"He Was the Ultimate Creative Director": The Oral History of Sean John, Diddy's Game-Changing Clothing Label

It's nearly impossible to find pictures of Diddy not surrounded by celebrities—often ones he's hand-selected. Similarly, it's hard to imagine him away from his sold-out arena shows, or not dressed head-to-toe in white for what were long the hottest parties in the known universe. "He's been in a very high octane world of celebrities. He's been in the world of music, he's been in the world of Vogue, he's been in the world of movies and the world of fashion," says Vogue editor-at-large André Leon Talley. But Diddy's accomplishments were the result of hours spent in small dark rooms. Chart-topping songs produced to perfection in low-ceilinged studios. A record label forged after hours at his day job at Uptown Records. And, birthed in a secret record label cubicle, Diddy's multi-million dollar apparel brand: Sean John.

That Sean John was born under a cloak of secrecy is surprising considering that in 1997 Diddy was rocketing to the top of the world. Then known as Puff Daddy, he'd just released his debut single "Can't Hold Me Down," which spent more than half of the year on the charts, and his debut album No Way Out had been a chart-topper for 11 straight weeks.

But away from the spotlight, that same year, Sean John's long-serving president Jeffrey Tweedy was given a tight cubicle in the offices of Diddy's record company. Diddy wasn't supposed to be launching a new brand there—so Tweedy told everyone, per Diddy's marching orders, that he was there working on "tour product."

Sean John wasn't operating in a vacuum, though. To this day, Diddy and Tweedy recall just about every brand making what used to be called "urbanwear": Tweedy remembers it as 36 other brands, while Diddy's hitlist clocks in at 30. When Sean John officially launched in 1998, it would sit next to the likes of Fubu, Phat Farm, Rocawear, Cross Colours, Karl Kani, and Akademiks. In 2018, the number left standing hovers in the low single digits. "I was and still am focused on creating a lifestyle brand with Sean John," Diddy says. "I believe if you stay true to your vision and make great products, the rest will take care of itself."

Sean John is now a globally recognized brand, a winner of fashion's highest award, a mainstay in every Macy's in America, and a $525 million-in-annual-sales behemoth. Sean John was the first brand to ever have its runway show simulcast nationally, on E! and its now-shuttered Style network. 20 years ago, Sean John launched at Bloomingdale's, a coming-out party for a revolutionary brand. "I remember it being tremendously exciting," says Stephanie Solomon, who worked at Bloomingdale's at the time alongside the department store's late influential fashion director Kal Ruttenstein. "You felt you were on the verge of a new breakthrough in fashion." This is the story of that breakthrough.

Building a Brand

Jeffrey Tweedy would start at the offices early, 8:30 a.m or so, because, he explains, "A record company doesn't start until 1 p.m." Diddy would bring musicians like Jay-Z, Busta Rhymes, and Mase around, and hours after Tweedy had gone home for the day, they'd sneak a look at the "tour product." And rubberneckers didn't leave empty handed. An order of 30 hats would disappear overnight; Tweedy would complain that his work became party favors for Diddy's friends. "He says, 'What's wrong?'" Tweedy recalls. "I say, 'I leave, everything is gone. I'll have out 30 hats and there's eight left." He goes, 'Well'—he's very smart—'whatever was left, make sure we don't buy that because no one wanted it.' That means the color was wrong and no one wanted it. So even then he understood marketing and design product." Tweedy found a locker to hide his samples, but those early moments crystallized who he was designing for: the massive celebrities Diddy rolled with, and the fans who aspired to be like them. "There were a lot of late nights," Diddy says, "but we all knew how important it was to get it right." And with friends like Tommy Hilfiger and Anna Wintour, he was well on his way.

Jeffrey Tweedy (Sean John president): I got several calls from [Diddy] about starting a brand. I didn't take his call for awhile because I was like, "Bad Boy Jeans? What are we doing?" He had a three-year plan already laid out, from what the collection looks like to what we do with it to where we market it how we market it to who we put it on. He had done his homework.

Tommy Hilfiger (designer): My brother Andy brought Puff Daddy into my office. I loved his confidence. I loved the way he looked—he was decked out in some Tommy. There was no doubt in my mind this guy was going to be a true superstar and contender in whatever he chose to do. He told me he wanted to conquer fashion as he had already started to do with music.

He actually wanted to partner with me. My partners only wanted to focus on Tommy Hilfiger at the time.

