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Jaden Smith on Defying Gender Norms, the ‘Fresh Prince of Bel-Air’ Scene That Inspired His MSFTSrep Collection & Fashion’s Sustainable Future

By Stephen Garner,


Jaden Smith knows how to make an entrance.

On a January afternoon in Los Angeles, the 24-year-old is camera ready when he arrives at PMC Studios in a purple cropped jacket from his own brand — sans shirt underneath — and hip-hugging Supreme cargo jeans with Calvin Klein underwear peeking out.

The musician and designer — who styled himself for this month’s FN cover shoot — clearly understands the assignment as he moves quickly and decisively through the racks of clothes, shoes and jewelry, all from Black designed brands in honor of Black History Month.

Jaden immediately loves a veil hat from Romeo Hunte, which he wears for the first look with a textured Off-White suit, a pair of Telfar logo boots and a Wu-Tang ring by Brooklyn jewelry designer Johnny Nelson. He also gravitates to a pair of Ugg x Shayne Oliver boots, lighting up when he sees the work of one of his favorite design talents. “I really loved what Shayne did at Hood by Air a few years ago, and I’m so glad the label is making a comeback,” Jaden said.

The son of much-buzzed-about Hollywood power couple Will Smith and Jada Pinkett-Smith, Jaden has been an astute observer of fashion ever since he launched his own brand at the age of 14 – a year before he moved out of the family home in a bold show of independence.

“I took the time to see multiple perspectives of the world and decided what was best for me and how I wanted to make an impact,” said the self-described activist, who burst onto the Hollywood scene in 2006 when he starred alongside Will in “The Pursuit of Happyness” at age 8.

While acting was a natural first step, the artist has immersed himself in a variety of mediums. He’s been active musically for more than a decade — and followed up his 2010 appearance on Justin Bieber’s “Never Say Never” with his debut mixtape and later three full-length albums.

The multi-hyphenate creative also operates a sustainable water business (he requests that no plastic be brought on set) and a vegan food truck that feeds people healthy meals on Skid Row. “I want to [make everyone aware] of important issues around us that we may ignore,” he explained.

As he builds his platforms in new ways, Jaden is keenly aware that no matter what he does, some people’s preconceived notions about him won’t change, as he and his sister Willow have faced endless scrutiny from Hollywood elite for years now, sometimes being branded as “odd” or “outrageous.”

Nevertheless, Jaden’s style choices, which often defy gender norms, have become part of his persona. He’s frequently spotted in skirts, cropped blazers and painted nails. He often pairs his looks with New Balance sneakers and has collaborated with the brand on several styles.

But for Jaden, it all comes down to one thing — being his authentic self. “It doesn’t matter how I dress,” he said. “People are always going to perceive me whichever way they want. I’ve accepted this, which frees me up to be myself. I can’t change anybody’s mind about me by what I wear.”


Jaden began his fashion journey over a decade ago when he co-founded MSFTSrep with Willow, and another sibling pair — actors Moises and Mateo (aka “¿Téo?”) Arias. The label was started as a collective where fellow “misfits” could share ideas.

“I really wasn’t thinking about the fashion industry at all. I was thinking about information in the world and how to best share that with groups of people. I decided creating a movement was the easiest thing to do,” Jaden recalled. “But then it became very clear that people wanted to represent the ideas [through] clothes.”

A decade later, the ethos of the company is still the same — to give people a creative outlet to express their true selves. “My brand caters to people who feel ‘different’ and ‘weird’ or that they don’t fit in,” Jaden said. “There’s a pain that you feel when you can’t express yourself, so this is for those people who just want to be able to do that.”

Jaden’s unwavering vision has helped him carve out a distinct niche in an industry that can often lack originality and purpose, which has led MSFTSrep to be stocked in retailers like Saks Fifth Avenue, Selfridges, LuisaViaRoma, The Webster and Holt Renfrew, among other major retailers, with Europe being a key focus for the brand.

Jaden takes a cerebral approach to design, citing textbooks as a main source of inspiration. “Science and physics really get me going, as well as ancient history and topics that people don’t really know a lot about,” he said.

The latest drop, out this month, explores themes of peace, love and the counterculture of the 1960s. The collection, called “Trippy Summer,” a theme Jaden has explored before, features bright psychedelic colors, twisted fonts and nods to nature, the latter most obviously seen through his sunflower hat.

“I wanted to make people into plants and turn people into flowers,” Smith said. “Because being one with nature is like reaching the highest level of consciousness.”

While thinking of the best way to achieve this in his designs, Jaden referenced a 1993 episode of “The Fresh Prince of Bel-Air,” in which his father dresses up in a sunflower hat and sings with a group of young students in exchange for a passing grade in music — the only way he will graduate from high school.

“It was super embarrassing for his character in the episode, but I thought it was an amazing idea of how to turn someone into a flower,” the younger Smith said. And while he doesn’t re-create his father’s full look, the new hats serve as a crowning statement piece that complements the rest of the collection.

