Getty Images / MARTIN BUREAU

In May this year, Rihanna unveiled her first Fenty collection since launching her own label under the LVMH umbrella, releasing a lookbook just weeks after the announcement of her luxury fashion house had attracted headlines around the world.

Featuring power suits, oversized silhouettes, and streetwear-inspired garms, the first Fenty collection under LVMH was a culmination of Rihanna’s 14 years in the entertainment industry, from 2005, when she was signed to Def Jam by JAY-Z and released first single “Pon de Replay,” to high-profile collaborations with PUMA, awards, her Savage x Fenty lingerie line, the Fenty Beauty cosmetics brand, and everything in between.

With Fenty opening its first US pop-up, here we take a moment to reflect on all the pivotal moments that have carried Rihanna from pop star to fashion powerhouse.

Getty Images / Evan Agostini

1988: Robyn Rihanna Fenty is born

Rihanna was born on February 20, 1988 to Monica and Ronald Fenty in Saint Michael, Barbados. She’s of Afro-Barbadian, Afro-Guyanese and Irish descent, and has two brothers, two half-sisters, and a half-brother.

Her dabbles in entrepreneurship started young. “She used to sell stuff on the side of the street like I did,” her father once said. “She’d come outside of the store and put up a rack and sell hats and belts and scarves. She would also buy sweets, put them in packages and take them to school to sell to her friends for a profit.”

2003-2005: Rihanna is discovered and signs with Def Jam

Rihanna was discovered by Evan Rogers in 2003, who sent a demo recorded over the next year to JAY-Z, at the time president and CEO of Def Jam Recordings. In 2005, still just a teenager, Rihanna was called in to audition for JAY-Z in his office in New York.

“And that’s when I really got nervous,” she told The Guardian in 2007. “I was like: ‘Oh God, he’s right there, I can’t look, I can’t look, I can’t look!’ I remember being extremely quiet. I was very shy. I was cold the entire time. I had butterflies. I’m sitting across from JAY-Z. Like, JAY-Z. I was star-struck.

“The audition definitely went well. They [Def Jam] locked me into the office — till 3 a.m. And JAY-Z said, ‘There’s only two ways out. Out the door after you sign this deal. Or through this window.’ And we were on the 29th floor. Very flattering.”

2007: Rihanna wins her first Grammy

A year after scoring her first number one single with “SOS,” Rihanna bagged her first Grammy, winning Best Rap/Sung Collaboration for “Umbrella,” which featured JAY-Z. The video delivered an early glimpse of the Bad Girl persona we know and love today, hinting at a new, rebellious era.

2011: Rihanna releases her first fragrance

In January 2011, Rihanna launched her first fragrance, Reb’l Fleur, which came with the tagline “Good feels so bad, bad feels so good.” Two other perfumes, Rebelle and Nude, followed in 2012, and a fourth, Rogue, came a year later. The fragrances were part of a licensing deal with Parlux Fragrance, which also saw the release of signature scents by Kanye West and JAY-Z.

2011: Rihanna becomes the face of Armani

In September 2011, Rihanna was announced as the face of the FW11 Armani Jeans and Emporio Armani underwear campaigns, following in the footsteps of Megan Fox and Victoria Beckham.

2013: Rihanna produces and stars in fashion design reality show Styled to Rock

In 2013, Rihanna starred in and executive produced reality TV series Styled to Rock, a show in which contestants competed to create outfits for various musical acts.

At the time, she told Glamour, “I felt like there were all these talented people in New York who had a very keen eye for style and design, but I couldn’t find them. I get excited by discovering new designers.”

2013: Rihanna launches her first collaboration with MAC Cosmetics

Rihanna’s first big cosmetics endeavor came when she signed a deal with MAC Cosmetics. The first product to drop was a red lipstick that sold out in three hours.

In late 2013, she bulked out her initial RiRi for MAC offering, adding new matte lipstick shades, eyeshadows and eyeliners, bronzing powder, and nail varnish.

2013: Rihanna designs first collection for River Island

The fast-rising entrepreneur’s debut collection for British fashion retailer River Island in SS13 was another huge success and was followed by a FW13 collection.

“I made a piece for every person in my crew,’ she told Elle ahead of her second SS13 drop. “We all have different body shapes and different tastes and some of us are braver than others, but I think like that because that’s how women in the world are. We’re all different and we all like different things and we all have different occasions, different moods, and different body types.”