Diddy: I truly appreciated [Hilfiger's and Anna Wintour's] friendship and support and the way they welcomed me into the fashion industry. I listened to everything they had to say, and in the end what I took away from their advice was to rely on my instinct.

Tweedy: The first thing he said was, "I don't want big logos. I want small. I want the best velour. I want the best jeans." His vision was really, "I want to do an incredible sportswear line that hasn't been seen out there, that's aspirational. It's not Ralph and it's not Donna Karan. It's my lifestyle. Puff's lifestyle."

Christian Combs (model, musician, Diddy's son): The brand was actually named Christian Casey LLC when it first started. And the day I was born was the day my dad first had his Sean John hats, so he was giving them out to everybody. I feel like me and the brand are just automatically connected forever.

Tweedy: I would go to the store when collections first launched and there were so many people who would walk by, like, "I'm not wearing Puff Daddy's clothes, I don't like him." Then all of a sudden it turned into, "This is hot."

Diddy: Jeff [Tweedy] initially faced some pushback from the retailers who categorized us as urban and as a celebrity without staying power, but that wasn't something I ever thought about.

Solomon: [The night of the Sean John launch party,] it was a madhouse in Bloomingdale's.

Diddy: I was greeted by Kal Ruttenstein, a true legend in the fashion industry, and he was wearing Sean John himself. There were cameras and press everywhere and we actually shut down the men's floor that night.

André Leon Talley (Vogue's editor-at-large): The atmosphere was electric and the scene was just totally energized by Sean. The bar starts with him—he creates the mood, he creates the energy, the dynamic.

Diddy: Afterwards we moved over to Mr. Chow's for dinner with Anna and André from Vogue so we knew we were making history.

Talley: I wouldn't have gone to Mr. Chow's. That would have been exhausting by the end of the evening. I would have been going home. My favorite place is to be is at home.

Diddy: I went back to Bloomingdale's after my first runway presentation to kick off the season and they gave Sean John the entire stretch of windows on Lexington, which I believe is the first time they did so for any brand. We shut down the avenue.

The First Fashion Show Fit for TV

Diddy ran a celebrity-driven label before anyone really knew what that meant. He turned his fashion shows into must-watch television. He appeared on the then-happening TRL—often in his own clothes—a record 39 times. And he used the paparazzi and tabloids' unquenchable curiosity to his advantage. "People were obsessed in terms of what was his name, and who was he dating, and where was the party, and what did he wear at the party? Where'd they go, and what did they eat?" says Estée Lauder's executive group president John Demsey, who worked with Diddy on his Unforgivable fragrance. "All those young guys out there wanted to be him. It wasn't just the urban customer, it was the white kid in the suburbs dreaming about this glamorous life."

"This is Puff's J-Lo era," says Dao-Yi Chow, former Sean John creative director and now half of the brand Public School, "so it was just like a magnifying glass was on everything, and everything he did, and that extended to what we were doing at Sean John." Diddy and Sean John welcomed the spotlight: in 2001, E!, in conjunction with the now-shuttered Style network, breathlessly announced in a press release it was set to "simulcast the first-ever live fashion show" from Bryant Park, where New York Fashion Week shows took place at the time.

And for its 17-minute run, the Sean John fashion show was the center of the universe. 1,200 people in total attended and the show is a time capsule of 2001 celebrity: attendees included Paris and Nicky Hilton in matching beaded sequin dresses, Christopher Meloni of Law & Order fame, Faith Evans, the members of 3LW, Kevin Garnett, Luther Vandross, Stephen Baldwin, Collective Soul, a pre-Modern Family Sofia Vergara, and O.J. Simpson's defense attorney Johnnie Cochran. The E! special included over an hour lead-up and the program went back and forth between celebrities showing up and Diddy backstage prepping for the show. When the clothes finally emerged, the crowd was in a lather. Diddy, hailed as a master marketer and promoter, had made anything else printed with Sean John's cursive-script logo the most desirable items in the world.

Diddy: We were making history. No other show had the kind of excitement that we were putting out there. The added pressure of being broadcasted live and having so many of my friends there only made me elevate my game. Anna [Wintour] told me that we brought back the excitement to fashion week.

Tweedy: Keep in mind: Marc Jacobs was doing a show. Calvin [Klein] was doing a show. Donna Karan was doing a show. Ralph [Lauren], Tommy, everybody was doing shows in New York City. And [E!] say, "We want to follow one. We're doing Sean John."

