Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

Celebrities took daring fashion risks in 2023, pushing boundaries with avant-garde dresses and eccentric headpieces Rihanna, Cardi B, Harry Styles, and more made the boldest style statements Discover the fearless fashion choices that captivated the world

2023 saw some of the most daring fashion moments in Hollywood history. One standout moment came in January when Doja Cat turned heads at the Schiaparelli show during Paris Fashion Week by arriving covered in red body paint and tiny beaded crystals.

Several months later, Rihanna turned heads at the May Met Gala with her stunning appearance on the red carpet, dressed in a striking white Valentino gown. The gown featured oversized 3D floral detailing and a dramatic hood, with the floral portion transforming into a shawl that elegantly draped over the singer's shoulders.

Not to be outdone, men also brought their own unique style to the forefront. Billy Porter, for example, made a bold statement at the Golden Globes in January by donning a dramatic red velvet gown. He added a surprising touch to the look by pairing it with a white shirt and bow tie, showcasing his daring and unconventional fashion sense.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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The Fiercest Fashion Risk Takers of 2023: Rihanna, Cardi B, Harry Styles and More

2023 saw some of the most daring fashion moments in Hollywood history. Doja Cat kicked off the year with a bold statement at the Schiaparelli show during Paris Fashion Week, appearing covered in red body paint and tiny beaded crystals, setting the tone for wild and wacky outfits to come.

A couple of months later, Rihanna made a stunning appearance at the Met Gala in May, dazzling on the red carpet in an eye-catching white hooded Valentino gown adorned with oversized 3D floral detailing. The dress captivated attention as the floral portion seamlessly transformed into a flowing shawl that elegantly draped over the singer’s shoulders.

It wasn't just women who embraced bold fashion choices. Billy Porter, for example, broke barriers by donning a striking velvet red gown at the Golden Globes in January, paired with a white shirt and bow tie for an unexpected and edgy twist.

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Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Doja Cat

At the Schiaparelli show during Paris Fashion Week in January, the singer made a daring statement by appearing in head-to-toe red body paint and crystals. She complemented her newly-painted skin with a strapless red mini dress, red leather boots, and a flowing red shawl.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Billy Porter

At the Golden Globes held in January in Los Angeles, Porter made a striking appearance in a red velvet dress. The dress boasted a double-breasted blazer-like silhouette at the top, then flared out at the waist and flowed into pleats at the bottom. To complete the look, he paired it with a white button-down shirt and a red bowtie.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Harry Styles

At the Brit Awards in London in February, the Watermelon Sugar singer showcased a playful twist on the timeless suit. He donned a striking black velvet blazer with a dramatic flare at the waist, paired with matching black flared velvet trousers. The standout element was the oversized floral detailing on the collar Styles sported.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Jenna Ortega

The actress embraced the essence of Wednesday Adams at the Met Gala in New York City in May. Ortega donned a striking black gothic asymmetrical dress designed by Thom Brown, complete with a lace-up corset top, an ultra-cropped tweed blazer, a tiered skirt, and a flowing train. The ensemble was adorned with numerous bows, paired with knee-high socks, and finished with black and white heeled brogues.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Rihanna

Rihanna made a statement with her attire at the Met Gala in New York City in May. She appeared in a striking white hooded Valentino gown with extravagant floral embellishments. The gown later transformed into a sleek white strappy dress, while the floral-adorned hood converted into a fashionable shawl.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Julia Fox

At the Cannes Film Festival in May, Fox stunned in a striking white gothic see-through dress designed by Nicolas Jebran. The avant-garde dress was made of a plastic-like material and featured a dramatic thigh-high slit, tied into a giant knot on her left shoulder before flowing out into a train. To complete the look, Fox wore white face paint and dark blue lipstick.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Viola Davis

In France at the Cannes Film Festival in May, the actress stunned in a stunning Valentino couture ensemble. Davis radiated as she flaunted a grand fluffy feathered white and silver shawl, which she gracefully wore over an exquisite white one-shouldered gown.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Helen Mirren

At the Cannes Film Festival in May, the actress turned heads in France with her bold choice of bright blue hair paired with a stunning blue floor-length gown by Del Core. The dress boasted long sleeves, a plunging neckline, and ruching at the waist.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Cardi B

The rapper turned heads with her choice of attire at the Gaurav Gupta haute couture show during Paris Fashion Week in July, donning a striking lime green dress paired with a matching puffy hooded shawl. The ensemble was adorned with vibrant green sequin detailing, creating a bold and memorable look.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Demi Lovato

The singer made a bold fashion statement at the MTV Music Video Awards in New Jersey in September, donning an exaggerated silhouette. She sported an oversized black leather coat with sharp, angular shoulders, pairing it with a black mini dress and black heels.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Nicki Minaj

At the September MTV Video Music Awards in New Jersey, the rapper showcased her unique take on the Barbiecore trend. Minaj donned a stunning baby pink Dolce & Gabbana corset bodysuit paired with a flowing long pink sheer skirt. She completed the look with a matching pink veil featuring delicate lace detailing on the rim.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Saweetie

At the September MTV Video Music Awards in New Jersey, the rapper stunned in a stunning floor-length pink sequin dress from AREA’s fall/winter 2023 collection. The unique dress showcased side cut-outs and was adorned with two light pink bones — one on her collar, and the other on her waist.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Lil Nas X

At the September MTV Video Music Awards in New Jersey, the singer made a statement by donning a stunning white dress from Palomo Spain. The dress boasted elegant long lace sleeves, a daring thigh slit, and intricate ruched detailing. To complete the look, he added a white feather headpiece and paired it with chunky white boots.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Jodie Turner-Smith

The actress and model made a bold fashion statement at Vogue World in London in September, donning a pair of black underwear and a dramatic oversized bow that wrapped around the upper half of her body. She completed the daring ensemble with long black gloves and strappy black heels.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Sienna Miller

Miller confidently flaunted her pregnancy bump with elegance at Vogue World in London in September. She donned a chic cream two-piece ensemble by Schiaparelli, consisting of a cropped shirt with intricate ruche detailing and a flowing skirt that beautifully highlighted her belly. Completing the look with black sheer tights and elegant black heels.

Bold Fashion Gamblers: Rihanna, Cardi B, Harry Styles, and Beyond

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Anne Hathaway

Anne Hathaway made a daring fashion choice at the CFDA Awards in New York City in November, stepping out in a head-to-toe denim ensemble. The actress sported a dark blue and white denim corset top, paired with a tie-dye effect blue and white denim skirt that cascaded to the floor and flared out to the side.