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A Look Back at the Biggest Golden Globes Fashion Risks of All Time
By SAMANTHA SCHNURR
FEB 28, 2021

The Golden Globes would not be complete without style.
As award season officially begins once again on Sunday, Feb. 28, anticipation is mounting over the fashion viewers will see as the star-studded show unfolds. However, while dressing to the nines in designer looks has become synonymous with the glitzy annual show, given the ongoing coronavirus pandemic, attending award ceremonies has taken on a new form over the past year. With nominees set to accept the awards virtually, stars and their stylists are striking a balance between putting together a look for the milestone moment while also staying aware of the digital format and current events.
“For me, it’s more important to be mindful of the tone of what we’re putting out there and be conscious of the fact that people are facing real struggles,” stylist Avo Yermagyan told The Hollywood Reporter during a roundtable interview. “Although we want to give them beautiful moments and escapism, we still want to make sure that we’re sensitive to what the world is going through.”
Simultaneously, there are some styling benefits to these unprecedented circumstances. “It’s a different way of working,” stylist Sophie Lopez told THR of styling clients for this virtual world. “We are able to cheat in ways that we couldn’t if it was an in-person event…We can safety pin things, we don’t have to worry about people tripping over their hemlines.”
PHOTOS: Golden Globes 2021: See Nominees at Their First Show
Still, one thing remains exactly the same: secrecy. While this year’s Golden Globe looks remain confidential until the big night, thanks to nearly eight decades of Golden Globe fashion to reflect on, fans have an idea of what makes a Golden Globe look—style, glamour and more frequently, boldness.
While couture gowns and tailored tuxedos have become a standard of the occasion, as the years go on, some celebrities continue to push the sartorial boundaries of the big night in new and unexpected ways. From one-of-a-kind prints and eccentric silhouettes to over-the-top accessories and unconventional inspirations, the Golden Globes red carpet has seen many fashion risks—and we’d bet there are plenty more in store this year and in the years to come.
Now, as we count down the final hours before the 2021 ceremony, take a walk down memory lane and revisit all of the carpet’s riskiest looks below!

The Nanny nominee rocked florals in an unexpected way at the 1996 Golden Globes: on her head.

In the last year of the 1990s, the There’s Something About Mary nominee boldly hit the red carpet in a floor-length floral wrap layered over pants.

In 1980, the triple threat was a winner rocking some one-of-a-kind print.

In 1996, the Melrose Place nominee channeled some daring glamour in the form of this metallic gown with a slit spanning most of the dress.

Back in 1987, Jane Seymour brought plenty of moons to the star-studded night courtesy of her standout dress print.

The actress stood out from the crowd at the 2014 golden Globes in this Stéphane Rolland design featuring head-to-toe sculptural ruffles.

The actress appeared to draw inspiration from the 1920s with her sequined halter dress at the 2004 Golden Globes. She accessorized the sheer, backless design with a beaded headband.

While you more frequently see tie-dye on T-shirts, that didn’t stop the actress from attending the 2012 Golden globes in a voluminous Monique Lhuillier dress in a similar eye-catching print.

With its nude illusion bodice, mermaid tail, and cut-out shoulders, there was a lot to the actress’s 2009 Golden Globes Carolina Herrera look.

Never one to adhere to fashion rules, the star boldly stepped out in a colorful pair of mismatched shoes at the 2011 Golden Globes. Her floral Vivienne Westwood gown with tulle detailing was just as attention-grabbing as her quirky footwear.

Lara Flynn Boyle
The actress made a gutsy move by donning a ballerina-style dress complete with a flouncy tutu at the 2003 award show. Her lace-up heels completed the unforgettable red carpet look.