Rihanna’s Most Daring Looks Throughout Her Career

Rihanna tricked the eye in a glamorous gown at the 53rd Annual Grammy Awards in February 2011.

For her fourth Grammys red carpet appearance, Rihanna stepped out in a white frill and semi-sheer gown on February 13, 2011. Under the figure-hugging gown, which was created by couture designer Jean Paul Gaultier, the singer wore pasties and ski-colored underwear to trick the eye into believing she was fully bare. Her red lob haircut and red lip beautifully contrasted the white gown.

Later in the night, the singer performed one of her and Drake’s songs, “What’s my Name,” and went on to win best dance recording for “Only Girl (In The World).”

In November 2013, she wore a sparkling bra top to accept the first-ever AMAs icon award.

Rihanna wore yet another daring Jean Paul Gaultier look to the American Music Awards on November 24, 2013. The two-piece ensemble had a plunging, beaded bra top and matching skirt that flared out in a mermaid style with sheer lace. Her doobie wrap hairstyle also got people talking because it’s a style African American women typically wear in the privacy of their homes, according to Elle.

She wore the revealing look on the red carpet as well as onstage to accept the first-ever AMAs icon award.

Her refined — yet revealing — look stunned at the 2014 Met Gala.

Rihanna has become a fashion icon and staple at Met Gala events because she shows out every year. In one of her earlier appearances, at the “Charles James: Beyond Fashion”-themed Met Gala on May 5, 2014, the singer wore a stunning two-piece look.

The white Stella McCartney creation was structured yet flowing and refined yet revealing, showcasing the singer’s abs and back. Paired with a crystal choker and loose updo, Rihanna looked angelic.

Rihanna’s “naked dress” worn to the CFDA Fashion Awards in June 2014 will go down in history as her most daring.

Rihanna’s most daring look of all time — so far — is hands down the “naked” Adam Selman dress that she wore to the 2014 CFDA Fashion Awards.

The form-fitting dress covered in Swarovski crystals broke the internet because the sheer material revealed the singer’s bare breasts and flesh-toned underwear. The coordinating holographic-like gloves and headpiece and the fur shawl gave a fresh spin on old Hollywood glam.

The now-iconic look was only fitting as Rihanna attended the event to accept the CFDA’s fashion icon award.

Rihanna spoke to Vogue in a March 2016 interview, reminiscing over the look. She said she wishes she wore a bedazzled thong instead, saying, “That’s the only regret I have in my life.”

She looked like a cupcake in a voluminous gown at the 57th Annual Grammy Awards on in 2015.

Rihanna was lovingly compared to a cupcake after she appeared in a bubble-gum pink Giambattista Vali dress at the Grammys in February 2015. A dramatic two-tiered, textured skirt poofed out from a simple bandeau-like top. With fresh, dewy makeup and her hair pulled back, Rihanna let the dress be the star of the show, somehow not overpowering her.

The singer went on to perform her and Eminem’s single, “The Monster,” that night and win best rap/sung collaboration for it.

The singer stepped out in her best pajama set in New York City on July 17, 2015.

In one of her “that girl” moments, Rihanna strutted the streets in a silk pajama set. On her way to her recording studio, the singer wore the floral-print pink set with a white lace bra, furry heels, and a glass of wine.

The singer has since created an empire with Savage X Fenty, her lingerie brand, which also sells pajamas and loungewear.

She was not discreet when she walked in London with an oversized puffer coat on August 19, 2016.

Despite it being August, the singer opted for an oversized Raf Simons puffer jacket for a shopping spree at Harrods in London, England. Rihanna has worn quite a few dramatic puffer coats. For this occasion, she paired a black patent leather one with yellow sneaker-inspired, lace-up booties.

Rihanna showed the love in a red heart coat on September 5, 2016.

In yet another iconic fashion moment for the singer, she wore a red, furry, heart-shaped coat in September 2016. After leaving the Saint Laurent Autumn/Winter 2016 showcase, she was seen walking in New York City in the brand’s $15,500 coat. She paired the luxurious and quirky outerwear with cut-off denim shorts, strappy heels, and a dad hat.

