I’ll be 36 next month. This became very clear to me over the weekend while shopping in SoHo. I was perusing the selections in some boutique streetwear shop – because, why not? – when I realised I’d walked into a store designed to make men my age feel especially out of place.
It was one of those stores whose sales floor is basically just exposed concrete, with six carefully curated hoodies hanging like sacred relics. While waiting for my obviously-not-gay husband to try on some silly trainers, I caught sight of myself in the mirror. I was holding up a graphic tee featuring some obscure skateboard brand that I didn’t recognise wearing skinny jeans and a frown on my face.
Around me were swarms of clearly twenty-something boys speaking fluidly in Supreme, debating which brand was the holy grail of streetwear while I stood there looking like an impoverished Noah playing at their game. The bass was pounding.
The employees resembled a freshly-thrifted Supreme lookbook, and I suddenly felt very Will Farrell in Old School when he walks into the straight-edge kids’ surprise birthday party. “Can I help you find anything?” one of them asked, breezing over to attend to me.
It was a skinny boy with flawless skin and a blown-out buzzcut who was born the year I took freshman comp. There was some implicit judgment in his question that I’ve come to recognise over the years whenever people my age enter spaces dominated by folks half our age – the subtle eyeroll of, “are you lost?” or “why the hell are you here?” Mourning faces mirrored around me as I muttered something about “just looking, thanks” and shuffled back out to the main street defeated by my three-andsomething years. But out on the pavement, I had a quarter-life crisis.
When had I suddenly become too old to shop at stores like this? Was I destined to a life of plain straight- fit chinos and basic quarter-zips from here on out? Did trying to add even the slightest sprinkling of streetwear-inspired garments automatically make me look try-hard or pathetic?
Lord help me if my age had already ruined my ability to enjoy an entire aesthetic. I stewed in self-pity for three city blocks until I saw him. He was wearing jeans so dark they were black, pristine white trainers, a vintage-style graphic tee under an oversized blue blazer, and a statement watch.
His outfit screamed streetwear disciple but the overall effect was totally age-appropriate and sharp-looking. I realised then that my problem wasn’t that I wanted to add elements of streetwear into my rotation – I was going about it all wrong. Trying to dress like I was the same age as those walking around these stores wasn’t going to work for me.
I had to embrace my age and adapt the aesthetic to suit my life now, rather than mimicking people half my age who likely didn’t have nearly as much invested in their wardrobe as I did. I spent the rest of my walk home cheering myself up by cataloguing all the dudes I saw who had seemingly mastered this delicate balance. How were guys my age – and older! – rocking streetwear-inspired outfits without looking like they belonged in a streetwear store?
I interrogated men I met at industry events (“Hey, how’s your day going? Oh… and what’s your secret with these jeans?”), people I passed on the subway (hey, it’s not stalking if they can see you, right? ), and ran extremely scientific Instagram searches. The conclusions I came to have been enlightening, if not life-changing.
Allow me to introduce you to some rules I’ve devised for the over-30 streetwear aficionado that want to dress modern without screaming “LOOK AT ME AND MY YOUTH-CULTURAL REFERENCES!” Rule #1: Context is everything My first major realization was this: you have to approach streetwear-inspired garb differently at 36 than you do at 23. I can wear the same graphic tee as a 23-year-old skater boy, but it will never read the same way. It didn’t use to bother me, but a certain quote keeps coming back to mind whenever I think about this nugget of streetwear wisdom: “With great power comes great responsibility.” You can wear the clothes of youth culture when you’re older, yes.
But you have to wear them responsibly. What does that look like in practise? Let me introduce you to Eric.
Eric lives in LA, is 41 years old, and works in creative directing. He’s told me on multiple occasions that he loves throwing streetwear-inspired – and sometimes straight-up streetwear – items into his wardrobe. The key, he said, is that he never wears a streetwear full outfit.
