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The Boldest and Riskiest Celebrity Fashion Moments of 2025

As 2025 winds down, fashion watchers are taking stock of a year that pushed red-carpet boundaries further than ever before.

While 2024 was widely dubbed the era of “nude dressing,” this year took things a step further, with celebrities embracing sheer fabrics, daring cut-outs and barely-there designs that blurred the line between high fashion and headline-making shock value.

Lottie Moss attended the annual Mon Cheri charity event just weeks ago in this see-through dress
Lottie Moss attended the annual Mon Cheri charity event just weeks ago in this see-through dress

From awards season to fashion weeks across the globe, risky dresses became a defining trend of 2025.

Bra-free silhouettes, strategic transparency and unapologetic confidence dominated events ranging from the Grammys to the Vanity Fair Oscars after-parties.

Bianca Censori was ‘kicked out’ of the Grammys for her naked dress
Bianca Censori was ‘kicked out’ of the Grammys for her naked dress

For many stars, minimal coverage wasn’t just a fashion statement — it was a declaration of individuality and fearlessness.

One of the most talked-about looks of the year came courtesy of Bianca Censori.

Julia Fox’s locks protected her modesty at the Vanity Fair Oscars Party red carpet
Julia Fox’s locks protected her modesty at the Vanity Fair Oscars Party red carpet

Her completely see-through mesh dress at the Grammy Awards instantly went viral, sparking debates about dress codes, artistic expression and celebrity provocation.

Turning away from photographers before dropping her fur coat, Censori’s nude reveal became one of the most controversial red-carpet moments of 2025, cementing her place in fashion history.

Olivia Wilde ditched her bra and flashed her knickers in this Bohemian-style ivory dress
Olivia Wilde ditched her bra and flashed her knickers in this Bohemian-style ivory dress

Julia Fox, no stranger to daring style choices, continued the trend at the Vanity Fair Oscars Party.

Wearing a fully sheer gown that left little to the imagination, the actress once again proved her commitment to bold, conversation-starting fashion.

Megan Thee Stallion left little to the imagination with her nipple covers
Megan Thee Stallion left little to the imagination with her nipple covers

Her look was styled with confidence rather than excess, reinforcing the idea that simplicity can be just as striking as extravagance.

Sydney Sweeney also delivered one of the year’s most memorable fashion moments.

Sydney Sweeney flaunted her ample breasts back in October
Sydney Sweeney flaunted her ample breasts back in October

At Variety’s 2025 Power of Women event, the actress opted for a silver, figure-hugging dress worn without a bra.

The sheer design highlighted her curves while maintaining an air of old-Hollywood elegance, striking a balance between sensuality and sophistication that resonated widely across social media.

Dakota Johnson cheekily flashed her bum and turned heads in this black gown
Dakota Johnson cheekily flashed her bum and turned heads in this black gown

Dakota Johnson’s appearance at the Kering Foundation’s Caring for Women dinner in New York offered another standout moment.

Her see-through lace dress revealed black underwear beneath, and at one point, she cheekily posed with her back to the cameras.

Side boob was on display for Margot Robbie back in September
Side boob was on display for Margot Robbie back in September

The look was daring yet playful, reflecting Johnson’s relaxed confidence and fashion-forward reputation.

Margot Robbie turned heads in London with a shimmering transparent gown that showcased her underwear and featured a daring backless cut.

Halle Berry shocked fans by going knickerless at the Met Gala
Halle Berry shocked fans by going knickerless at the Met Gala

Paired with sleek hair and minimal accessories, the ensemble proved that even the boldest designs can feel polished when styled with intention.

Veteran stars also embraced the trend. Halle Berry stunned at the Met Gala in a black gown with sheer panelling and a plunging neckline, showing that age is no barrier to fearless fashion.

Brooks Nader suffered two wardrobe malfunctions two months ago
Brooks Nader suffered two wardrobe malfunctions two months ago

Meanwhile, Heidi Klum continued her reputation for boundary-pushing looks, stepping out at Paris Fashion Week in a fully transparent white dress that celebrated her confidence and iconic status.

Paris Jackson wore a sheer black off-the-shoulder gown during Stella McCartney’s 2025 Fall/Winter show
Paris Jackson wore a sheer black off-the-shoulder gown during Stella McCartney’s 2025 Fall/Winter show

Elsewhere, Paris Jackson, Zoë Kravitz, Megan Thee Stallion and Maya Jama each delivered their own interpretations of the sheer trend, from mesh cut-outs to feathered skirts and barely-there gowns.

Chrissy Teigen put her bare chest on display in this risky dres
Chrissy Teigen put her bare chest on display in this risky dres

These looks weren’t just about exposure — they reflected a broader shift toward body confidence, self-expression and challenging traditional red-carpet norms.

Maya Jama stunned in a sheer look at London‘s Carbone restaurant
Maya Jama stunned in a sheer look at London‘s Carbone restaurant

As 2025 comes to a close, one thing is clear: risky dresses dominated the fashion conversation.

Heidi Klum’s grillz were not the only thing that got viewers talking with this risky look
Heidi Klum’s grillz were not the only thing that got viewers talking with this risky look

Whether praised for their bold artistry or critiqued for pushing limits too far, these unforgettable looks ensured that this year’s red carpets were anything but boring

Zoe Kravitz’s black dress featured a cheeky peek-a-boo cut-out detailing
Zoe Kravitz’s black dress featured a cheeky peek-a-boo cut-out detailing

— and set the stage for even more daring style moments in the years to come.