Rihanna Says This Very 2000s Outfit Is the One She Regrets the Most: 'What the F-- Was I Thinking?'

Mar. 15, 2025

Rihanna in 2005 at the Teen People Listening Lounge.Photo:Kevin Winter/Getty ;Brad Barket/Getty

Kevin Winter/Getty ;Brad Barket/Getty

Rihannais looking back on her style evolution.On Monday, Dec. 23, TikTok userMystery Fashionist spoke to the singerabout her style choices – past and present. The mom of two is widely known for herdaring,trailblazingand evenempoweringlooks and fashion philosophies.For the video interview, Rihanna, 36, donned a khaki-colored suede coat with fur lining, and paired it with black baggy pants, a baseball cap and pointed toe heels. She wore an emerald green handkerchief tied around her neck and kept her hair down, and finished the look with a bulky black leather belt with silver hardware.“I love it. It’s giving a little Christian Dior,” she said about her outfit that she rated a 10, pointing out the sleeves of her jacket. She also highlighted her YSL pants, boots and belt.Rihanna in 2005.Brad Barket/GettyThe Fenty founder told Mystery Fashionist she can’t live without a good New York snapback, both baggy jeans and fitted vintage jeans, “the little speedy croc LV-monogrammed bag” and Savage X Fenty underwear.When the TikToker asked her what fashion trend she regretted taking part in, she replied, “Oh my God, why y’all gotta bring up old s—.“Rihanna in 2005.Kevin Winter/GettyNever miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.He noted that many of the people he interviewed in the past often mentioned the sweatpants and heels combination in response to this question — but Rihanna adored that trend, she said, “especially now as a mom.““When I first started, and I was wearing like the baggy jeans, with the panties out,” she said. “What the f— was I thinking?“It’s an older trend, but has resurfaced in recent years, the interviewer said.But Rihanna said she’s happy to leave the trend behind. She ran her hands over her thick leather belt — about where she used to let her underwear pop out.“It’s called growth, y’all!” she said.

Rihannais looking back on her style evolution.

On Monday, Dec. 23, TikTok userMystery Fashionist spoke to the singerabout her style choices – past and present. The mom of two is widely known for herdaring,trailblazingand evenempoweringlooks and fashion philosophies.

For the video interview, Rihanna, 36, donned a khaki-colored suede coat with fur lining, and paired it with black baggy pants, a baseball cap and pointed toe heels. She wore an emerald green handkerchief tied around her neck and kept her hair down, and finished the look with a bulky black leather belt with silver hardware.

“I love it. It’s giving a little Christian Dior,” she said about her outfit that she rated a 10, pointing out the sleeves of her jacket. She also highlighted her YSL pants, boots and belt.

Rihanna in 2005.Brad Barket/Getty

Brad Barket/Getty

The Fenty founder told Mystery Fashionist she can’t live without a good New York snapback, both baggy jeans and fitted vintage jeans, “the little speedy croc LV-monogrammed bag” and Savage X Fenty underwear.

When the TikToker asked her what fashion trend she regretted taking part in, she replied, “Oh my God, why y’all gotta bring up old s—.”

Rihanna in 2005.Kevin Winter/Getty

Kevin Winter/Getty

Never miss a story — sign up forPEOPLE’s free daily newsletterto stay up-to-date on the best of what PEOPLE has to offer​​, from celebrity news to compelling human interest stories.

He noted that many of the people he interviewed in the past often mentioned the sweatpants and heels combination in response to this question — but Rihanna adored that trend, she said, “especially now as a mom.”

“When I first started, and I was wearing like the baggy jeans, with the panties out,” she said. “What the f— was I thinking?”

It’s an older trend, but has resurfaced in recent years, the interviewer said.

But Rihanna said she’s happy to leave the trend behind. She ran her hands over her thick leather belt — about where she used to let her underwear pop out.

“It’s called growth, y’all!” she said.

source: people.com