Not long after Tremaine Emory resigned his position as Supreme’s creative director last summer, he came across an image of an old hoodie from the brand emblazoned with one of its familiar biting slogans: “Illegal business controls America.”

The hoodie is part of the Supreme canon, an embodiment of its middle-finger approach to appropriation, with its use of the signature Futura font lifted from Barbara Kruger; and its flirtation with hip-hop radicalism — the phrase comes from a Boogie Down Productions song.

With his fraught tenure at Supreme in the rear view, Mr. Emory began to see the hoodie in a different light. He’d been hired as its first Black creative director, but his tenure lasted less than a year and a half. He left the company citing structural racism in its ranks, in part spurred by how the company bungled a collaboration he’d secured with the firebrand artist Arthur Jafa.

Supreme, the foundational skate brand founded by James Jebbia, turns 30 this year, which means that it has been around long enough to sow the seeds of its own resistance.

“I respect the legacy,” Mr. Emory said. “That doesn’t mean I can’t question it.”

And so this week, as part of his own brand Denim Tears, Mr. Emory is releasing collaborative pieces with Mr. Jafa very similar to the ones that Supreme ultimately declined to release, owing to their raw and provocative commentary on Black trauma. And he remade the signature hoodie, in the original colors, using the same visual language and cheeky audacity but broadcasting a different message: “Systemic racism controls America.”

It’s a nod and a nudge. A wink and a slammed door. The Denim Tears-Jafa collaboration is, Mr. Emory said, “a dance between ideologies. This whole situation between me and James Jebbia and the Supreme C-suite helped result in this piece of fashion, art and design.”

It’s also a bristling and timely example of how Mr. Emory has, for the past few years, built upon familiar, almost taken-for-granted streetwear vehicles, imbuing them with layered and often unearthed meaning, centering and amplifying Black stories and perspectives that are often alluded to in this sector of the clothing world but rarely deeply explored.

Denim Tears, which began in 2019 as a fashion-art hybrid project, is at the forefront of a handful of rising post-Supreme streetwear concerns — Awake NY, Barriers and Born X Raised among them — not owned and operated by white people. It has been able to scale quickly thanks to collaborations with Levi’s, Converse, Our Legacy and Dior, and its Pan-African flag tweaks on Ralph Lauren designs of the 1990s. But it remains a nimble business, with a different approach to commercial risk than the more established brands that have turned streetwear into a multibillion-dollar industry and which often strategically utilize Black expression as an accent of cool.

Being a key part of this generational change in streetwear has put Mr. Emory in cross hairs at almost every turn, as a symbol of both transformation and representation. At Supreme, he found an insufficiently diverse staff who treated discourse about race like “pushing food around the plate. They didn’t want to eat the vegetables,” he said. The Jafa images he’d wanted to put on Supreme clothes and skateboards, which included depictions of lynching and the lash marks on the back of a former slave, caused discomfort internally and externally. And while leaving Supreme freed Mr. Emory to devote all of his work time to Denim Tears, his current collection, which takes visual inspiration from Black Southern food culture, has been met with online resistance.

All the while, he has been recovering from an October 2022 aortic aneurysm that landed him in the hospital for two-and-a-half months, and happened around the same time he was being attacked on social media by Ye (f.k.a. Kanye West), his former employer, for daring to publicly denounce his White Lives Matter-era antics. For Mr. Emory, whose natural disposition tends to the ruminative and patient, and who for much of the 2010s played creative consort to Mr. West and Frank Ocean, among others, while coming into his own as a clothing designer following the path laid out by his close friend Virgil Abloh, the attention has been dizzying and disorienting, though not quite destabilizing.

“It’s purgatory, ’cause you can’t do what you want to do as a Black man in America,” he said in early March of these tugs of war about who can steer Black storytelling in fashion, and to where. “You’re working with the confines of what white culture at large wants you to do, and also what Black culture at large expects of you.”

Rather than shy away from the hard conversations, though, Mr. Emory is leaning in. He was speaking at the still-spartan Denim Tears office on West Broadway in Manhattan, around the corner from his first permanent retail space, African Diaspora Goods, which sells his brand alongside a collection of 2,000 African art history books, which will eventually function as a kind of non-lending research library.

Denim Tears is currently best known for the cotton wreath motif that Mr. Emory began applying to vintage Levi’s jeans in 2020 — originally as a limited release that felt more like an artistic than sartorial intervention, and subsequently much more widely on jeans and caps and sweatsuits. The goal was discursive, to highlight the product of slave labor and make it manifest on the product itself. In the last year especially, the wreath has become one of the most recognizable, ubiquitous and now widely bootlegged logos in streetwear.

“That means that discourse spreads,” Mr. Emory said.

