By Jean E. Palmieri
with contributions from Marcy Medina
 on February 8, 2018
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While his name may have changed more times than some people change cars, there has been at least one constant for Sean Combs over the past 20 years: The Sean John brand.

The label’s founder, born Sean John Combs, has been known as Puffy, Puff Daddy, P. Diddy, Diddy and now, Love. But for the hip-hop entrepreneur, they’re all just names that reflect different periods in his life. Call him what you will — his success speaks for itself.

His earnings in 2017 alone, according to Forbes, were $130 million and his net worth is estimated at $820 million, edging out even Jay Z, who is worth a mere $810 million.

Not bad for someone who dropped out of business school in his sophomore year. Now, at 48, Combs has a multipronged career that covers not only fashion but music, TV production, athletes’ beverages and vodka. And, of course, he travels with his own entourage – at his WWD shoot, 17 people arrived well ahead of the star. Given all his activities, getting face time with Combs can be a challenge, hence the reason Scott Langton, Sean John’s vice president of design, arrived with storyboards and line sheets for the holiday 2018 collection, which he set up outside the dressing room for Combs to approve in between wardrobe changes.

The visuals encapsulated the brand’s past and future, an apt juncture for its 20-year anniversary. There was the Macy’s sportswear collection, whose customer is the brand loyalist who began wearing Sean John in the Nineties and never stopped. Those velour tracksuits and color-blocked sweatshirts are the brand’s cash cow, a more grown-up, tamer version of the streetwear that Millennials now embrace.

A new, elevated collection, aimed at attracting the consumer who shops at stores like Barneys New York, includes quilted and embossed black leather jackets and sharp suits, throwbacks to Nineties hip-hop videos and Sean John’s lavish runway shows, even taking inspiration from his latest Met Gala look. There’s also ath-leisure, but Made in the USA with elevated materials.

Combs arrived at the shoot a few hours later, in a matte-black chauffeured sedan. He was wearing a graphic T-shirt and jeans, and was relaxed and jovial. “Let’s do this,” he said. His crew turned up the hip-hop music and after quickly changing into a black Sean John tracksuit from the spring 2018 collection, he did a few jumping jacks, air punches and karate kicks to get warmed up. But something still wasn’t right.

“Everybody, I take my work very seriously, and I can’t concentrate with everybody talking really loud. I’m not trying to be, you know, we just need to work,” he said to the small crowd gathered in the photo studio. “Now can I hear some Public Enemy, please?” (The next look, a tailored three-piece suit, called for a mambo-inspired track.)

Combs has always had an ear for music and how it sets the mood. He started out throwing wildly successful parties during his college years and began his business career as an intern for Uptown Records. He founded his own label, Bad Boy Entertainment, in 1993 as a joint venture with Arista Records and there helped develop the careers of everyone from The Notorious B.I.G. to Faith Evans. Combs recorded his first music in 1997 under the name Puff Daddy and his debut single, “Can’t Nobody Hold Me Down,” hit number one and spent 28 weeks at the Billboard Hot 100 charts. His first album, “No Way Out,” boasted a tribute to The Notorious B.I.G., who was killed in November 1997, and was the first rap song to debut at number one. That album won Combs his first Grammy and he was on his way.

Today, as chairman and chief executive officer of Combs Enterprises, a portfolio of businesses and investments, he oversees Bad Boy Entertainment, Combs Wine & Spirits (Ciroc and Deleon), Aquahydrate, The Blue Flame Agency, Bad Boy Touring, Janice Combs Publishing, Revolt Films, Revolt Media & TV and Capital Prep Harlem. He’s also busy with other projects, most recently as a judge on Fox’s new music competition show, “The Four.”

But things were different in 1998, when he first decided to dabble in fashion. At that time the industry was ready to dismiss him as just another flash-in-the-pan celebrity play. But he had other ideas.

First off, he did his homework, cozying up to high-profile fashion figures such as Tommy Hilfiger and Anna Wintour before creating his own line.

