Fashion is timely, while style is timeless - and celebrities are often masters at both.
Whether it's the best Oscars looks of all time or the best Met Gala jewellery looks, celebrities can inspire trends and offer inspiration on how to recreate similar styles.
But every now and then, a star steps out from the status quo to try a new look, one which might take a few years to really catch on. From trying a divisive trend to wearing something daring for the time, these celebrities offered up looks that were ahead of their time.
Classic red carpet looks that were ahead of their time
Cindy Crawford, 1991
What happens when one of the world’s most famous supermodels at the peak of her career dates one of the most in-demand actors at the time? Pure, glamorous magic. Cindy Crawford accompanied her then-boyfriend, Richard Gere, to the 1991 Oscars in a Versace gown so ahead of its time, it has its own Wikipedia page.
Cindy’s Versace dress, with straps and a plunging neckline in a fiery hot red, brought fashion to the Academy Awards in a way that wasn’t typical for the early 90s. Now, with the parade of red carpet looks, it’s all about the fashion, but a few decades ago, it was more conservative. Cindy brought glam and upped the stakes like never before.
Barbra Streisand, 1969
A multi-talented icon, Barbra Streisand is one of the rare celebrities to have EGOT status – meaning she won an Emmy, a Grammy, an Oscar and a Tony. And it was back in 1969, when she was to collect her Oscar for her work in Funny Girl, that Barbra wore one of her most forward-thinking outfits ever. Shunning a more typical gown for a sequined pantsuit by Arnold Scaasi, complete with flared legs and tuxedo cuffs, Barbra’s look was a fun, feminine ensemble with touches of menswear and all-out glamour.
The fact the ensemble was a touch see-through – another daring and ahead-of-its-time touch – was purely an accident.
"That night, in my dressing room, I was choosing between two different outfits," Barbra has previously told W magazine. "One was lovely, but very conservative. And then there was the pantsuit with plastic sequins. I had no idea that when the lights hit that outfit, it would become transparent!"
Gwyneth Paltrow, 1996
Proving her fashion acumen back in 1996, Gwyneth Paltrow wore what would become of her all-time best looks. The Oscar winning star of Shakespeare in Love rocked up in a fresh-off-the-runway ruby-coloured suit velvet suit designed by Tom Ford for Gucci.
It was a merging of fashion and Hollywood that wasn’t necessarily ‘done’ at the time. Gwyneth – looking louche and relaxed but still sexy and empowered - offered a masterclass in androgynous chic.
Rihanna, 2015
When Rihanna arrived on the Grammy’s Red Carpet in 2015, her look divided fans and critics. The oversized, multi-layered tulle gown by Giambattista Valli was an explosion of pink – a candyfloss dream. In the years that followed, big tulle gowns became something of a trend.
Julia Roberts, 1991
Back when red carpets were a more casual affair, Julia Roberts found the perfect way of looking stylish while still dressing down.
The Pretty Woman icon chose an effortlessly cool pinstriped suit comprised of a long, double-breasted blazer with shoulder pads (opting to wear nothing underneath, for a youthful, fresh feel), a matching mini skirt and sheer black tights.
Sharon Stone, 1998
It was a case of serendipity and resourcefulness that led to one of the most memorable Oscars looks of all time – and a masterclass in high-low dressing. Before the 1998 Oscars, Sharon Stone was left without a dress, causing the Basic Instinct star to improvise.
Mixing a stunning, silk Valentino skirt with a crisp white shirt, the outfit became one of the most talked about.
Madonna, 1995
Pretty much everything Madonna has done has been ahead of its time, breaking down boundaries on matters such as sexuality, fashion, and ageing since the 80s.
For the 1995 MTV VMAs, what appears to be a relatively simple red carpet look for Madonna, was actually an ingenious fashion decision that solidified her credentials. Perhaps anticipating the eventual dominance of Tom Ford, she recreated a head-to-toe look from his 1995 Gucci catwalk.
Madonna wore the same electric-blue silk Gucci shirt and trousers with a matching Gucci monogram bra underneath, originally worn by Kate Moss on the runway. It helped make runway fashion more accessible and seem more wearable, putting a spotlight on the designer like never before.
Kate Moss, 1995
A masterclass in minimalist dressing, Kate Moss still looked every inch the supermodel in a simple, black suit for the 1995 VH1 Fashion and Music Awards. Proof that an impactful fashion moment doesn’t need to try too hard, and an argument for every woman adding a well-tailored, timeless suit to her capsule wardrobe.
