The Most Stunning Red Carpet Look, Every Year Since 1999

What have the most stunning red carpet looks every year since 1999 been? For fashion enthusiasts, nothing quite beats watching the stars strut the red carpet. According to CNN, the tradition dates back to 1922, when the rug was used at the very first Hollywood premiere. As Amy Henderson, a historian at the national Portrait Gallery in Washington explained, "the idea of glamour became instantly associated [with it]." 

Soon, the red carpet became the standard for premieres around the world. By the '60s, the walk down the iconic carpet was televised, and fans got to glimpse their favorite stars. As Henderson describes them, stars became "perfected creatures that somehow walk the planet. We can mimic what they wear in makeup or how they dress, but we can't really be them because they're different."

It's true — we do love examining every detail of what the celebs wear on the red carpet. And who can blame us? Some fashions on the red carpet these days are nothing short of works of art. And we've certainly seen some outrageous, unforgettable looks on the red carpet over the years. Here are our picks for the very best fashions from every year since 1999.

In 1999, most red carpet fashions featured streamlined, simple silhouettes. So when Gwyneth Paltrow turned up to the Oscars in a full-skirted, baby pink gown fit for a princess, she caused quite a stir. The elegant gown was designed by Ralph Lauren, and according to Time, it's gone down in history as one of the best Oscar outfits ever. Apparently, it even started a trend of bubblegum pink dresses for the rest of the year. In fact, the dress was still making waves 20 years later in 2019, when model Karen Nelson donned the very same dress for an InStyle photo shoot.

However, even though many critics couldn't get enough of Paltrow's pink princess look, others were less impressed. As CR noted, some people thought the dress was outdated, immature, or even ill-fitting. Whether you loved or hated this gown, it's definitely gone down in history as one of the most famous dresses ever to grace the red carpet.

With the new millennium came new fashions; whether you loved the somewhat bizarre fashions of the early 2000s or not, you have to admit that the era delivered some unforgettable red carpet looks. Our favorite has to be the slinky, all-white gown and boa combo that Britney Spears wore to the Grammy Awards in 2000.

As Fashionista noted, this red carpet look is definitely one of the most iconic in fashion history. The dress by Randolph Duke oozed modern style and sophistication, white the eye-catching white fur stole by Oscar de la Renta added some timeless glamour to the look. As far as we're concerned, the outfit was the perfect mixture of old and new fashion — perfect for seeing in the New Year.

It's clear that this particular look has withstood the test of time. In 2020, 20 years after the outfit first made its appearance, Lizzo appeared at the Grammy Awards in a strikingly similar white dress with a white stole. As Versace, Lizzo's designer, pointed out on Instagram, the look was an homage to the classic Spears look — even though Lizzo added a few contemporary touches.

While we always love an understated, classic, elegant look, sometimes a big, bold statement outfit is right up our street. So when it comes to the fashions of 2001, we have to choose Björk's outrageous swan gown as the best red carpet look. 

As CR pointed out, absolutely everyone was talking about this Marian Pejoski dress. With the feathered tutu skirt and the literal swan neck and head wrapping around the neck, this creation looked more like a stuffed animal than a gown. As Björk later said of the dress, "I was very aware when I went to the Awards that it would probably be my first and last time. So I thought my input should really be about fertility, and I thought I'd bring some eggs." And yes, the singer did bring literal eggs, which she tried to "lay" as she walked down the red carpet.

While the iconic outfit wasn't "serious" according to Björk, it inspired plenty of swan dresses from other fashion designers in years to come. In 2014, for instance, the dress was recreated by Valentino for the label's opera-inspired collection.

In 2002, everyone was talking about Halle Berry's breathtaking Elie Saab gown. With its sheer bodice covered with delicate floral embroidery and its deep red draped silk skirt, this unforgettable red carpet look quickly shot Berry to the top of most best dressed lists. As Hello! reported, Berry also made a stir at the Oscars that year by becoming the first woman of color to win the award for Best Actress.