“When I started, Tommy let me come into his office and ask a bunch of questions,” Combs said. “He served as my mentor. He let me look behind the curtain and learn.”

“I was first introduced to Puffy by my brother Andy,” Tommy Hilfiger said. “I saw him as a young, energetic, cool guy with an amazing spirit and at the time, he was wearing Tommy Hilfiger. He was very driven and focused on what he wanted to do in fashion,  which was to develop his own brand called Sean John. I helped him figure out a structure, knowing how important it was to have great factories and smart people to help with the journey. By introducing him to the right team, he became competition.

“Looking at him now, what he has done is epic,” Hilfiger added. “I am so happy to see him succeed. He truly is a one-of-a-kind American icon making world history.”

Combs also admired Karl Kani, whose eponymous collection was among the first to epitomize urban fashion. “He was a hero to black America,” he said. “His was the first designer name we knew about and he was a kid from Brooklyn, not a designer. But he represented a culture and a lifestyle.”

And it was in those footsteps that Combs followed with Sean John. “It’s not just fashion, it’s culture,” he said of his line.

Like Kani, Combs has never pretended to have a design background, but he had an uncanny sense of timing, jumping into the urban fashion scene when Fubu, Phat Farm, Ecko and others were racking up big sales. Sean John’s tracksuits, hoodies, overalls and fur-trimmed parkas were squarely on trend for the time, and appealed to the consumer who sought a deeper connection to the man behind the music. But he also offered up more finesse, with his tailored three-piece suits and ties and diamond-encrusted watches and earrings.

“I was fearless and I still am,” Combs said. “When we started, there were 30 brands doing what we did, but we’re the last man standing. I took risks and that’s what great fashion is all about.”

Combs may not be known for his modesty, but ego aside, there’s no getting around the fact that his line soon made its mark in the urban fashion arena.

Within two years, the Sean John brand was in 1,200 stores and had sales of $200 million. He graduated from the aisles at the MAGIC trade show in Las Vegas to multimedia extravaganzas on the runways of New York.

In 1999, Combs even appeared with Kate Moss and fashion’s elite — Jean Paul Gaultier, Karl Lagerfeld, Oscar de la Renta, Alek Wek and John Galliano — in an editorial in Vogue titled “Puffy Takes Paris,” shot by Annie Leibovitz. “That picture was the tipping point for me,” he recalled, adding that he only agreed to be photographed with the others if he could be in the center of the image.

In 2004, Combs silenced any remaining naysayers for good when he won the Council of Fashion Designers of America’s top men’s wear designer of the year award, beating out Ralph Lauren and Michael Kors. He had been nominated every year since 2000. That same year, he added a women’s collection to his men’s line, even hiring a designer from Polo Ralph Lauren to oversee it.

Although the men’s collection has changed since its early days, with more suits and furnishings than tracksuits, Combs is not surprised that it has had staying power.

“I found an untapped lane in fashion and that gave us a unique perspective to make things aspirational and fashion forward,” he said. “Look at the popularity of streetwear now with Gucci, Louis Vuitton, Balenciaga, Givenchy. Well, we were the first to launch it on the runways and embrace the aesthetic of the fashion of the street. Sean John was the most high fashion of the street brands.”

He also takes credit for launching what has now become a buzzword in the industry: fashiontainment.

He produced the first nationally televised runway show for Sean John during New York Fashion Week in 2001 that aired live on E! Television and the Style Network, and his show at Cipriani in 2002 cost $1.24 million and included “a specially commissioned video and soundtrack, theatrical curtains so massive that nine workers are required to hoist them, and custom hardwood bleachers and catwalk,” according to a fashion review in The New York Times.

In 2003, he spent $1.5 million on a show in New York that included an 800-module LED screen and a Plexiglass-covered runway. That was the same year that billionaire Ron Burkle invested an estimated $100 million into the brand through his Yucaipa Cos.