Angelina Jolie, 2012
Angelina Jolie stole the spotlight at the 2012 Academy Awards thanks to a gorgeous Versace dress – and one of her legs. The black, strapless velvet dress was surprisingly traditional, except for a thigh-high slit that became an iconic moment thanks to Angelina’s expert posing. Choosing one signature flash of flesh was a subtly sexy twist, and definitely ahead of its time.
Marilyn Monroe's 1962 dress (as seen on Kim Kardashian)
Marilyn Monroe is – still – one of the most famous icons in history. Her trademark looks, her film roles and her fashion have made her a legend, and it was the dress she wore in 1962 that proves how ahead of her time she was. While fashion was typically more reserved back then, Marilyn was sewn into a sequinned, daring gown that matched her skin tone, giving her a shockingly progressive nude illusion.
She wore the gown to sing happy birthday to President John F. Kennedy. Today, ‘naked’ dresses and sheer numbers are a popular choice, and Marilyn’s exact dress was so ahead of its time it looked perfectly modern when worn by Kim Kardashian for the 2022 Met Gala.
Nicole Kidman, 2007
Considered one of Nicole Kidman’s best-ever looks, she proved how ahead of her time she was when it came to memorable, bold fashion choices with her 2007 Oscars dress. Wearing Balenciaga – she’d later become an ambassador for the brand in 2024 – Nicole chose a ravishing red dress with a structured bow design at the neck and a flowing train.
From the avant-garde structural design to the vibrant colour against her fair skin, it was a striking moment of all-out fashion.
Julia Roberts, 2001
When Julia Roberts attended the 2001 Oscars – the year she picked up an award for her work in Erin Brockovich – she opted for a stunning black and white Valentino gown. Simple and understated, it wasn’t the design itself that made her look a forward-thinking choice, but the fact that it was a rare example of vintage on the red carpet.
In the early 2000s, it was more expected for stars to go all out with a new creation, but Julia opted to bring a touch of timelessness with this 1992 archival dress. Now, it’s not unusual for archival looks and vintage outfits to be seen all over the red carpet.
Katharine Hepburn
While not a red carpet look, Katharine Hepburn’s whole career was pretty much ahead of its time thanks to the style she committed to. Considered shocking for the time, Katharine was notorious for always choosing to wear tailored trousers or wide-legged pants with a simple button-up shirt.
While today it may be a capsule wardrobe staple, it was practically unheard of at the time, especially for a woman in Hollywood.
Charlotte Gainsbourg, 2007
Her mother was Jane Birkin, a fashion icon who had the iconic bag named in her honour, so it wasn’t surprising that actress and singer Charlotte Gainsbourg proved an innate sense of style at the 2007 Met Gala.
Wearing something that would look just as trendy today, the actress wore a multi-patterned, layered Balenciaga dress, styled by Nicolas Ghesquiere.
Madonna, 1984
Ahead of its time in both committing to a bit for a pop star’s latest album cycle and bringing a sense of drama and theatre to the awards shows, Madonna reinvented the MTV Video Music Awards when she frolicked all around the stage in the now iconic repurposed wedding dress. Inspiring imitators for decades, Madonna made fashion – and pop culture – history.
Sarah Jessica Parker, 2000
An unusual style for SJP, the Sex and the City fashion icon wore a divisive pinstripe look from Vivienne Westwood for the 2000 Screen Actors Guild Awards. With the wide, almost oversized trousers, SJP’s style was ahead of its time – and the creative twist on the corseted, long-sleeved waistcoat added a high-fashion twist.
Celine Dion, 1999
Celine Dion’s best looks over the years have proven that the singer always hits the right notes when it comes to her style. But in 1999, she wore what would become one of the most divisive – and memorable – Oscars looks of all time.
A slouchy, oversized white silk suit (courtesy of John Galliano) worn back-to-front (and with a matching oversized fedora), Celine was universally panned. However, with time, this look was just ahead of its time. With the backwards jacket, she offered a classy take on sexy dressing, with a backless moment for the ages.
Rosemarie Stack, 1967
American model and occasional actress Rosemarie Stack was an early advocate for taking big risks at prestigious events like the Academy Awards. Wearing a head-to-toe striped print, Rosemarie’s look in the late 60s would still be a standout moment on the red carpet today.
Audrey Hepburn, 1968
Audrey Hepburn’s Givenchy dress she wore to the 1968 Oscars was elegant, refined and ahead of its time. With the modern flair of encrusted sequins and floral designs, an empire waist and a subtle cutout around the midriff, Audrey looked classic while somehow very contemporary.
