We’re nearing the tail-end of award season, with the big show – the Oscars – happening later this month. With that lead-up comes lots of retrospectives about the nominees’ best looks of their career (and occasionally some good-natured ribbing about their first stylist-free looks). While major awards shows can definitely be worth reminiscing about, we wanted to check out some of Hollywood’s biggest stars today and the looks that made us sit up and take notice of them.
From red carpets at the Emmys, Golden Globes and Academy Awards to smaller events like film premieres or the MTV Video Music Awards, these 20 celebs have had the opportunity to step out in countless couture creations and designer duds. They might have plenty of memorable looks in their repertoire (indeed, for some it was difficult to narrow things down), but these are the ones that stand out as being emblematic of when they either made it big or began their career as the next major superstar.
Sure, some might have been household names before, but are there any looks that are as ubiquitous as these outfits? And, more importantly, could anyone have rocked them as well? We think not!
20 Olivia Wilde Was Bridal Goals
We might have already known Olivia Wilde thanks to her role as the bartender Alex on The O.C., but we really noticed her as Thirteen on House – and then she walked the red carpet in this bridal-style Reem Acra gown to the 2008 Emmys and everyone took notice.
The dress was the stuff of wedding dreams, thanks to its flattering fit and the sparkling detail that was limited to the cap sleeves. On the small screen, we had only seen Wilde in tomboyish looks, usually with crazy hair. In this gown, she showed us that she belonged among the Hollywood elite – and consumers thought so, too. Sales went through the roof for this gown once Wilde was seen in it.
19 Gwyneth Paltrow In Ralph Lauren
With her Hollywood pedigree roots (father is the late director Bruce Paltrow, mom is actress Blythe Danner), it wasn’t like we didn’t know who Gwyneth Paltrow was, but this was the dress that really put her on the map – it even has its own Wikipedia entry!
Paltrow was nominated for Best Actress at the 1999 Oscars for her role in Shakespeare in Love when she wore this pink Ralph Lauren creation. At the time, many said that she looked like Grace Kelly, and the actress was credited with bringing pink back into fashion, as the look was copied afterwards. Largely regarded as one of the greatest dresses ever worn on the red carpet, we can safely say this was Paltrow becoming a bonafide superstar.
18 Julia Roberts In Vintage Valentino
Everyone remembers how often Leonardo DiCaprio was nominated – and lost – before finally getting his big win, but back in 2001, Julia Roberts was already on her third nomination when she finally scored the award for the titular role in Erin Brockovich.
Sure, Roberts was America’s Sweetheart, and one of the biggest actresses of our time, but has any look she’s worn been as memorable as this vintage black-and-white Valentino, complete with retro updo? It was a monumental night for the actress’s career, and arguably the apex of it, as she had never been so relevant before or since. And, if we’re being honest, a lot of that is owed to this very dress!
17 Cate Blanchett’s Embroidered Back
Cate Blanchett is now considered a style icon, able to rock modern silhouettes, geometric shapes, sleek columns and an array of colours with almost no effort. In 1999 at the Academy Awards (she was nominated for Elizabeth), she embarked on her career as a style trendsetter thanks to this bespoke creation by John Galliano, which she herself helped to design!
The focus was all on the back of the dress, thanks to a sheer back that featured delicately embroidered flowers and a hummingbird. It is without question that, almost at the beginning of her career, this gown put her on the fashion map.
16 Kate Hudson In Custom Versace
Another actress who comes from Hollywood royalty, Kate Hudson is the spitting image of her mother, actress Goldie Hawn, but she truly came into her own thanks to this custom Versace dress.
Hudson first began making a name for herself with her role as Penny Lane in the film Almost Famous. Here, for the 2002 Golden Globes – which she attended to celebrate the movie’s nominations – Hudson proved that she could accept her newfound stardom with grace and some serious style chops.
Blending California cool with Hollywood glam, the dress was perfect for the actress, and soon saw her becoming a fixture at worthy events.
15 Bjork’s Swan Dress
Not all memorable dresses are good dresses. Case in point: Bjork. Would any of us even know the Icelandic singer’s name were it not for the infamous swan dress? Probably not, which is why she deserves a spot on this list!