While he doesn’t talk about his family much on set, it’s evident that Jaden’s design philosophy is subliminally inspired by his father. The playfulness he seeks to communicate through his looks mirrors the fun and energetic vibe of the iconic 1990s sitcom that catapulted Will to global fame.


When the “nepo baby” fervor reached a fever pitch back in December, Jaden and Willow Smith were characters in the viral conversation, along with dozens of other celebrities who have followed in their influential parents’ footsteps.

Jamie Lee Curtis, Kate Hudson and others have since sounded off on the controversial label. But Jaden — who repeatedly said during FN’s interview that he doesn’t care what other people think about him — isn’t going to engage on the nepotism topic. “I’m not here to say that something is messed up or cool to talk about,” he said.

Unlike many of his peers, he chose to escape the family bubble at an early age as the first step in charting his own path. “I separated myself from everything that I’d known at the time and caught a different vibe,” he said. “I needed that time to really have those solo thoughts and to think about stuff. It was a big part of me being who I am today.”

Jaden’s teenage years also marked a defining moment in his style transformation, when he began to explore fluidity — long before genderless fashion was apart of the mainstream fashion conversation. His statement-making style is often a highlight for street style photographers, particularly during Paris Fashion Week.

“I arrived at this thinking very early on, and it was great. And I love it. And I’m still here,” he said, emphasizing that it’s ultimately about personal expression.

“While more guys are starting to wear things that are traditionally looked at as things that girls would wear, girls have long worn things that guys traditionally would wear. A girl wearing a hoodie and some Dickies and skate shoes — that’s awesome. People should dress how they want to dress.”


Just like his style choices, Jaden is never one to shy away from causes he believes in. A committed activist, he has created distinct businesses centered around giving back.

One of his projects includes the “I Love You” pop-up food truck, which feeds free healthy vegan meals to unhoused individuals living on Skid Row in downtown Los Angeles.

“COVID prevented us from operating for a time, but I am happy that I was able to bring it back in 2022,” he said.

In December, the food truck returned to Skid Row, and distributed 200 meals. Jaden is looking to pop-up again in the area as soon as possible.

“I see what’s happening in the community and it makes me sad. The more people go down there, the more they are aware of it,” he said. “I want the city and the mayor involved. I just want to make a big impact. When I go down there and start to see smiles on people’s faces and talk to them, it makes me feel good.”

But before Jaden launched his food truck concept, he started his own bottled water company called Just Water as part of an effort to fight plastic polluting.

The certified B Corp. serves up spring water in an aluminum bottle — eliminating the use of plastic. Throughout the year, the company supports organizations that often focus on providing clean drinking water to underserved communities. Some previous partners include Freedom Skatepark, Operation Good, Ebony Beach Club and Ryan’s Recycling.


“We demand a more progressive future.”

Jaden tweeted this powerful call to action last October, on the same day he walked out of Kanye West’s controversial show at Paris Fashion Week, where the Yeezy founder and several models sported “White Lives Matter” T-shirts. It was a stunning moment that marked the beginning of West’s very public spiral , and the small crowd of fashion insiders in the room had a choice to make: Stay silent or speak up.

Jaden didn’t just speak up; he walked out. “I don’t care who it is, if I don’t feel the message, I’m out,” the 24-year-old wrote in another tweet. “Black Lives Matter.”

In a subsequent statement, he wrote, “True leaders lead.”

While Jaden declined to comment further on the situation, it’s clear that he will put himself out there when it matters. “It’s important to stand up for things that you believe in,” he said.

Jaden has been a vocal supporter of the Black Lives Matter movement . In 2020, he joined his mother and sister at a rally for Breonna Taylor and performed his song “Boys and Girls” in front of a screen that showed powerful images from past Civil Rights marches and Black Lives Matter protests on “Jimmy Kimmel Live.”

And since that critical turning point in the summer of 2020, both Hollywood and fashion have continued to push diversity to the top of their agendas. “We’re going in the right direction. But there’s still a lot more work to do,” Jaden said.

Another pressing issue that both industries are tackling, to varying degrees of success, is sustainability, something Jaden has put at the forefront of all his business ventures.

He is proud of the fact that he has turned MSFTSrep into a cruelty-free brand. He moved production to Italy in 2021, uses eco-friendly materials like apple leather, is producing in fewer quantities and makes sure he pays fair wages to factory workers. It’s something he thinks the industry can — and must — do at scale.

“Being able to innovate with a limited number of materials is what makes a good designer,” he said. “I’ve seen it for myself with just even my small brand. And what we’ve been able to do is 100% doable on the highest level. There are a lot of groups of young people who won’t continue to buy clothes that don’t have some element of sustainability. It’s what’s best for the future of humanity.”

Photographer: Blair Caldwell

Style Director: Shannon Adducci

Set Design: Skye Whitley-Guzmán

Grooming: Pam Farmer

Barber: James Gilbert

Fashion Assistant: Emilia Fishburn

Editorial Assistant: Tara Larson

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