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Style Evolution: How Rihanna Upgraded Skinny Jeans with Baggy Designer Fits

A 9-time Grammy Award-winning artist, disruptor of beauty and lingerie industries, Super Bowl halftime performer, mother of two, and billionaire—Rihanna is a lot of things.

She is also a millennial, a trait evident in her denim style evolution. Before the denim coordinates by Louis Vuitton and Y/Project denim gowns that have made Rihanna one of the most influential style stars, there were skinny jeans.

The Barbadian singer landed on the US Billboard Hot 100 for the first time in 2005 with her debut single “Pon de Replay,” wearing low-rises, micro denim shorts and Miss Sixty skinny jeans. The body-hugging jeans, styled with an embellished top, statement belt or belly chain, became Rihanna’s de facto stage look for the next few years as the world got to know her unique blend of dance-pop, reggae, EDM and R&B.

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As the hits rolled in, the skinny jeans remained even as she was named the 2014 CFDA’s “Style Icon.” During the next decade, Rihanna was seen jetting in and out of cars wearing dark wash, ripped and distressed skinnies, occasionally tucked into over-the-knee boots.

That began to change in 2020, however. Rihanna, like most women, emerged from the pandemic lockdown wearing straight and relaxed-fit jeans. By 2021, she shifted gears once again, putting her spin on maternity denim as she expected her first son, RZA, with beau A$AP Rocky.

“For her first pregnancy reveal, she wore these long sweeping denim pants, too impractical to walk in let alone on the streets of New York in the snow,” said Kyle Lamar Rice, fashion writer. “Though the style signified the idea of casually out and about, the trailing of the pants like a gown on the carpet, when matched with the sweeping pink Chanel jacket, felt much more regal on display.”

The exaggerated denim fits carried into her second pregnancy in 2023. Rihanna dressed in Louis Vuitton’s pixelated print denim boiler suit and bra top to take in Pharrell Williams’ first runway show as the French fashion house’s men’s creative director. For a shopping trip to Target, she elevated a classic New York look—dark wash baggy jeans, wheat Timberland boots and a New York Yankee cap—by adding a fur coat.

“There’s something to be said about the grandeur of Rihanna’s maternity looks. They’re never simply stated, spotlighting vintage Chanel and Christian Lacroix, and almost always feature a denim piece,” Rice said.  

Expect to see more glam and oversized denim looks from Rihanna, who since giving birth to their second son Riot Rose last year, has been sporting ripped jeans with satin coats and Loewe track jackets tucked into Balenciaga’s destroyed super large baggy jeans.

This story was published in Rivet magazine. Click here to read more.