Rihanna Opens Up About Her Style Evolution—And The 2000s Trend She Regrets The Most

by Coco

Rihanna has never been one to shy away from bold fashion choices. Known for her daring, sometimes unconventional, and always unapologetic style, the superstar has been a trendsetter for over a decade. But even she has moments when she looks back and wonders what in the world she was thinking.

In a candid TikTok interview with fashion enthusiast Mystery Fashionist on Dec. 23, Rihanna opened up about her style evolution, dishing on everything from her favorite wardrobe staples to the fashion trends she now regrets. And let’s just say, she’s not afraid to poke fun at herself when it comes to some of her past fashion missteps.

The 36-year-old mother of two gave fans a taste of her current, ultra-chic look, rocking a khaki suede coat with fur lining, paired with black baggy pants, pointed-toe heels, and a baseball cap. The finishing touches—a bulky black leather belt and an emerald green handkerchief—gave the ensemble a sophisticated edge. Rihanna was clearly pleased with her outfit, which she described as “giving a little Christian Dior” while giving it a solid 10 out of 10.

She praised the outfit for its “sleeves” and highlighted her YSL pants, boots, and the belt. But despite her impeccable present-day style, when asked about her past fashion choices, Rihanna wasn’t quite as forgiving.

When the TikTok interviewer asked Rihanna about the one fashion trend she regretted embracing, she responded with a laugh. “Oh my God, why y’all gotta bring up old s—,” she quipped, before diving into a notorious fashion era.

Rihanna confessed that her early days, when she was often spotted wearing baggy jeans with her underwear peeking out, were a serious “what was I thinking?” moment. “When I first started, and I was wearing like the baggy jeans, with the panties out… What the f— was I thinking?” Rihanna said with a chuckle, adding that she’s definitely glad to leave that look behind.

The trend, which was iconic during the early 2000s, has actually made a bit of a comeback in recent years. But for Rihanna, the look is firmly in the past. She even ran her hand over the thick leather belt she was wearing during the interview and joked that it was a far cry from the days of letting her underwear peek out from beneath her baggy jeans. “It’s called growth, y’all!” she added, proudly displaying how far her fashion has come.

Rihanna’s transformation from the daring “Bad Gal” who rocked streetwear with confidence to a true fashion icon has been one of the most exciting style evolutions in recent years. From launching her groundbreaking Fenty fashion line to serving as the face of countless high-fashion campaigns, the singer has shown an unshakable commitment to redefining what it means to be a trendsetter.

While she admits to having some style regrets, she also shared a few pieces she simply can’t live without today, including a trusty New York snapback, baggy jeans (with the underwear securely hidden), fitted vintage jeans, and, of course, her signature “little speedy croc LV-monogrammed bag.” Oh, and let’s not forget her Savage X Fenty underwear, which she swears by for comfort and style.

It’s clear that Rihanna’s journey through fashion is far from over, and as she continues to dominate both the music and fashion worlds, her fans can look forward to even more groundbreaking, and sometimes regret-free, looks.

Whether you’re reminiscing about her early 2000s style or marveling at her current, sophisticated aesthetic, Rihanna’s fashion evolution is nothing short of inspiring. And while she may cringe at some of her past choices, one thing is for sure: she’s only getting better with age.

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