Sean Combs’ future may be in limbo as the hip-hop entrepreneur remains in jail awaiting trial on federal charges of racketeering, sex trafficking and transportation to engage in prostitution. But the high-profile allegations, to which he has pleaded not guilty, have once again focused attention on Combs’ colorful past in the fashion world and his Sean John apparel brand.

In 1998, Combs was already well known as a successful hip-hop artist and the founder of Bad Boy Entertainment, a joint venture with Arista Records that helped develop the careers of The Notorious B.I.G. and others.

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It was also the year that he launched Sean John, his own fashion brand.

Although the fashion industry was prepared to write off his venture into their world as another flash-in-the-pan celebrity brand, Combs was serious about growing and maintaining his presence in the fashion arena and he rode the wave for more than 20 years.

Here, a timeline of the ups and downs of the Sean John brand.

1998: The Sean John label is launched as an urban fashion line. The initial collection comprises 11 pieces, including denim, coveralls, twill and linen bottoms, linen and silk shirts, velour hook-ups (zip front jacket and pant), tees and a Sean John signature baseball cap.

1999: The Sean John label debuts at retail with a launch event at Bloomingdale’s. Combs appears with Kate Moss, 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.

2000: Combs accompanies Jennifer Lopez, his girlfriend at the time, to the Grammy Awards where she wears a green silk chiffon Versace dress open to her navel, which instantly becomes an iconic image. Sean John holds its first fashion show at Bryant Park during New York Fashion Week. Sean John is nominated for the CFDA Perry Ellis Award for Menswear.

2001: Combs spends more than $1 million to produce the first nationally televised runway show for Sean John during New York Fashion Week that airs live on E! Television and the Style Network. Sean John launches underwear at Bloomingdale’s. Combs cancels a planned Paris runway show, slated for January 2002, in order to support the fashion community in the wake of the Sept. 11 terrorist attacks.

2002: The Sean John show at Cipriani in New York costs $1.24 million and includes “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.

2003: Combs spends $1.5 million on a New York show that includes an 800-module LED screen and a Plexiglass-covered runway. Billionaire Ron Burkle’s Yucaipa Cos. invests a reported $100 million in the Sean John brand. Combs is nominated for Menswear Designer of the Year by the CFDA. Combs announces he will run the New York City Marathon to raise more than $1 million for children’s charities. Among his sponsors are McDonald’s, Nike and MTV.

2004: Combs wins the CFDA’s top menswear designer of the year award, beating out Ralph Lauren and Michael Kors. Sales of his brand reach $450 million at retail. Sean John opens a 3,500-square-foot flagship at 475 Fifth Avenue in New York. Combs appears on Broadway in “Raisin in the Sun.” Sean John acquires a 50 percent stake in Zac Posen’s company, Outspoke LLC.

2005: Combs attempts to launch womenswear for the first time but the Sean by Sean Combs line is shuttered less than a year later. Combs inks a deal with CBS Sports to dress its on-air personalities in Sean John for the 2006 NCAA basketball tournament.

2006: He launches Unforgivable, a fragrance created with Parlux Fragrances and licensed to the Estee Lauder Cos. The ad campaign features Combs in bed with two women. Combs is honored by the Accessories Council as Fashion Influencer of the Year. Sean John signs a sleepwear license with Basic Resources.

2007: Unforgivable wins Fragrance of the Year in the men’s luxe category at the FiFi Awards hosted by The Fragrance Foundation. Sean John launches Unforgivable Woman.

2008: After a five-year absence, Sean John returns to the runway. The company debuts “If I were King,” a fashion show documentary on MTV. Sean John announces Nelly as the new spokesmodel for Sean John underwear and loungewear.

2009: Sean John launches “I Am King” fragrance.

2010: Macy’s signs a deal with Sean John to become the exclusive retailer for the brand’s sportswear.

2010: The Fifth Avenue Sean John store closes.

2012: Sean John signs a footwear license.

2013: Combs offers up what he claims is the first-ever Instagram fashion show.

2013: Estee Lauder declines to renew the Sean John fragrance license and it is taken over by Jacavi.

2015: Sean John signs license with EVY of California for children’s apparel and launches 3 AM fragrance.

2016: Global Brands Group Holding Ltd. purchases a majority stake in Sean John and Combs earns an estimated $70 million. Sean John’s retail sales exceed $525 million in the U.S.

2021: Combs files a lawsuit against Global Brands Group seeking $25 million for “false endorsement, misappropriation of likeness and violating his publicity rights,” over the launch the prior fall of a women’s collection with U.K. fast-fashion retailer Missguided Unlimited.

2021: After Global Brands Group files Chapter 11, Combs buys back the trademark for the Sean John brand in bankruptcy court for $7.551 million.

Launch Gallery: A Look Back at Sean John Through the Years

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