Fonzworth Bentley (Sean Combs' former personal valet): Hip-hop at its core is still, What do you do the best? Either you're like, "I'm the best lyricist" or "I have the most panache and swag when I talk my talk" or "I pick the best beats." And so that approach was what Sean Combs brought to fashion. It was like, Look, if we're going to do a fashion show, it's going to be the best.

Chow: Back then, no one would want to sit through a men's show. We were doing shit that [Louis] Vuitton, and Dior, and [John] Galliano, and all these houses that had been around for decades were doing.

Tweedy: It was really taking Puff being on stage and saying, "How do I do what I do in an arena in front of 40,000 people and put it on this narrow, 60-foot runway with the lights and the bells and the whistles and make it exciting?"

Michael Williams (co-founder of the PR agency Paul + Williams, who worked on Sean John in the early aughts): These fashion shows were huge and we would get like an onslaught of people trying to get in not just leading up to it but also at the door. It was like a nightclub.

John Demsey (Estée Lauder's executive group president): You felt like if you weren't invited to his show, or you weren't invited to his dinner, you were sort of not happening.

Talley: I remember very much being happy to be backstage and the excitement. The casting was unique, there was so much diversity in the casting. And it was jam packed, it was all sorts of high-tech equipment. It was crowded in the back, it was hot, it was dark, it was exciting. One felt that they were part of something very special.

Tweedy: We would be backstage at these shows nervous as hell.

Talley: I may have just been in the back giving support. He didn't need a stylist. Never!

Demsey: Mary J. Blige and Faith Evans and Little Kim, Iman, and the list would just go on, and on, and on, and on. Everybody was there. I mean everybody.

Diddy (in a voiceover before the show): See, everybody always asked me why I started designing clothes. I basically just wanted to look good, man. You know, to be perfectly honest, I was just, like, looking at myself and saying, "Boy, Goddamn, you look good!"... I just wanted to walk down the street like I was Shaft or John Travolta. I just wanted to feel what it would feel like to one of those superbad, superfly motherfuckers!

Talley: What stood out to me was the fabulous clothing. Even I ordered two coats, I think. There were two big parkas, like you'd wear if you were in an Alaskan outpost or something, with some big fur collars.

Naomi Campbell (supermodel): When the men came out in their fur coats, it took New York by storm. It was amazing. The men were so chic! It was absolutely brilliant. It was back in the day when fashion shows were truly entertainment and everything about the show was captivatingly beautiful and just fun! He spared no expense, and he wanted it to be the best. And so it was.

Christian: I remember mad cameras flashing on me and my mom and my brother. I just remember the hype that was around it.

Life at Sean John

A brand that started with Tweedy and a couple freelance designers working out of a record company's office evolved in just six short months after the Magic tradeshow, where the brand first attracted stores, to 12 people in a New York City design studio. Diddy knew how to amass talent. When Christopher Bevans, who now runs the brand Dyne, worked at Sean John in the early aughts, he overlapped with Todd Hoover, who now runs Abercrombie & Fitch's technical department; Gemo Wong, now head of special projects at Nike; and Dao-Yi Chow and Maxwell Osborne, who would go on to launch the brand Public School. ("Max, of course, was our intern running around the office," Bevans says.)

The brand sprouted new arms, like a premium denim line. Sean John became a darling of the fashion industry and was nominated for its most prestigious award, a CFDA (often called "the Oscars of fashion"), four years running before finally taking the trophy home in 2004 when he beat out Michael Kors and Ralph Lauren. Critical success led to massive commercial success, and the brand found a dedicated pack of customers at one of the country's biggest retailers. In 2010, Sean John struck a deal with Macy's that gave the retailer its sportswear collection exclusively, and brought Diddy's brand to every nook and cranny in America, cementing Sean John's status as an iconic brand.

Chow: Coming to work every day, you had no idea what to expect. One day he likes the collection. Then the next day, he's like, "I hate it," and we'd design another line. You never knew what the fuck you were gonna get.

Bevans: Puff would walk the hallways and just see our work and he was just so much fun. And the music that was going on and the energy that Puff brought, the freedom that he would give us with our designs and it was just really special.

Chow: Everybody came through. There was not an artist that didn't come through, from Black Rob to Mase. It wasn't even just his artists. I remember going to fit Will Smith for Oscars one year, and then fitting Chris Rock for a tux. Puff always made sure that all the artists got clothes.

