The streetwear community attracts enthusiasts of all creeds, backgrounds, and ages. Take for example, Charles Allcroft, a 73-year-old former art history professor at the School of Visual Arts, with a focus on Tibetan and Indian art. Before that, he worked as a performance artist and playwright for 25 years.

In a past life, he created pieces with Jenneth Webster, a former Associate Director at Lincoln Center, and received praise for his play Vintage Wine, or Past Its Prime?, a reflection on age, long creative careers, and the struggle to keep the fire alive to stoke the next generation.

That theme is central to Allcroft's perspective on streetwear. The studied jazz fan melds his academic background with a genuine passion for streetwear that is truly felt when he talks about it.

He discovered brands like Alyasha Owerka-Moore's Alphanumeric, Denim by Vanquish & fragment, and ALIFE after his life in acaedemia, working at The Strand bookstore warehouse. It's a post he held down for 20 years while diving deeper into his second life as a streetwear hobbyist.

“My friend Joseph Lamonica always wore hoodies. He inspired me to read about streetwear and go to places like Dave’s Quality Meat, aNYthing, NORT/RECON, and Memes,” says Allcroft.

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He developed a rapport with some of the shop guys at Supreme's Lafayette flagship, who set aside some pieces for him on drop day. Since he was unable to make it to the shop when they opened in the morning, they set aside a bag with his stuff for him, and he'd come and pick it up at 6:30 p.m. on the dot, every Thursday. So they started labeling his bag as “Mr. 630,” even long after they learned his name.

Allcroft's life has intersected with some of the most influential figures in street culture and fashion as a whole. He recalls a time when he shared an elevator at The Strand with a young, up-and-coming designer.

“Someone told me he was working on his own brand. He wrote the name on a napkin in a freight elevator. Years passed and the brand began doing well,” he says. “It was Hood by Air.”

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His favorite brands range from what people would expect, like Supreme and fragment, to Enyce and COME TEES, a brand he discovered through Venus X's store, Planet X. He also has an affinity for African designers like Jimi King, N'ketiah Brakohiapa, and Moshood.

He has a soft spot for stores like Nepenthes and Mannahatta, and appreciates how ”they honor the design of even a button.” Handmade African  textiles add a worldly accent to the roomy SoHo loft of his girlfriend—the visual artist Annette Weintraub—and actually vibe well with his collection of streetwear, which includes a pair of SNEEZE x Pro-Keds sneakers of which only 200 exist.

As someone who describes his eclectic collection of streetwear grails and African designer gear as ”treasures,” it's evident that Allcroft is a treasure himself. One of the last true free-thinking, self-confident SoHo weirdos (in the best sense of the word) who flies his own flag. It isn't strange to see him holding court at one of the plethora of independent shops in the area. We actually first encountered him at the Noah store, showing off some of his recent acquisitions from that day's Supreme drop, and asking questions about the newest items at the shop.

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It's this combination of curiosity and a lifetime's worth of cultural context that makes him a fascinating person to speak to, and an even more discerning consumer. He waxes nostalgia about first discovering Denim By Vanquish & fragment at San Diego's ACD Gallery, and meeting Alphanumeric founder Alyasha Owerka-Moore.

He misses Lower East Side shop Ale Et Ange dearly, recalling the African-tinged brand as “subtle and elegant, and they made the best caps.” The label shuttered its storefront in 2012, but lives on as a print publication and still produces clothing for private clients.

But he isn't one to live in the past either, as he's impressed by Extra Butter's newly refurbished storefront, just steps away from where Reed Space recently closed its doors. He's particularly fond of the design by Japanese architect Nobuo Araki.

Allcroft's relationship with clothes is reinforced by his numerous travels, too. His love for Hood By Air was further enhanced through an exploration of club culture, which saw him traveling to Berlin, arguably the heart of where electronic music and nightlife meet.

He describes being in the legendary basement “techno dungeon” at Tresor, wondering what all the buzz was about. A friend informed him the experience would probably have been heightened if he too were under the influence of the same mood-altering psychedelics as the room's other denizens.

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“On a recent trip to Tbilisi, Georgia I met the rapper Luna 999,” he recalls. “He and Irina are the designers of LTFR—Let The Funk Ride—the edgy Post-Soviet brand. That was my most perfect streetwear moment.”

He discovered Luna 999 online, and then found himself in the rapper's small studio, halfway around the world. Now, he's an even bigger fan, and is able to talk not just about his music and clothes, but Luna 999's other interests like old-fashioned toys.

One of Mr. Allcroft's more recent favorite stories involves the Supreme x Louis Vuitton box logo hoodie and skateboarder Josh Velez.

“I saw my friend Josh in the Supreme Louis Vuitton hoodie. I told him the top asking price was $25,000,” he recalls. “The next day he took out his cellphone. There he was, in the air, on his board, a red blur against the dark night. He said: ’Times Square, 2 a.m.’ I said someone else would have turned that hoodie into a bank account. He said: ’I wanted to turn it into a memory.’”

He describes Velez as a guy who “comfortably wears bright colors because he is bright himself,” although Allcroft would just say he shines. He saw him again recently, wearing a pink box logo hoodie, and noted that while on many people, the clothes look like they're wearing them, Velez is one of the few people who can absolutely own that look.

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As the shoot wraps, we ask Mr. Allcroft if he has any thoughts on the current state of the streetwear community. His reply was simple, and brings it back to the most important part—the enthusiasts and heads who are invested in more than just the clothing.

“Pryce Holmes of Supreme, Palace, and Alltimers said it best: ’It’s not about the clothes. It’s about the people.’”

Allcroft still loves the weekly drops. He is fan of the energy in the anticipation, although he no longer has to endure it himself.

“If you’re lucky, you score a fire shirt,” he says. “And maybe next week, you can do it again.”

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But for a new generation of streetwear enthusiasts—and those that will come after them, Allcroft offers this sage advice for discovering your personal style:

“The question is why you bought it. Were you following the general energy or following your own mind? If it was your own mind, then you can combine these pieces into something new. Something that wasn’t there before,” he says. “Then there is more than a fire shirt. Now you are fire. You walk down the street and people see you. You shine it back. The world grows brighter.”

Now meet Alexander Jones, who is arguably the flyest postman in New York City.

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