The iconic dress was worn to the 2001 Oscars and was widely criticized and discussed for weeks afterwards for being outlandish and OTT. In the years since, it’s been parodied by comedians, in films and even in children’s TV shows! You could even argue that the dress has become more famous than the woman who wore it!
14 Marion Cotillard’s Mermaid Scales
Could a regular person ever wear a dress that appeared to be made of fish scales, with two strange rosette shapes on the bust? We doubt it. Could gorgeous French actress Marion Cotillard wear it when she was winning Best Actress for playing Edith Piaf in La Vie En Rose, rock it and have everyone say it was a style revelation? Weirdly, yes!
Opting for iconic French designer Jean Paul Gaultier, Cotillard wore the gown in 2008, when she was the first actress since 1972 to win a Golden Globe for a foreign-speaking performance. It was one of our first introductions to Cotillard and, while the dress divided critics, it certainly cemented her spot in the Hollywood upper echelons.
13 Nicole Kidman In Chartreuse Couture
Yes, Nicole Kidman had been acting since the 1980s and yes, she had been married to mega-star Tom Cruise, but this look was what really made her a movie star.
Considered one of the most influential red carpet gowns in fashion history, Kidman showed off her statuesque silhouette in this chartreuse silk Dior from designer John Galliano at the 1997 Oscars. Not only did this dress make people sit up and take notice that Kidman was more than the wife of Tom Cruise, but it also gave some major cred to Galliano! It has since been considered the first “true” couture gown on the red carpet, as Vanity Fair reports.
12 Reese Witherspoon’s Reinvention
Reese Witherspoon had been acting in various teen flicks or lower-budget productions in the 1990s. She married her Cruel Intentions co-star Ryan Phillippe and had two children at a fairly young age but, by 2007, the couple had split and Witherspoon decided to take the Golden Globes as an opportunity to reinvent herself, giving single girls everywhere major breakup goals.
Now an Oscar winner thanks to Walk the Line, Witherspoon showed up in a slim-cut golden Nina Ricci mini dress and hot bangs, and made it arguably the best look she’s ever had.
11 Blake Lively’s 'Red' Carpet Arrival
A relatively new face on the red carpet, Blake Lively clearly learned some tricks thanks to the fashion focus on her hit show Gossip Girl, because when she showed up rocking this major red Versace gown to the 2009 Emmys, she made it clear that she had arrived.
With its plunging neckline and her perfect hair, Lively was clearly moving from the small screen to the silver screen. Prior to this look, most people who had heard of the actress were teens who enjoyed the soapy TV show or had watched Sisterhood of the Traveling Pants. After this look, though, there was no doubt that she was going to be one to watch.
10 Beyoncé Got Golden
All right, yes, Beyoncé was a famous face years before she wore this gown, thanks to her success with Destiny’s Child and as a solo artist. We had seen her rock matching outfits designed by her mother, Tina Knowles, and we knew that she was pretty bodacious, thanks to the staggering success of 2003’s Crazy in Love.
However, this 2007 golden Elie Saab gown was what cemented her status as a movie star. Worn at the Golden Globes, Beyoncé was nominated for her role in Dreamgirls, both as an actress and for Original Song. We might have already known that she was a triple threat, but seeing her all glammed up in something that didn’t match her co-stars? Perfection.
9 Zendaya’s Locs
The youngest celebrity to make it on this list, it also happens to be the most recent. Zendaya, a singer-actress with roots in the Disney Channel universe, basically reinvented herself as a fully-fledged grown woman when she was just 18 years old in 2015 – and it wasn’t just the dress.
In addition to looking more mature but still age-appropriate in the white Vivienne Westwood dress, it was the teen’s locs that got people talking, thanks to the insensitive comments spouted on Fashion Police. Zendaya, always a class act, responded with such eloquence that the look – and the actress herself – have since been immortalized in Barbie form. We’d say that’s definitely being put on the map!
8 Hilary Swank’s Low Back
Hilary Swank, thanks to tough award-winning roles in films like Boys Don’t Cry and Million Dollar Baby, didn’t really have a reputation in Hollywood for being ultra-feminine. That totally changed in 2006 when she walked the red carpet at the Academy Awards in a navy blue backless Guy Laroche dress that was the visual definition of “business in the front, party in the back.”