He’ll throw on that Supreme shirt, but with dressier trousers, not cargo. He’ll wear his limited-release trainers with high-end denim and a cashmere jumper, not basketball shorts and a hoodie. “Streetwear has always been about taking bits and pieces that I appreciate and incorporating them into my wardrobe, not just throwing on an all-hyper ded outfit because I can,” Eric said. This might seem obvious, but there’s a reason why those 22-year-olds can get away with wearing head-to-toe streetwear and proudly proclaiming they’re wearing “streetwear.” They literally look like children trying to dress themselves.
We know better. We have jobs, responsibilities, a social group that understands Twitch. When we drop knowledge, people listen.
So when we wear streetwear-inspired clothes, we need to think about how to make them work for us. Rule #2: Less logo, more quality If you spend any amount of time around dudes with a vested interest in streetwear, you’ll notice one very obvious trend…the older guys care a lot less about the logos. When you’re young, the logo is the whole damn point.
It’s tribalism. It’s your membership to this specific youth-driven scene. That Supreme box logo or that Bape camo print isn’t just there for aesthetics, it’s a signal to anyone who recognizes the iconography that you belong.
But as you get older, your relationship with logos should become less about wearing your favourite brand as a billboard and more about how the pieces work for you. Think of it this way: last year I bought a hoodie from one of my favourite streetwear brands. It was expensive by most standards but I’d been saving up for it and decided to blow my monthly clothing budget on it.
There was only one problem. It had the brand name plastered across the front in enormous lettering. It’s not that I didn’t like the hoodie.
On the contrary, I loved it and still wear it sometimes. But every time I put it on, I felt silly wearing it in public. I felt like everyone was asking “Why is that older dude wearing a hoodie with that ridiculous logo plastered all over it?” when I stepped outside.
I was proudly wearing a hoodie that screamed, “PLEASE LET ME BE YOUNG AND RELEVANT AGAIN.” Instead I’ve traded that hoodie for another similar one from the same brand in a heavier material with just the logo embroidered on the sleeve. The difference in confidence I have wearing it is worlds apart. Same goes for trainers (quality over colorways), shirts (clever art prints rather than corner-store logos), you name it.
Older dudes gravitate toward brands that allow them to wear streetwear-inspired clothing without carrying all that extra youth-cultural baggage. Japanese streetwear brands like Visvim and nonnative are perennial favourites for this reason. Rule #3: Keep streetwear as accent pieces This may sound crazy, but during my walk of existential despair I started quantitatively analysing how many streetwear-esque pieces the dudes I saw were wearing in a given outfit.
What I found was pretty consistent: the younger the wearer, the more streetwear they were packing on. But every older dude I saw who pulled off streetwear-esque attire, did so by limiting their “streetwear stuff” to one – maybe two – pieces per outfit, with more classic clothing rounding out their looks. “I don’t wear streetwear-themed outfits like I did in my twenties anymore,” my coworker David, who just turned 38 but is still photogenic enough to be featured in street style blogs, told me. “Sure I’ll wear a pair of boutique trainers, but I’ll keep the rest of my outfit pared back. Say I wear a graphic tee?
It’ll be under a jacket. But it’ll be a great tee from a brand I actually like. The ratio of ‘classic’ to ‘street’ in my wardrobe has flipped.” David’s street-to-sportswear ratio is something I’ve started calling “considered contrast” – you want enough streetwear muscling in there that others can tell you’re studying what’s happening in youth culture, but not so much that you’re ripping an article of someone’s uniform and wearing it as your own.
It’s a subtle difference, sure, but to my eye at least the guys that master this end up being the ones that stand out from dudes who are literally wearing brand vomit all over themselves. Trust me, I put this theory to the test. I attended a media event last month knowing I’d be one of the “old guys” surrounded by kids half my age.
Rather than my usual suit-and-chinos baseline, I kept things sharp with a classic pair of charcoal trousers and white button up, but threw in a pair of limited-release Nike SB Dunks in an almost-eagle grey colorway. All night I got compliments on my shoes, not because they were garish but because they were unexpected. Rule #4: Fit isn’t one-size-fits-all Here’s a hard truth I had to accept myself: most streetwear is designed with younger men in mind.