Nothing low-key for Mr. Combs.

“People were clamoring to get into my shows,” he recalled. “And the entertainment world embraced it.”

His marketing campaigns over the years have featured everyone from Pharrell Williams and Mariah Carey to Tyson Beckford, Naomi Campbell and Channing Tatum.

More recently, Combs has remained innovative, serving up what he says was the first-ever Instagram fashion show in 2013.

While the brand has lasted 20 years and still has annual retail sales in the U.S. of $525 million, Combs said that when he started out, there was a lot of negativity surrounding the idea of black or hip-hop fashion. “But it was never a negative to me,” he said. “You don’t call Gucci or Calvin Klein white fashion — it’s all fashion.”

To him, Sean John just represented the authenticity of Combs and his followers. “We were part of breaking down that door,” he said.

“People underestimate the power of belief and doing something artistic and from the heart and not thinking you’re in a box,” he said. And that strategy has served the company well over the past two decades.

“We’ve stayed focused and true to the brand,” he said. “We never followed trends. We were always about staying authentic and creating an emotional [connection] to that consumer and the community who looks like them.”

Combs has always embraced the details of the business and “studied all of the greats. I didn’t hold back or pull any punches. I came to slay and invigorate.”

And it worked.

“I was the first African-American to win a CFDA award,” he said. “That’s what separated me from being just a celebrity. I picked my own fabrics, worked on the sourcing, design and delivery. It’s different than just slapping your name on something.”

Combs said that while his business interests have expanded significantly since that time, fashion is “the most taxing of all the industries with the time and commitment it requires. If you miss a step, it can set you back one or two years.”

The Sean John business, like most, has certainly had its share of ups and downs. As the urban market cooled, the brand’s sales did as well. Additionally, the repeated attempts to launch a women’s collection were unsuccessful; Estée Lauder didn’t renew its licensee for the once-red hot Unforgivable fragrance; the 3,500-square-foot flagship on Fifth Avenue in New York was shuttered, and plans to expand internationally never took off. Jeffrey Tweedy, the company’s first employee and its current president, even departed the brand in 2005, only to return two years later. He remains at the helm.

But Combs persevered, and Macy’s, his brand’s most important retail customer, remains committed to the label.

Duran Guion, group vice president and fashion director of men’s and kids for Macy’s, said: “Sean John is one of the few pioneering brands that since the early emergence of streetwear two decades ago became a force to be reckoned with in the retail arena. As the brand celebrates a milestone anniversary, it continues to influence various aspects of music, lifestyle and popular culture. We are proud to congratulate Sean Combs and the entire Sean John organization as they celebrate a rich and vibrant history of iconic retail and fashion moments over the past 20 years.”

Since 2010, Sean John’s sportswear has been exclusive to Macy’s, available in more than 400 doors. Other products are sold at retailers including Dillard’s and Lord & Taylor.

The collection itself has also matured, trading in its full-blown disco suits and fur coats for more-tame sportswear and suits. It now operates under a licensed model with big industry names such as Peerless Clothing producing its suits and PVH Corp. doing its furnishings.

Emanuel Chirico, ceo of PVH, said of the label: “Sean John had built a great brand with a loyal following. Over the last 14 years, Sean John has been great partners to us at PVH. Together, we have worked with them to create fashionable dress furnishings that captures the essence of the brand and most importantly what the consumer needs and wants.”

But as his other business activities expanded, Combs decided in November 2016 to sell a majority interest in Sean John to Global Brands Group Holding Ltd., the publicly held Hong Kong-based company that holds the sportswear license. Combs is believed to retain a 20 percent stake in the brand. He knew that in order to achieve his goal of making Sean John a $1 billion brand with a global reach, retail stores and more categories, it was time to take on a partner.

“We got to the point where everything was changing in retail and our business model wasn’t beneficial to doing it on our own. Global Brands was already family, we’d been doing business with them since day one,” he said, so it made sense to sell the stake to that company.