Part of Mr. Emory’s influence and power comes from how he brings these reference points into quotidian, easy-to-wear garments like jeans, hoodies and T-shirts. “It’s a beautifully utilitarian approach,” said the fashion designer Andre Walker, a close friend of Mr. Emory’s.

The title of the current Denim Tears collection is Kiss My Grits — what his mother (and many others in the South) used to say as a proxy for “kiss my Black ass.” Black food references thread the collection together across disparate design frameworks. The clothes include abstraction (a silk velour shirt and pants in the colors of the spices used to make fried chicken), pop art (watermelon wallets, green rind on the outside and red, seed-filled meat on the inside, made with Comme des Garçons); and baroque painting (a hoodie with a still life of various fruits). There are shirts done in a picnic-tablecloth pattern and necklaces made of chicken bones sealed in resin.

Mr. Emory’s use of this imagery walks a “beautiful tightrope of subtlety and obviousness,” Mr. Walker said.

These signifiers are drawn directly from Mr. Emory’s upbringing spending summers in rural Harlem, Ga. — the breakfast table at his mother’s home or his grandfather’s truck filled with watermelons (or his father’s stories of getting shot at by white farmers for stealing watermelons).

“That’s who I come from,” he said. “You know what I mean? So I don’t feel shame about no watermelon. It’s a part of my culture,” Mr. Emory said. “The same type of white folk that burnt down Tulsa, they turned that into a racial trope. And I’m not going for that.”

The chicken bones that are made into necklaces? They reference bone-throwing divination rituals, and also refer to how a young Mr. Emory would watch his father crack bones and suck out the marrow. It’s also a nod to Vivienne Westwood and the Let It Rock boutique, which sold clothes with chicken bones attached.

For Mr. Emory, though, the clothes are part of a long pattern of embedding personal narrative into his designs. The dusty red of an Asics collaboration he released in 2021 referred to the clay of Mr. Emory’s family funeral plot in Georgia. One of his earliest T-shirts, which he sold at pop-ups in New York, prominently featured a photo of his mother, who died in 2015. (And Mr. Emory has used Black cuisine as a trope before: The collection he released with Dior in 2022 featured a collard green motif.)

This time around, however, some of the online chatter from Black critics has been unsparing. “Part of why it’s polarizing is because people don’t see me as an artist,” Mr. Emory said. He sees his clothing in a tradition that includes David Hammons’s 1970s artworks that used spades, Kara Walker’s “A Subtlety,” the Sphinx-esque installation at the Domino Sugar Factory in 2014; and Spike Lee’s film “Bamboozled.”

“If people think I’m on some Stepin Fetchit, Black Sambo,” Mr. Emory said, “you’re really not paying attention.”

He added, “I’m making a pawn a king.”

Mr. Emory refers to these online critics as “the loud minority.” “If it was the loud majority, I wouldn’t be sitting here,” he said. “I wouldn’t be able to pay my staff. I wouldn’t be able to open a store. I wouldn’t be able to pay my expensive-ass health insurance.”

He has also been attacked for marrying a white woman. “I’ve been made fun of for dating a Black girl with natural hair, and I’ve lived long enough to be made fun of for marrying a white woman. I’ve seen both sides,” he noted, with a rare flash of exasperation. “James Baldwin dated white men and he’s the most prolific, most quoted Black thinker to ever live.”

Andee Emory McConnell, who Mr. Emory married in October, has watched him navigate the critiques up close. “It’s his soul coming out into the form of the pieces that he chooses to put out into the public,” she said. “And when someone comes for your soul, how can you not take that to heart?”

The Road to Recovery

Much of the conversation about Mr. Emory and his work mirrors the discourse about Mr. Abloh — alternately dragged and praised, sometimes by the same people — in the final years before his death in 2021. Mr. Abloh was the most visible Black designer in men’s fashion, and his success opened up doors for a younger generation, but the persistent and often persnickety meta-narrative about his work was draining. That Mr. Emory is experiencing similar pushback during a period of time where he is still navigating his medical recovery — much as Mr. Abloh was, largely in secret — isn’t lost on him.

He was hospitalized for the aortic dissection eight months into his time at Supreme, a near-death experience that led to two induced comas, a fasciotomy on his left leg, pneumonia, blood sepsis, kidney failure and dialysis — all in the span of just a few weeks.

Mr. Jafa visited him in the hospital. “I said, ‘It’s not your time,’” he said. “You’re supposed to be here. We are not supposed to lose you the way we lost Virgil. You got more that you’re supposed to do.”

When Mr. Emory got home from the hospital, he couldn’t sleep with covers on, because the nerves in his legs were too sensitive. He left the hospital in a wheelchair, eventually graduated to a walker, and now walks slowly and deliberately, aided by a hiking stick. For shoes, he wears only Hokas, apart from the rare night out. Three times a week, in the sleek, minimalist, book-filled TriBeCa loft he and Ms. McConnell share, his physical therapist arrives for a private session.

