Rihanna Revealed the One 2000s Fashion Trend She Regrets Wearing

Rihanna is a bonafide fashion icon, but even the most enviable style stars have a few fashion faux pas they'd never wear again.

The Fenty Beauty founder caught up with TikToker Mystery Fashionist and was asked what fashion trend she regretting participating in. "Dear God, why you gotta bring up old shit?" Rihanna replied, exasperated. The interviewer went on to say that the sweatpants and heels trend is how most people often answer that question to him, but Rih was slightly insulted. "I started that trend, the fuck? I would never regret that that," she explained, adding that "especially now as a mom. A heel is the best fucking thing I could do for my pajamas."

As for the 2000s trend that she does regret, Rihanna revealed that she often cringes when looking back at her debut era outfits. "When I first started, and I was wearing like the baggy jeans, with the panties out," she said. "What the fuck was I thinking? I can't wear it for the evolution. It's called growth, y'all."

It isn't very often that Rihanna has style regrets, but it has happened. She previously revealed that boyfriend A$AP Rocky had made her feel insecure in her own fashion. “I be feeling bummy as shit next to this man. I feel like, goddamn, I look like his assistant,” she joked while speaking with Interview magazine for its spring 2024 issue. “I’m getting on a plane. We should be in sweats. He wants to be in a full Bottega suit. I’m like, 'Why you got to do that to me?'” Rihanna added.

Rihanna is more relaxed with her fashion now, which comes from making sure her kids look good first—“It’s more like I spend my time getting the kids dressed to death, and then I’m like, ‘What’s the most comfortable outfit to wear around them? What’s not going to feel uncomfortable on their face or on their body or make me feel like I can’t hold them properly?’ Moms are lazy dressers in real life.”

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