The weeks of training paid off big time because there hasn’t been a dress before or since that was as memorable as this one on Swank. It’s an added bonus that it’s further immortalized as being the second Oscar win for Swan, too!
7 Scarlett Johansson In Valentino
Scarlett Johansson had been around for a while, thanks to beginning her career as a child actor, and, by the time she walked the Golden Globes red carpet in this fiery Valentino tank dress in 2006, she was on her fourth nomination for the statuette in a row! Clearly, people knew who she was, but this dress was described by Bustle as “the dress that defined 2006.” We’d say that qualifies at putting a star front and center!
As one of the more curvy actresses of the decade, Johansson’s silhouette was celebrated in this design which showed that the indie actress had blossomed into a fully-fledged woman.
6 Keira Knightley In Aubergine
Keira Knightley began getting buzz after appearing in 2002’s Bend It Like Beckham in full tomboy mode. A year later, she was in 1800s finery with the first installment of Pirates of the Caribbean, but by 2006, she had secured her spot as a fashionista, something that has carried over into numerous endorsements for major fashion houses like Chanel and Asprey.
2006 was her year, though, and she showed it when walking the red carpet to the year’s Oscars in this aubergine taffeta gown from Vera Wang. Nominated for Best Actress for playing Elizabeth Bennett in the acclaimed Pride and Prejudice, it was her first nom at the awards – but not her last!
5 Lady Gaga’s Meat Dress
Anyone who has been following Lady Gaga knows that, from the outset of her career, she dressed pretty wildly. Avant-garde get-ups and theatrical makeup contributed to the bulk of her wardrobe.
But let’s take it back to 2010, shall we, when Gaga wore the outfit that has arguably become her most famous ever! The “Meat Dress” was constructed from raw flank steak with matching meat boots and what could be called a fascinator. When asked about her controversial outfit by Ellen DeGeneres, Good Housekeeping reports her as saying, “If we don’t stand up for what we believe in…we’re going to have as much rights as the meat on our own bones.” She added, “And I am not a piece of meat.”
4 Elizabeth Hurley In Safety Pins
For Elizabeth Hurley, there were two clear divisions of her career in the 1990s: B.T.D. (Before The Dress) and A.T.D. (After The Dress). Prior to donning this look in 1994, Hurley was only really known for being actor Hugh Grant’s girlfriend.
When she showed up to the premiere of Four Weddings and a Funeral rocking this Versace dress, she got everyone buzzing and made fashion history.
In an interview with Harper’s Bazaar, Hurley was pretty modest about the whole thing, saying, “I’m delighted a dress I wore might be something someone would think about, but it wasn’t really that big a deal to me at the time.”
3 Halle Berry In Sheer Burgundy
Halle Berry is ageless. Since the 1990s until now, she has stunned on and off the red carpet with gorgeous styling, a fabulous figure and a chic hairstyle. Seriously, does anyone rock a pixie cut as well as the Oscar winner?
However, it was this dress that got the most people talking and cemented Berry’s spot in history as the first black woman to win an Academy Award for Best Actress for 2002’s Monster’s Ball. The Elie Saab creation was both classic and trendy, thanks to a sheer bodice covered by an intricate array of flowers across the bust and a full burgundy skirt.
2 Michelle Williams In Canary Yellow
It’s weird to think of a time when Michelle Williams wasn’t nailing it on the big screen, back when she was just a girl on Dawson’s Creek. One look at her in this canary yellow gown – an almost impossible shade to master – and it’s like she was born to be a star.
With then-husband, the late Heath Ledger, at the 2006 Academy Awards, the sunny Vera Wang dress coupled with a romantic updo and red lip made Williams top most of the Best Dressed lists and show the world that she was more than a TV character – she was someone who could take creative and fashion risks.
1 Jennifer Lawrence Was A Vision In Red
For some, Jennifer Lawrence’s most memorable dress might have been the Dior confection she wore when she won Best Actress, tripping over her skirts on her way up to the podium. To them, we raise this red Calvin Klein tank dress, which ushered Lawrence onto the international stage as the hottest new thing to hit Hollywood.
This was the first Oscars dress for the actress and we don’t think we’re exaggerating when we say she absolutely nailed it! The simple gown put the then-20-year-old (nominated for Winter’s Bone – her first of four noms) on the map and on everyone’s radar.