a great deal with criminalized labor. A lot of homeless people engage in full service sex work, but there are other ways homeless people sell sex too. A lot of times people will say you can come over and spend the night, but they’ll imply (or sometimes explicitly state) that you can only spend the night if you put out. I would guess that pretty much every homeless person has experienced this.

I’ve now been sober for a little over 8 months, but for most of my time being homeless I was addicted to heroin and meth, and in the homeless world they’re both more important than currency. Or maybe more accurately, they are a form of currency. Usually meth addicts don’t have to hustle quite as much, because even someone with a pretty big meth habit usually won’t do much more than $10 worth a day (this depends a lot on prices though of course). But with heroin, an average junkie can easily do $50 worth of heroin a day. I typically kept my tolerance pretty low, so I could usually get by on about $20–30 worth of heroin a day, and maybe $5 of meth. To get it I would either go around collecting cans or sell/deliver bags or give people rides.
One way drugs and homelessness really go hand in hand is that as soon as a person gets arrested for possession once, it’s typically really difficult for them to break out of that cycle of probation and getting rearrested. Being homeless it can be really difficult to make it to court, or even to keep track of your documents that say when you need to go to court. And then if you miss court they’ll put a warrant out for you and the next time some asshole cop runs your name because somebody called 911 on you for your camp looking “suspicious” or some shit you’ll end up in jail.

Lindsay Whidby shot by Jamie Nelson

How does the housed portion of the general public perceive homeless people?

Most housed people seem to perceive homeless people pretty negatively. Every now and then I’ve met somebody cool, like someone that will give me water. Or I remember this one time my boyfriend and I were sleeping under the awning of a church and this woman gave us each a hot pocket with extra cheese melted onto the outside of it. It’s cool when people are willing to do little stuff like that, because it can really make someone’s day a lot better. Most people usually tell me to go away or they’ll call the cops though.

Magdalena Langrova shot by Sebastian Kim for German Vogue

If we had a better system and everyone had their needs met, how would that impact fashion?

If we had a better system where everyone had their needs met, I think fashion would be impacted in the same way as any art, or science or technology. Who knows how many amazing artists or fashion designers or scientists or inventors haven’t had the opportunity to realize their passion just because they were born poor, or because they had mental illness that their family couldn’t afford to treat and wound up on the street, or because they fell into addiction and had to drop out of school. So many great minds have undoubtedly died homeless all because they didn’t have skills that were easily marketable under capitalism.

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Amy Silbergeld

Director of the forthcoming short film Tasked (Emotions Unlimited Productions)