Rihanna has long been a fashion icon, but her style evolution has seen drastic shifts over the years. One of her most memorable fashion moments happened during New York Fashion Week in 2009, when she fully embraced the edgy aesthetic that defined the late 2000s. Attending the World of Giuseppe Zanotti party, the then 21-year-old singer made a bold statement in an Alexander Wang hooded mini dress, Giuseppe Zanotti x Balmain shoes, and studded sunglasses by A-Morir—a look that embodied both glamour and rebellion.

The Fashion’s Night Out Phenomenon
The event took place during Fashion’s Night Out, an initiative launched in 2009 as part of NYFW, where designers, celebrities, and editors transformed New York City into a shopping spectacle. With Anna Wintour as the driving force, the event aimed to revitalize retail and create a buzz around high fashion. Rihanna’s appearance at the Giuseppe Zanotti party was a standout moment, reinforcing her reputation as a trendsetter unafraid to push boundaries.

A Look That Defined an Era
Rihanna’s 2009 aesthetic aligned perfectly with her fourth studio album, Rated R, which introduced a darker, more rebellious side of the artist. Her all-black ensemble, combined with statement accessories, mirrored the grunge-glam fusion that was rising in popularity at the time. The studded sunglasses by A-Morir, retailing today for $350, added an unmistakable rockstar edge to her look.

Rihanna: From Style Icon to Fashion Mogul
Since her early days in the music industry, Rihanna has cemented herself as a power player in both music and fashion. While her music career catapulted her to international stardom, her eye for style and entrepreneurial ventures have been equally influential. She pioneered inclusive beauty with Fenty Beauty, one of today’s most celebrated makeup brands, and expanded into the fashion world with Savage X Fenty, a lingerie empire valued at $1 billion.

The Return of 2000s Fashion
With Y2K trends making a major comeback, Rihanna’s 2009 edgy aesthetic feels more relevant than ever. From McQueen’s Skull scarves to Tory Burch Claire flats, early 2000s fashion staples are once again hitting the runways. While it remains to be seen if Rihanna’s grunge-glam phase will resurface in today’s style scene, one thing is certain: her impact on fashion is timeless.

As rumors swirl about her return to music, one can only wonder—will she also revive this iconic era of her fashion journey?