Not all the hurt is physical, though. Mr. Abloh’s passing left a talent vacuum. “Because certain other people aren’t here,” Mr. Emory said grimly, “the target’s on my back.”

Mr. Emory’s close relationship with Mr. Abloh informed his development as a clothing designer. “V is the first person in my adult life who was like, ‘You’re an artist,’” he recalled. When Mr. Emory first showed him the image of the wreaths, Mr. Abloh said: “This is beautiful. Six months, you gonna have a Maybach.”

Mr. Emory laughed a little. “So I’m making good,” he said. “I didn’t buy the Maybach. I did this store.”

That store opened last month in the old Union space on Spring Street in SoHo, one of the foundational addresses in New York streetwear history. (In a rich coincidence, Mr. Jebbia was a founder of Union.)

The space was wholly redesigned by the artist Theaster Gates in an update of a design he’d first displayed at a 2019 exhibition at Regen Projects in Los Angeles in preparation for collaborating with Mr. Abloh on a possible store.

On the right wall, made of torched plywood over a steel frame, are Denim Tears clothes, hanging face out on lengths of pipe. On the left wall is the African art-book collection, which Mr. Emory bought for $150,000 from Arcana Books in Los Angeles, works its owners collected over four decades.

“A site of Black possibility” Mr. Gates called the shop. “We didn’t have the burden of the whole space being a retail store. It was like, ‘What if people came in and they were a little bit confused about what was happening here?’”

Productive confusion is Mr. Emory’s métier, and both his falling out with Supreme and the recent Denim Tears blowback turn in part on how the Black experience should be captured on clothing, especially clothing that may be bought and worn and displayed out in the world by people who haven’t lived that experience. Or, as one TikToker put it, “Can white people wear Denim Tears?”

For the record, Mr. Emory’s answer is yes: “If I see a little white kid wearing it, I’m like, fire. I wonder what the conversation is up in his crib. Maybe the conversation’s beautiful and the dad’s like, where’d you get that shirt? Can we look it up?” Or perhaps it goes another, equally revealing way: “Maybe the kid gets into an argument and realizes that even though he loves his dad, his dad’s a racist. And maybe the kid’s like, I never want to be like this part of him. Maybe that happened because of that conversation about the T-shirt.”

These are some of Mr. Emory’s crucial questions: Is there a distinction between a gallery and a T-shirt? How vast is the chasm between style and art? Are some images too unsettling to put on clothes? And should images that are so unsettling be looked at even more intently?

A Desire for Discourse About the Past and Present

“I think the reality is that Tremaine craves discourse,” said Anthony Specter, Mr. Emory’s close friend of more than a decade and business partner in Denim Tears. “Tremaine’s exit from Supreme, a lot of that revolved around the fact that there was no discourse. It wasn’t about someone attacking his idea. The most stressful part for him, the part that made him realize he couldn’t do his job, was that he wasn’t able to talk about it.”

Mr. Emory received the Supreme offer the week of Mr. Abloh’s death and began the job in February 2022. Mr. Abloh, he said, had warned him not to take it: “He said: ‘What would it take for you to culturally move that brand? Do you really want to extend that energy?’ And boy was my brother right.”

Mr. Emory had long been in the social orbit of Supreme, a now-big company — acquired by VF Corporation in 2020 for more than $2 billion — that still functions like a private party. His tenure there lasted only about 13 months, not counting the five and a half months he was on medical leave.

Despite having hired Mr. Emory as creative director — the first time the insular company had hired someone with that title — Mr. Jebbia remained a hovering presence, Mr. Emory said. Not long before Mr. Emory’s hospitalization, he and Mr. Jebbia had a face-off in a meeting over control.

“I had to really put my foot down with James,” Mr. Emory recalled. “I said, ‘Are we Miuccia and Raf? Because I wasn’t hired under that pretext. I was hired as you were stepping back.’” (Miuccia Prada hired Raf Simons as a co-creative director of Prada in 2020.)

Through a representative, Supreme declined to comment.

In creative meetings, Mr. Emory would sometimes be told a project he suggested, or had done at Denim Tears, was admirable but couldn’t work at Supreme. But Supreme has deployed the patina of Black radicalism previously, whether images of Martin Luther King Jr. or a Black hand extending a middle finger on T-shirts in collaboration with the hip-hop duo Dead Prez. It has featured umpteen rappers on shirts and played with imagery far less radical, like the presidential headshot of Barack Obama. It has also showcased provocative art, like Andres Serrano’s “Piss Christ.”

But Mr. Emory found those engagements to be surface level: If the staff was unable to truly talk about the complexities of Black life and culture, then “why are you touching it at all?” he wondered.