These days, Elie Saab is a well-known designer brand; however, at the time, Saab was far less prominent. In fact, the designer once said, "Halle Berry made the name Elie Saab more popular... she managed to really put the name Elie Saab on the international market. [She's] the reason my brand took off" (via CR).

A version of the legendary dress was eventually sold at auction by Barneby's, who reported that it was deemed the eighth best Oscar gown of all time.

In 2003, Kate Hudson brought some funky, boho chic fashion to the Golden Globes in an eye-catching, strapless gown by Valentino. With its asymmetrical, multi-print paneled skirt, the dress was a complete departure from the old-school Hollywood glamour that was once the red carpet staple. In fact, Hudson's outfit looked more like something you'd throw on to stroll along the beach.

 As Valentino told InStyle, "When she wore my gown she left the world, including me, in awe with her young, relaxed and elegantly fresh California look." The dress defied convention and boldly trumpeted in a new era of modern, boho looks.

For Hudson, the famous look was an opportunity for her to feel a little more like herself on the red carpet. As she once said, "I'm a hippie at heart. I wear the clothes, and they're the best. And the music is incredible, too" (via Glamour).

Nicole Kidman's fascinating, ice blue gown for the 2004 Oscars is definitely one of the most memorable red carpet looks of all time. The Chanel gown, made by Karl Lagerfeld, featured a strapless mermaid silhouette with a tulle tasseled tail and a matching neckline; the star paired the gown with delicate Christian Louboutin heels. Apparently, the dress took over 400 hours to make (via Oscar). 

That same year, Kidman was named the face of Chanel's iconic No. 5 perfume, as noted by the Independent. As the actress later told The New York Times Magazine, her decision to become the face of the perfume was partly "because I wanted to go and have Karl Lagerfeld dress me and run around." Sounds like her Oscar outfit was just one of the perks of the job!

Kidman's outfit was also named one of the best 100 Oscar dresses of all time by Vogue, and it's easy to see why. This effortless, elegant, red carpet look was the perfect sophisticated sleek meets delicate feminine mix.

In 2005, Charlize Theron wowed fashion enthusiasts when she stepped out in a luscious, baby blue gown at the Oscars. The John Galliano for Christian Dior creation featured a strapless, fitted bodice, and a dramatic ruffled skirt with a four foot long train (via PopSugar). Theron paired the dress with delicate Bulgari jewellery (via Vogue). The red carpet look was definitely eye-catching!

Theron has actually been seen in Dior dozens of times. In 2004, she became the face of the brand's J'adore perfume, so it's easy to see why she chose to wear Dior the following year at the Oscars. For Theron, the brand perfectly encapsulates her notions of glamour and femininity. As she explained to Grazia, "We as women can dress up, wear make-up, go out and not have to sacrifice our independence, power, or voice. You can be feminine, independent and strong all at once." In this particular gown, we have to agree — she was a total force!

One of our favorite red carpet looks of 2006 has to be Diane Kruger's white Elie Saab number at the Oscars. The fitted, strapless gown featured horizontal panels of lace, ruffles, and embroidery, and was yet another example of Kruger's ever-flawless style. As The Telegraph noted, Kruger paired the lovely dress with delicate accessories and a tousled hair style to avoid looking too bridal.

A 2006 article in The New York Times explained how it was a big year for Saab, who was well on his way to establishing himself as a prominent luxe designer. Apparently, Kruger's show-stopping gown at the Oscars came just one day after a successful ready-to-wear show in Paris. The Times described Kruger's gown as a "sugar-spun confection, with its lacy tiered wedding-cake ruffles and mermaid train." Indeed, it was at this moment that Saab demonstrated his mastery of "big event" dresses.

Bright, bold colors are always something of a risk on the red carpet. However, at the 2007 Cannes Film Festival, Angelina Jolie bravely showed that a pop of color is sometimes the best way to steal the show. The actress wore a blindingly bright yellow satin gown by Ungaro complete with a twisted wraparound bodice, adding a little texture to the otherwise simplistic look. Jolie paired the dress with Chopard yellow diamond earrings to look like a literal ray of sunshine (via The Hollywood Reporter).

