There is no debate when it comes to Rihanna’s style. The business mogul and singer-songwriter has turned her personal brand into some of this generation’s most successful business ventures. Aside from selling multiple chart-topping albums and writing the rule book on modern-day celebrity, the Barbados native has undeniably become a beauty and fashion style icon for the 2000s and beyond.
“I’ve been slowly evolving throughout the fashion world. First wearing it, buying it, being recognized for my style and then collaborating with brands,” the singer told The New York Times back in 2019. Before co-hosting the 2018 Met Gala, starting her own luxury brand with LVMH, and completely turning the lingerie industry on its head, Rihanna started out on the fashion scene during her “Pon de Replay” debut in 2005 and pioneered so many classic styles of that era, from crop tops and low-rise jeans to waistcoats and bubble-hem mini skirts.
As early-aughts style continues to make its comeback decades later, who else better to look to for inspiration than the bad gal herself? Ahead, see her best Y2K fashion moments through the years.
2005, Alliance’ Music UpFront
Wearing a graphic cropped zip-up jacker with super low-rise faded jeans and silver bangles on her wrist in 2005.
2005, MTV Video Music Awards
Wearing low-rise white skinny jeans with a sheer cut-off tank underneath a bejeweled cropped knit vest with big gold hoops and bangles to match to the 2005 MTV VMAs.
2005, T4 Poll Winners’ Party
Paying homage to Michael Jackson, Rihanna wore a single moto glove to match her metallic gold bra top and gold belt at the T4 Poll Winners’ Party in 2005.
2005, Teen People Listening Lounge
The singer wore a tie-dye halter top to match the hipster underwear peeking through her low-rise jeans, along with pink Converse to finish off her look at the Teen People Listening Lounge in 2005.
2005, KIIS FM Jingle Ball
Wearing a white and gold-embroidered cropped vest with a single gold glove, a skinny gold belt, and jeans to the KIIS FM Jingle Ball in 2005.
Wearing an striped halter-neck dress with a gold link chain and silver sequin shoes to the MuchOnDemand show in 2006.
2006, Teen Choice Awards
Wearing an indigo blue mini dress with silver heels to the Teen Choice Awards in 2006.
2006, MTV Video Music Awards
Wearing a white corset top with a cream and sequined mini skirt with open-toe heels to the MTV VMAs in 2006.
2006, MTV Movie Awards After Party
Wearing a strapless mini dress with a patterned top, hot pink belt, and black skirt with studded heels to the MTV Movie Awards After Party in 2006.
2007 MTV VMAs Nominations
To promote her single “Umbrella,” Rihanna carried a cane with a white corset top and black low-rise wide-leg pants to the MTV VMAs Nominations event in 2007.
2007, MTV’s TRL
Wearing a gray knitted hat with a corset top tucked into faded gray jeans to MTV’s TRL studio in 2007.
2008, Nickelodeon’s Kids’ Choice Awards
Wearing a polka-dotted corset top with low-rise tapered pants and platform heels to Nickelodeon’s 2008 Kids’ Choice Awards.
2008, Milan Fashion Week
Sitting front row at the Gucci Spring 2009 show, Rihanna wore a halter shift dress and knee-high boots with fringe during Milan Fashion Week in 2008.
2009, Los Angeles
Wearing a light blue dress shirt tucked into an A-line mini skirt with pearl necklaces to match in Los Angeles in 2009.
2009, New York City
Wearing a cropped sleeveless blazer and beige harem pants with Louboutin heels.
2009, Paris Fashion Week
Wearing layered Chanel necklaces over a corset top tucked into a pencil skirt with a Chanel fur muffler to the Chanel Spring 2010 show at Paris Fashion Week in 2009.