Dolly Parton, 1977
Dolly Parton has always done her own thing – and it’s why she’s one of the celebrities who has mastered a signature look. And that commitment to doing things differently means that plenty of her throwback looks feel refreshingly ahead of their time. Take her pink cowgirl look to the 1977 Grammys. Playful western wear has now been seen on everyone from Jennifer Lopez to Beyoncé, and Dolly was out there doing it first.
Princess Diana, 1994
Dubbed the Revenge Dress, Princess Diana wore this stunning, off-the-shoulder gown designed by Christina Stambolian to an event in London in 1994, planned for the same day the now King Charles publicly admitted to infidelity during their marriage.
With a daring amount of cleavage on show, plus a short hemline, it was the first time a member of the Royal Family had been so forward-thinking and adventurous with their fashion.
Demi Moore, 1989
The ubiquity of athleisure has made items like bike shorts and leggings just as welcome on a red carpet as they are in the gym these days, but Demi Moore was an early advocate for the style back in 1989.
The star of Ghost shocked everyone when she rocked up on the Oscars red carpet – famously a place full of Hollywood glamour – in a hybrid dress/bodysuit that she fashioned herself out of spandex bike shorts, a corset, and a metallic floral-print fabric.
Julia Roberts, 1990
Unlike other times we’ve seen Julia Roberts embrace menswear silhouettes, this one was just straight-up menswear. With an oversized look in the jacket and trousers, Julia’s look might have been questionable at the time, but is a very modern trend.
Rihanna, 2023
For the 2023 Oscars, Rihanna took a very forward-thinking stance on dressing while pregnant. Embracing maternity with modernity, the Grammy-winning pop icon showcased her growing bump in a black sheer dress, with patches of black leather completing the edgy look.
Cher, 2000
Never one to play by the rules, Cher’s daring fashion sense has guaranteed she’s always been ahead of her time with trends. Rocking the red carpet in 2000, Cher showed up in double denim. This was once considered one of the ultimate fashion faux pas but has since become a very classic style worn by some of the chicest names in showbiz. Cher must’ve known.
Kate Hudson, 1998
For the 1998 MTV Music Awards, How to Lose a Guy in 10 Days star Kate Hudson opted for a mesh/see-through two-piece. Simple but still sexy and stylish, the red carpet looked fresh and modern and would still look on trend today.
Nicole Kidman, 1997
In the docuseries, In Vogue: The 90s, Gwyneth Paltrow summed up how the Oscars were in the 1990s. Dubbing them “restrained” and suggesting people felt they had to dress more conservatively to be taken seriously, Nicole Kidman would come along and shake it all up.
The always glamorous screen star brought haute couture to the Oscars in a now iconic chartreuse beaded Dior dress. The documentary – available to watch on platforms including Disney+ and Hulu - also reveals Nicole wore the gown “against the advice of her team” because fashion wasn’t considered serious. But Nicole - ahead of her time – helped spotlight the art and extravagance of fashion.
Lady Gaga, 2019
Lady Gaga is known for some of her daring, avant-garde looks (meat dress, anyone?), so her 2019 Golden Globes gown was surprisingly restrained for her.
Wearing a voluminous Valentino Haute Couture blue dress with accent sleeves, Gaga’s special touch included dyeing her hair to match the outfit, a very forward-thinking twist on accessorising for the Red Carpet.
Tracee Ellis Ross, 2018
A form-fitting, head-to-toe metallic jumpsuit is not the easiest thing for anyone to pull off, so props to actress Tracee Ellis Ross for this fun and inspired look.
The star of Girlfriends and Black-ish wore this forward-thinking Balmain jumpsuit to the W Magazine party.
The Golden Globes Red Carpet, 2018
Making a political statement and using their power to amplify the voices of women? It was both ahead of their time and, as many people would agree, a long time coming. For the Golden Globes in 2018, the women of Hollywood united to make a statement regarding the #MeToo movement.
Kim Kardashian, 2013
She was compared to everything from Mrs Doubtfire to a couch when she wore this floral Givenchy dress to the Met Gala. However, as controversial as this might be, the look didn’t deserve much of the hate. With its bold, almost head-to-toe print and matching opera gloves sewn into the silhouette, the Riccardo Tisci-designed gown is incredibly high fashion and memorable.
Jennifer Lopez, 2000
This isn’t any dress, this is *the* dress - and one of JLo's best-ever looks.
Images of JLo in the sheer, flowing tropical printed dress were downloaded from the Grammy website 642,917 times in just 24 hours after she arrived on the red carpet wearing the now iconic Versace look. It's even the reason Google created the Google Image search.
It was an unapologetic and dynamic take on red carpet dressing that pushed the boundaries and changed red carpet fashion forever.