As W noted in 2016, a decade later, the bright yellow gown would have been right at home on the red carpet as 2016 was all about bright yellows. Luckily, Jolie's risky color choice paid off — and Cannes was the perfect place for such a bold look. As the Los Angeles Times noted, Cannes is the perfect place to experiment with fashion; as designer Setefano Gabbana said, "The dress code is more relaxed, and the celebrities have the chance to be more daring." And as the Times put it, Jolie's bold dress "uplifted critics and fans alike."

The French are known for their style — and at the 2008 Oscars, Marion Cotillard gave us all an unforgettable example of French chicness. As Vogue pointed out, the glamorous actress not only took home the Oscar for Best Actress, she also won plenty of approval for her Jean Paul Gaultier gown. The stunning dress complimented its mermaid silhouette with a scale-like white and gold scalloped pattern. As Reuters noted, Cotillard's gown stood out from the crowd, as many chose to wear  red gowns to the ceremony that year.

At the time, the New York Post noted that the dress caused a lot of buzz. "She has a real presence and personality, an ease within a sense of propriety," fashion editor Laird Borrelli-Persson said. And Jelka Music, who helped with Cotillard's fitting, said, "She has a really good eye... In couture, the dress was known as 'The Mermaid Queen.' It is maybe the most mermaid dress ever." 

This red carpet look definitely set the gold standard for mermaid dresses, so as far as we're concerned, it's the obvious choice for best dress of 2008.

In 2009, Frieda Pinto both embraced and defied classic red carpet styles with her intriguing, royal blue gown by John Galliano. It was her first year at the ceremony, and she certainly didn't disappoint when it came to fashion. The sparkly dress featured one lace sleeve, intricate sequin embroidery, and a floaty tulle skirt. At the time, the gown got a shoutout from The Times, who reported that Pinto also donned a 100-year-old antique ring from India.

This unique, memorable gown has gone down in red carpet history. As Moira Macdonald, arts critic for The Seattle Times, wrote in 2020, the dress is one of her "all-time Oscar favorites." She explained, "I love the asymmetry, the whimsical sleeve, the sequins, the flakiness of the skirt, and above all, that perfect shade of blue, like a summer sky just after sunset." We have to say, that pretty much sums up this dreamy dress.

In many ways, Kate Hudson's gown for the 2010 SAG Awards epitomized contemporary red carpet glamour; the actress chose a bright white, form-fitted gown by Emilio Pucci. While the front of the dress was clean and simple, with long sleeves and a high square neckline, the backless cut along with a sheer sequined panel on one of side of the dress gave it a surprising touch of glamour (via Elle). The red carpet look was both understated and completely riveting. According to JustJared, Hudson elegantly paired the statuesque gown with over $1 million worth of Cartier jewelry, including a tassel necklace worn on her back, a Roger Vivier clutch, and Versace shoes.

At the time, Hudson's outfit topped multiple best dressed lists, including lists by Entertainment Weekly, Harper's Bazaar, and Vogue. Back then, this look was clearly a winner — and as far as we're concerned, it still holds up to this day.

Natalie Portman's sweet, romantic look at the 2011 Golden Globes stole many critics' hearts and it's not hard to see why. The actress wore a sleeveless Viktor & Rolf gown in blush pink satin. With a red rose at the center of the neckline, the dress gathered around the bust then cascaded effortlessly to the floor.

Designers Viktor and Rolf spoke to Vogue at the time about designing the iconic couture gown specifically for Portman. "After seeing her performance in Black Swan," they explained, "we were deeply moved and inspired by her range as an actress." 

Viktor & Rolf's red carpet creation became an instant classic, perhaps because it seemed to suit Portman so well. As Viktor and Rolf explained, they designed it with her unique qualities in mind. "She is the embodiment of a powerful woman: as talented as she is stunning," they proclaimed.