2013: Rihanna becomes the face of Balmain

Balmain creative director Olivier Rousteing called Rihanna an “icon” after selecting the singer as the face of the label’s SS14 campaign, telling Vogue, “In front of the camera, she makes you feel like she is the only girl in the world. When the woman that inspires you wears your creations, your vision feels complete.”

2014: Rihanna wins CFDA Fashion Icon Award

Stamps of approval don’t get much more indelible than being presented the CFDA Fashion Icon Award by Vogue editor-in-chief Anna Wintour, which is exactly how Rihanna’s position in fashion was cemented in 2014.

During her speech, Wintour spoke of Rihanna’s ability to speak to fans through sartorial means: “She proves that incredible style can help take a talented young woman from a small island to the world stage, and along the way spark a lot of conversation about elegance and empowerment.”

2014: Rihanna is named creative director of PUMA

Getty Images / John Sciulli

In December 2014, Rihanna was named creative director of PUMA, overseeing the sportswear brand’s women’s line, with a focus on fitness and training apparel. She was also named a brand ambassador alongside star athletes Usain Bolt and Mario Balotelli. Like the MAC collaboration, Rihanna’s first PUMA shoe, the Creeper, sold out in three hours.

2015: Rihanna becomes the first black woman to front a Dior campaign

When Rihanna was selected to star in Dior’s “Secret Garden” campaign, which showed models posing around Versailles in France, not only did it mark another major luxury brand endorsement, but it was also the first time the French house had chosen a black woman to front a campaign. The following year, she also created a range of sunglasses for the brand.

2015: Rihanna launches beauty and style agency Fr8me

The launch of Fr8me was perhaps the first indication that Rihanna wasn’t playing around when it came to carving her own territory in fashion and cosmetics. Fr8me, launched with managing partner Benoit Demouy, was a beauty agency built to help stylists, hairdressers, and makeup artists book editorial and celebrity jobs.

“I am very involved with that part of my process, so this agency was an organic thing for me to do,” she explained to The Hollywood Reporter.

2016: Fenty PUMA debuts at New York Fashion Week and Rihanna wins Shoe of the Year

Fenty PUMA made its debut at New York Fashion Week FW16. Alongside the Creeper platform sneaker, Rihanna presented a number of Japanese sportswear-inspired pieces that riffed on her signature style and were coveted the world over. The PUMA Creeper was even crowned Shoe of the Year at that year’s Footwear News Achievement Awards.

2016: Rihanna x Manolo Blahnik collection drops

Rihanna embarked on a new, denim-focused partnership with Manolo Blahnik in 2016, comprising a range of shoes that featured sequins and embroidery inspired by her tattoos. The collab was titled “So Stoned” and again proved so popular that the collection’s dedicated microsite crashed several times upon release.

2017: Fenty Beauty launches, catering to women of all colors

Getty Images / Mark Ganzon

Rihanna inked her first LVMH deal in 2017 for the launch of Fenty Beauty, a cosmetics line that vastly enhanced the diversity of the beauty industry. Rather than releasing various shades of beige, as most brands were wont to do, Fenty Beauty offered 40 different foundation shades, later expanded to 50, making Fenty Beauty one of the most inclusive beauty brands on the market.

2017: Rihanna designs jewelry for Chopard

A luxury jewelry collection with Chopard marked Rihanna’s next high-end collaboration. Rihanna Loves Chopard debuted at the Cannes Film Festival and featured a number of one-of-a-kind pieces that drew inspiration from the singer’s Barbadian roots.

2018: Savage x Fenty lingerie line arrives

“The concept really is just about exploring and celebrating women and all different shapes and bodies, and designing things that met that,” Rihanna explained to WWD after her lingerie line launched at New York Fashion Week FW18.

The show was one of the best presentations of the season. Inclusive as always, it saw the likes of Gigi and Bella Hadid, Joan Smalls, and a heavily pregnant Slick Woods all decked out in Rihanna’s fierce creations.

Getty Images / Ilya S. Savenok

2019: LVMH makes Fenty a luxury house

Every achievement on this list led up to Rihanna’s latest and biggest deal: the launch of her own luxury fashion house, Fenty, under the LVMH banner. It marks the first time LVMH has built a new label from scratch with a black woman at the helm.

Comprising ready-to-wear, leather goods, and accessories, Rihanna’s Fenty offerings have already started to drop, and the label is now heading Stateside with a New York pop-up. Revisit the first collection’s full lookbook here.

Senior Staff Writer
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