Jason Rabin, president of North America for Global Brands, said his company has been working with Sean John for many years “and we felt we have a very strong relationship. They wanted a stronger partner so we invested. We feel the brand has a lot of opportunity, not just in the U.S., but globally.”

He added that the brand “has enjoyed extraordinary successes over the last two decades as one of the most impressive creative artists and lifestyle brands around the globe. We look forward to celebrating his anniversary and all of the exciting opportunities ahead.”

Combs stressed that despite selling a majority stake, he continues to be involved in the brand, providing input on design and marketing as well as some old-fashioned motivation to the team.

“My name is on it,” he said, “I can’t just walk away. But we put it into the right hands for the longevity of the business. I just thought it was time.”

With streetwear, particularly Nineties streetwear, a popular trend, Combs believes this is “a great time to be Sean John. We have a huge opportunity.”

The brand’s first collaboration of 2018, due in Macy’s this month, is a capsule that pays homage to artist Jean-Michel Basquiat, himself an icon of the era whose own trajectory and pop culture influence mirrors both hip-hop’s and Combs’. A black long-sleeved T-shirt emblazoned with Basquiat’s signature in red was the last look Combs chose to wear for the WWD shoot. “That’s so me,” he said, glancing at the image and echoing the phrase he used for all his favorite shots.

Although he’s no longer involved in the day-to-day operation of the brand, Combs still follows fashion intently, and says Ralph Lauren and Tom Ford remain his “go-to” brands. “And Gucci’s new designer [Alessandro Michele] is killing it,” he said.

He’s also proud that several Sean John alumni — Dae-Yi Chow and Maxwell Osborne of Public School and Christopher Bevans of Dyne among them — have gone on to create their own trend-setting brands. “I was happy to provide a platform for designers from different parts of the world and who could go on to pursue their dreams. That really touches me,” he said.

“Sean John was like grad school in aspiration 101,” Chow said. “It was the ultimate convergence of high and low and everything in between. It was an exciting time because everything we were doing in the beginning was new territory and hadn’t been done before. When people talk about disruption in fashion today, Puff was really the one who started that wave. He never subscribed to being labeled as just an ‘urban designer’ or a ‘black designer’ — he was way too ambitious for any one category. He knew how to deftly combine the worlds of culture, street and fashion. Every day was something new but it was incredibly demanding, he was never satisfied. I remember working on our fashion shows and it being the best of times and the worst of times.”

Osborne added: “My tenure at Sean John not only was pivotal to my design career but to my life. The atmosphere was electric, the energy infectious. We were poised for the unexpected. It was my first design job and the foundation that Sean John provided has kept me perennially encouraged. From Puff’s pioneering mentality to traveling the globe with a ‘design’ mindset for inspiration, it’s these bold declarations that still echo. Puff encouraged me to reach high and never settle. Working at Sean John taught fearlessness, to always push the culture forward and an indelible work ethic. These tenets set the framework for Public School. The experience was galvanizing; I started my career as an intern at Sean John and witnessed the first African-American to win a CFDA Award. It is on his shoulders on which we rest.”

Looking back at his 20-year run with Sean John, Combs is happy that he was able to achieve what he set out to accomplish, which was to prove it’s possible for African-Americans to be successful — really successful.

“This is my calling — I’m here to give hope,” he said. “I built Ciroc [vodka] from $30 million to more than a $1 billion business, and we launched our own tequila, which was audacious, and with Revolt, I have the only black majority-owned network. But I don’t let anything stop me.”

Combs said he is perhaps proudest of his charter school in Harlem that provides an education for underprivileged children so they, too, can make a difference in the world.

“That’s in my DNA. I hustle and I go in and make changes in industries and I will continue to do so. So the next 20 years will be about continuing to change the narrative of the hip-hop and African-American communities and culture.”

His parting advice? “Have fun and be fashionably fly when you’re doing it.”

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