It’s looser than the silhouettes of previous decades, sure. But at the risk of getting overly political with my fashion, that clothing is designed with younger, thinner bodies in mind. It looks that way on the models wearing it – which are almost exclusively male models in their early 20s…and probably didn’t have to shoot fivedifferent catalogues in under a month to make rent.
When I was that age I could pull off literally anything. As I’ve got older, I’ve realised that trying to wear oversized-on-purpose everything just doesn’t work for me. Again, let’s use myself as an example.
I weigh about the same as I did when I was in high school. I’m in better shape than most men my age, probably. But my body just doesn’t have the same proportions as the 20-year-old models featured on all the afformentioned streetwear brand’s websites.
When I try to emulate their exaggerated XXL styles, I don’t look artsy and avant-garde – I just look soft. Instead, I pay closer attention to pieces that still give me some room but don’t drown my frame. It’s why I prefer a slightly loose tee to a hilariously oversized one.
It’s why I’ll balance out an oversize top with a slim trouser and vice versa. My friends Alberto – a 46-year-old fashion director – and Miguel, a 44-year-old street-style photographer who has photographed everyone from Splash News’ Ethan Miller to streetwear’s dad Himself, Karim rumble tell me the same rule. “If you’re wearing an extra baggy top, keep your trousers fitted,” Alberto says. “Or vice versa. You don’t want to look like you’re wearing track trousers and a hoodie…you want to look like you’re wearing track trousers and a hoodie on purpose.” Rule #5: Embrace your age, don’t hide from it This last bit of streetwear wisdom should be obvious by now if you’ve read this far: the older streetwear aficionados I came across for this article were nothing if not unapologetic about their age.
They didn’t hide their grey hairs under baggy clothing and dubbed trainers. Instead, they let their age work with their streetwear-inspired outfits. Don’t be afraid to wear that pair of trainers, but wear them with a blazer instead of a hoodie.
Wear that graphic tee, but with slim-fit chinos and a classy watch rather than with billowing trousers and a trucker cap. Let those things accentuate your age rather than hiding from it. “You catch people looking at you,” my friend Warren, a 52-year-old retailer buyer with a swagger I’ll never have told me as we bonded over our shared Comme des Garçons PLAY Converse jackets. “Let them know you know you’re getting old, but you also fuck with that new Drop on Fridays.” The older guys I talked to all nodded sagely whenever I relayed Warren’s quote. Because it’s true.
When I owned my age and myplace in the fashion ecosystem, I stopped trying to dress like a young blogger and started dressing like myself. A guy who appreciates streetwear, but isn’t defined by it. Style Evolved After my near breakdown in Manhattan, I purged my closet of all the reactive shopping I had been doing in an attempt to relive my youth.
I kept items that I loved that fit my body well, and filled my wardrobe with classics I could style streetwear-ish if I wanted to. My new uniform?
Straight (but not-too-straight) jeans, a plain white tee from an anomalously high-quality brand, my stalwart chore jacket, and yup, a fresh pair of kicks from last month’s release.
I wore this outfit proudly to another retail event a few weeks later and couldn’t help but walk past that streetwear shop I tried on accident. The same kid from that Sunday afternoon was manning the register, looking twice my age despite probably being my son. He looked me over for a long time, and then smiled as he nodded in approval. “You like that jacket?” I asked.
He furrowed his brow, thinking hard. “Where’d you get it?” Was this stolen shopping redeemed? Probably not, but hey. At least I understand my streetwear place in the world now.
To all my fellow over-30 dudes panicking about whether they’ve aged out of streetwear: you haven’t. But you also don’t need to dress like you did when you were actually in streetwear’s target demo. There’s a happy medium in between that lets you scratch that streetwear itch without looking like you’ve got a mini-highlighter hanging from your pocket.
Trust me, you’ll feel cooler than ever once you figure out how to crack that code. You just might have to grow a few grey hairs first.