Williams: I'm not blowing smoke up anyone's ass, but [Diddy's] brain is going so fast and he's so far ahead of everything and everyone that, to me, it sounded like he would be frustrated because he would want stuff to really happen and he had a lot of ideas.

Chow: He couldn't take no for an answer. If he wanted to get something done, it had to get done. That's what made those shows so iconic. He knew exactly what he wanted, from the music, to the styling. He knew he was the ultimate creative director.

Fonzworth: In '01, we were in Miami, and he recognized that I didn't wear any Sean John. And I remember within a week he flew his entire Sean John design team to Miami and was like, "Hey, this is Fonzworth, and he's a fashionable guy and he doesn't own a stitch of Sean John clothing. You need to find out why and you need to fix it." Then he just walked off.

Chow: His clock was working on music industry standards. So come to the office at one, but stay there until three in the morning. Then you'd have to go out. When he was up, he expected you to be up. If he was in Miami, he expected you to go to Miami or Saint Tropez for three weeks. Whatever it was you would have to go. Working on a yacht and then you're at break at day. The line between work and play was blurred.

Diddy: My life takes me all over the globe and I am doing business no matter where I am. In creating a fashion line like Sean John, there are deadlines. So if I am in St. Tropez or Paris or London, my team will have to come to me so we can make the deadlines and create an amazing collection.

Williams: Puff would always be doing stuff like shooting a video or going to the Super Bowl. And it would seriously be Friday at 4 o'clock and someone would come up to me like, "Puff's doing a video—we need this whole collection carted and sent to Miami." And I'm like, "Dude, every piece is at a thousand magazines, there's no way this is happening. And they'd be like, "IT NEEDS TO HAPPEN, PUFF WANTS THIS. GET IT DONE!"

Chow: [Diddy] used to burn the scent Baies from Diptyque.

Diddy: Actually, the scent was Tuberose.

Chow: That was the scent that he burned at his apartment. So he wanted all of Cipriani [the location for Sean John's 2002 fashion show] to smell like [Tuberose] from Diptyque. I remember the night before, he sent out [everyone], no matter who you were, if you were designer, if you were the creative director, if you were the marketing person, if you were an intern. We bought up all the Dyptique candles in New York City. And that was still not enough. We had to get the actual spray scent.

Diddy: I am an entertainer and I wanted to create an experience for everyone who came to the show. Part of that experience is sensual and the sense of smell is closely connected to memory. I wanted this scent to hit everyone when they first walked in the door and I knew they would never forget it.

Fonzworth: I remember before Cipriani, Puff was like, "You're going to walk in one of the looks" and he was like, "You're gonna come around that corner and you're gonna be shook." I'm like, "Bro, you gotta be kidding me! I've been waiting my whole life this moment." But I remember coming around the corner and as soon as I stepped out there I probably threw up in my mouth a little. There were so many people and... they were all there. I'm talking about fashion editors and writers. I was like, wow, [Diddy's] this kid from Harlem, who went to Howard University, an HBCU, and this culture was just magnetized to him.

Christian Monzon (Sean John model): Channing [Tatum, who was a model in Sean John's 2003 runway show,] is standing behind me, we're lined up, He taps me on the shoulder and goes, “Yo, C, we're next.” I'm like, “What do you mean, the music hasn't even started?” He's like, “No, man, we're next! Look what we're doing, Diddy just came and fixed your coat." I don’t know what [Channing] was doing at the time, but think of that mindset that was set up at that moment for him. That's how powerful Diddy is.

In 2004, Diddy became the first African-American designer to win the CFDA Award for menswear.

Fonzworth: The thought process was: we may or may not win, but we finna kill 'em on this red carpet and we about to be the best-dressed folks representing any fashion house up in this thang.

Chow: When [Diddy] won the CFDA award in '04, that was a huge, huge, moment historically, culturally. This was back when the awards were still at the New York Public Library. He had a white tux on. Black pants. I think we knew that year, that we were gonna win it. We just had a feeling. It was long overdue.

Diddy: I had been nominated for several years prior to winning and I kept going back because I knew we deserved the recognition. To be the first black man to win this honor meant so much to me and the community I represent. The award solidified Sean John as a true fashion brand and not a fly-by-night celebrity-endorsed brand.

Fonzworth: It was a Jackie Robinson moment. This was the first time an African-American had won, so I just remember this was really the culmination of all the work that had been done and it was finally acknowledged by the highest level in the industry.