Her rib-cage tattoo was on full display at the 2017 Grammys.

On February 12, 2017, at the 59th Annual Grammy Awards, the singer arrived in a stunning Armani Privé ensemble. The orange crystal halter bra top exposed her tattoo of Egyptian goddess Isis on her upper rib cage. A highwaisted, full, and ruffled black skirt added even more drama to this look.

Although nominated for eight awards that night, she did not leave with any.

Rihanna stuck to the avant-garde theme for the Met Gala in May 2017.

Yes, Rihanna did it again at the Met Gala. For the 2017 “Rei Kawakubo/Comme des Garçons: Art of the In-Between” theme, Rihanna wore an avant-garde Comme des Garçons creation.

The architectural and whimsical look, which included petal-like pieces of fabric that built on each other, was paired with over-the-knee strappy heels and styled with a top knot and flushed eyeshadow and blush.

The next day, beading and feathers made up another daring “Valerian” press-tour look.

For the France premiere of “Valerian,” the actress may have toned down the volume, but she amped up the embellishment. She wore a pastel pink Prada two-piece with a crystal-beaded bodice and a complementary skirt with feathers galore. This embellished look was only made more dramatic with Rihanna’s pink sunglasses and fur-covered strappy heels.

The singer has worn the double-denim trend on multiple occasions while visiting New York City.

Rihanna is a fan of denim on denim, no matter if it’s a “Canadian tuxedo” or a co-ord set. She rocked the look for her “FourFiveSeconds” music video, but she’s also worn it on the streets.

On September 8, 2017, she wore thigh-high denim boots by Y/Project with an oversized shirt-dress in New York City.

The following month, she wore a Tom Ford co-ord set with a cropped jacket, mini skirt, and a pair of denim boots when out in the city again.

The singer was also seen wearing denim on denim in the city over a year later on May 5, 2018. This time she wore a skirt as a top and paired it with distressed jeans and a pink textured jacket and heels.

Rihanna garnered praise and criticism over her Pope-inspired Met Gala look in 2018.

Rihanna wasn’t the only celebrity to take literal inspiration from the Met Gala’s “Heavenly Bodies: Fashion and the Catholic Imagination” theme in 2018, but she had one of the most standout looks of the night. Her interpretation of the Pope’s religious garb included a robe and papal mitre crown.

The encrusted ensemble, created by John Galliano, had jaws dropping because of its intricate embellishment but also because of its taste, with some calling it cultural appropriation.

The businesswoman celebrated with Fenty Beauty in a snakeskin mini dress in Australia in 2018.

More was more for Rihanna’s snakeskin ensemble worn in Sydney, Australia, on October 3, 2018, to celebrate the one year anniversary of Fenty Beauty, the singer’s makeup and skincare line. The mini dress and bucket hat by Atelier Versace perfectly matched her Louboutin heels and Mark Cross purse (not pictured).

She wore a glamorous cage skirt dress to her 5th Annual Diamond Ball in September 2019.

At the 5th Annual Diamond Ball, the singer wore an elegant yet quirky Givenchy velvet dress. The long-sleeve, turtle-neck look was form-fitting until it flared at the bottom with an exposed white cage skirt. She performed later that night at the charity event in the same dress and heels.

The Diamond Ball, created by Rihanna, benefits the Clara Lionel Foundation to “fund groundbreaking, effective climate resilience and justice programs around the world.”

Rihanna wore a blanket-chic look to the 2021 Met Gala.

As one of the last arrivals at the 2021 Met Gala, Rihanna’s look gave a pass for the singer being fashionably late. Rihanna seemed to stray from the theme, “In America: A Lexicon of Fashion,” though. She attended with her partner A$AP Rocky in blanket- and quilt-chic looks.

While A$AP Rocky wore a thrift-store find over his suit, Rihanna wore a Balenciaga blanket-like coat-dress. She paired the dress with a complementary beanie and a crystal headpiece and necklace, getting the best of sleep attire and eveningwear.