Mr. Emory realized he hadn’t been brought in as a change agent. He recalled a meeting about whether to release a shirt featuring the controversial young rap superstar YoungBoy Never Broke Again, in which concerns about his criminal history were being weighed against his popularity on streaming services and among young people. The project was approved.

Mr. Emory recalls Mr. Jafa saying, “Does James listen to NBA YoungBoy?” Mr. Emory continued: “He wasn’t trolling James. What he was saying is, ‘If you listen to it, the lyrics are dark. The darkness isn’t far removed from how dark my work is.’ That’s what AJ was saying. Like, do they not see if you could do NBA YoungBoy, you can do me?”

Mr. Jafa had been one of Mr. Emory’s first calls when he arrived at Supreme. When Mr. Emory was still working for Mr. West, he’d brokered a meeting with Mr. Jafa, who’d used Mr. West’s music in his breakout 2016 video work “Love Is the Message, The Message Is Death”

For Supreme, they planned to collaborate on items using some of Mr. Jafa’s rawest imagery: including “LeRage,” featuring a Hulk-esque character depicted with hyperbolized cartoon art to underscore Black frustration; and “Ex-Slave Gordon,” an image of a free Black man showing the scars from whippings he’d suffered while in bondage.

“People always think if you are a Black visual artist, that your stuff is supposed to be in some ways relatable or palatable — I call it after-school special,” Mr. Jafa said. “I do what I want to do. I’m not interested in white folks telling me what to do. But neither am I interested in Black people telling me what to do.”

The clothing went through the usual channels for collaborations. Samples were produced. And then, silence. After a junior-level Black employee complained to Mr. Jebbia about the imagery, saying it belonged in a museum, not a skate shop, the collaboration was effectively shelved. No one spoke with Mr. Emory about the collaboration’s fate.

During a meeting discussing the work of the Black artist Lauren Halsey, Mr. Emory said he didn’t want to discuss working with Black artists until getting clarity about the Jafa collaboration. Soon after, he received a call from human resources, he said, saying they’d received a complaint that the meeting had been “emotional and racially charged.”

After his resignation, Mr. Emory and Mr. Jebbia had a frank and vulnerable four-hour conversation at Mr. Emory’s home. Mr. Emory said that Mr. Jebbia said that the reason he never talked to him about the Jafa collaboration, was “cause he knew I would change his mind.” At one point, Mr. Emory said, Mr. Jebbia had tears in his eyes.

“I’ll always respect him because he did things wrong in my opinion, but he looked me in my eyes and talked to me like a grown adult,” Mr. Emory said. “He apologized to my face. And he’s the only person in the company that did that.”

But after the Business of Fashion published an account of Mr. Emory’s exit framed in a way he found disingenuous, “I texted James just a picture of the ‘White Fragility’ book. I said, ‘I hope one day you read this book so you can really understand where I’m coming from. I don’t know if me and you will ever speak again. But regardless if we do, I hope you read this book.’” (Ms. McConnell, who had worked at Supreme as well, quit after that article’s release.)

In that same conversation, Mr. Emory said Mr. Jebbia expressed hope that Mr. Emory would consider returning to the position, but Mr. Emory declined.

“People, in interfacing with Tremaine, treat him with love and excitement and exuberance,” Ms. McConnell said. “And I think that maybe he’s learned, which could also probably be a little heartbreaking, that sometimes there’s things under that he needs to pay attention to.”

Mr. Emory concurred. “You’re hiring a guy that does Black Jesus with the cotton wreath on his head as your creative director. I felt like, ‘You’re a real one,’” he said. “And to have it go down like this, it makes me feel like I was wrong.”

Asked whether he’d consider taking a creative director role at another white-owned fashion brand, Mr. Emory wrestled with the question in both micro and macro form.

“If the people didn’t value Virgil being at Louis more than Off-White, maybe he wouldn’t have took the job,” he said.

“Hubris is a hell of a drug,” he continued. “I can be honest and say I work steadfastly on my validation index and focus on only finding validation from seeing a kid of any color wearing DT in the streets. But I don’t know. I don’t want to cap you down, man. I don’t know.”

For now, the freedom of Denim Tears is what soothes and sates Mr. Emory, whether it’s his ability to release the Jafa collaboration with no pushback — “Are we supposed to hide these scars and never look at these scars again?” — or his coming collection themed around Black jockeys, whose hidden history Mr. Emory’s father taught him about.

“Some people don’t give me grace that maybe I’m thinking hard,” he said, more resigned and frustrated than angry.

Ultimately, Mr. Emory and his critics agree that no version of the Black experience is universal. “My view is I can’t tell another Black person how to feel about their Black experience, because Black people aren’t a monolith,” he said, acknowledging that the uncomfortable discourse is, in many ways, key to his creative project.

“They have the right to unfollow me. They have the right to leave a comment. They have a right to not buy it, tell other people not to buy it. But what they can’t do is change what I’m gonna do.”