Christian Combs: He [told me he won] in such a swaggy way. He told me after I went to the CFDA awards. I'm like, "Yo, I didn't even know what that was." I just saw a bunch of statues and he was like, "You know I won that?" I was like, "Word?" He was trying to flex on me a little bit with that.

Bevans: It inspired me—just being a young, black male in the industry and working for somebody that I really related to.

Chow: The next black designer to win Menswear Designer of the Year is [the other half of Public School] Maxwell. There's a legacy there.

The Sean John Ripple Effect

Back in 1999, Forbes started its Celebrity 100 issue to showcase the top-earning celebrities. On its cover was none other than Sean Combs, not in a "snappy suit," as Forbes writes, but in a Sean John T-shirt. In 2017, he held the number one spot on the celebrity hot list. It speaks to the longevity of his brand—but also to the effect it's had on culture as a whole.

Sean John was a cultural force, and that was mostly by Diddy's design. He wielded the power at his disposal to effect change in the industry by hiring and putting on designers of colors. He required that a majority of the models cast in his shows were of color (14 out of the 25 models at the iconic 2001 fall fashion show were either black or Hispanic). Before it was sold exclusively at Macy's, Sean John was a legitimate trendsetter, and not just for its clothes. Which streetwear brand took on huge investment money before Supreme? Sean John. Who was the performer-turned-designer creating a legitimate fashion business before anyone had heard the name Kanye West? Diddy. Which brand was fusing streetwear and fashion when executives still stuck up their noses at the idea? Sean John.

Sean John also made clothes that are still mainstays in people's closets. The velour tracksuit, the item that made Tommy Hilfiger certain that Sean John would be a success, all the way back in 1998, was worn by Rihanna almost 20 years later. And the now-ubiquitous streetwear-meets-fashion trend dominates what sells at major retailers in 2018.

Steve Stoute (the author of The Tanning of America: How Hip-Hop Created a Culture That Rewrote the Rules of The New Economy, who helped created the marketing campaign around Diddy's fragrance): The designers before him, urban designers before him—Karl Kani, FUBU and Cross Colors—that stuff existed, but what he did, which made it revolutionize fashion, was [take] it from being urbanwear to being positioned as a designer. It's almost like if you look Black Panther today. It's like, "Oh wow, you can have a black man worth $200 million, you can have a whole black brand."

Chow: I remember we were [in the apparel section labeled] 'young men.' Then it became 'urban'—that was the catchphrase. It was only urban because the designers were black. We were doing the same product as Ralph, and Tommy, and Calvin.

Fonzworth: I remember telling him he needed to focus more on the brand less on music and he was like, "What!?" I said, "I'm telling you, you have a real opportunity here." Thinking about the landscape of the brand and a lot of brands that had come from urban culture—some of them were losing steam.

And I remember him coming out of that next [finance meeting], the following year after that ['02] fashion show, and he's just like, "Yo, motherfucker, you right. I ain't never seen no numbers like this."

Stoute: [Sean John] gave an entire generation the confidence that it could be done. If you look at Kanye and Jay-Z and Fear of God and all these guys who are now legitimate designers, they would not have had that opportunity if it wasn't for the path that Sean John laid.

Tweedy: [At model castings, Diddy would shout,] "I want more black guys!" We did one show of all black models. We got ridiculed for it in the press. The next season, all over New York and Paris, everybody used all black models.

Chow: People throw around the word "disrupter." Nowadays, I think he was the original disrupter from a fashion and industry standpoint.

Fonzworth: The really key point is that he really began to change the culture. At that time, people were wearing white T-shirts and Mitchell and Ness and oversized jeans. This really began a transition in hip-hop, which ultimately electrified menswear.

Talley: Fashion certainly did embrace him and wanted to have this star, this big hero. He became a hero.

Christian: [Rapper] Desiigner was like, "I was trying to get draped in Sean John for fashion week." I told him I would be his stylist.

Diddy: I got a message from Kanye West the other day: "Look, you're all over my mood board!"

Diddy: Being an inspiration to others means that we are doing something right. It is and will be the legacy of the Sean John brand.

Solomon: It was so influential that if you look on the streets today, all you see are remnants of Sean John's first collection. The oversized, puffy jackets. The dress pants. The sneakers… It changed the way men dressed

Bevans: The obvious X-factor is just the brilliance of Puff.

Hilfiger: Never underestimate PD.

Fashion Editor: Kelly McCabe. Assistant: Miles Pope. Grooming: Barry White.