For her appearance at the 2012 Oscars, Emma Stone chose a decidedly bold look; once you've seen the dress, you'll probably never forget it. The dramatic Giambattista Valli Louis gown in bright fuchsia featured a gathered waist, and most memorably, a gigantic bow on the side of the high neckline. As The Telegraph described it, the dress made Stone look like a "beautiful present."

As the Daily Mail noted, the dress was strikingly similar to a gown worn by Nicole Kidman at the 2007 Oscars. Nevertheless, Stone's red carpet look still stood out. At the time, critics were divided; the Daily Beast called the ensemble "regal and glamorous," while the New York Daily News reportedly put Stone on their worst dressed list, noting, "Looks like this Giambattista Valli Louis red bow is wearing an Emma Stone!" 

Even though Stone's brave red carpet hit wasn't a universal success at the time, we certainly won't be forgetting it any time soon!

Who can forget this fairy princess look from Jennifer Lawrence at the 2013 Oscars? When Lawrence arrived at the ceremony in a breathtaking, baby pink strapless gown by Christian Dior, it was hard to ignore the actress. The structured gown featured a fitted bodice and a voluminous skirt. At the time, HuffPost noted that the look was a real departure from J-Law's previous red carpet fashion, which in the past had consisted of darker colors.

One reason that you probably remember this gown is that its massive skirt caused Lawrence to trip as she walked up the steps to the stage to accept the award for Best Actress. As she later said, "What went through my mind? A bad word. That starts with 'F,'" (via Vogue). Fair enough!

Regardless of her awkward fall, the dress has definitely gone down in history as one of the best ever Oscar outfits.

In our book, nothing beats a romantic gown dripping in delicate embroidery. To that end, in 2014, Cate Blanchett stole the show at the Oscars with a stunning Armani Prive gown. The gold dress featured sheer cap sleeves, a crinoline-lined flared tulle skirt and, most notably, Swarovski crystal sequins embroidered across the entire dress. As Giorgio Armani told The Hollywood Reporter earlier that year, "I've always appreciated how she pushed the fashion envelope." And this lavish gown certainly did just that!

Not only did Blanchett's gown steal all of the attention at the Oscars, it also cost the most. As Vogue reported at the time, the gown apparently cost $100,000! And that's just the start, as Blanchett's jewelry was said to be worth roughly $18 million! We honestly can't even imagine spending that much on a red carpet look — but for Blanchett, this expensive outfit definitely paid off!

After years of experimental panels, asymmetrical hemlines, and unusual artistic designs, actress Felicity Jones went back to basics with her gown at the SAG Awards in 2015 — and the effect was nothing short of breathtaking. Jones wore a classic, simple, pale peach colored gown by Balenciaga. With a straight elegant fit, the main feature of the dress was the structured criss cross paneled shoulders, which gave the dress a '50s feel (via The Hollywood Reporter).

As Bustle noted at the time, Jones' look was "totally regal." The actress reportedly paired the gown with vintage pearl and diamond jewels to complete the sophisticated red carpet look. And according to the Los Angeles Times, Jones' seemingly simplistic hairstyle wasn't as easy as it looked. Alex Polillo, her hairstylist, explained that the do took a whole lot of de-frizzing product, along with a technique involving a toothbrush to ensure the actress's baby hairs stayed in place. Wow, clearly it takes time and effort to look this good.

You probably wouldn't think that latex would be a go-to material for a red carpet gown. However, in 2016, Beyoncé, the queen herself, proved us wrong. The superstar showed up at the Met Gala in a nude Givenchy dress made entirely of latex. According to Vogue, the specific material was Talalay latex, which is frequently used in mattresses — doesn't exactly sound like haute couture. However, the dress was laced with pearls and was apparently worth around $8,000.

Whether you loved it or hated it, the unusual red carpet look certainly got people talking. According to "the Baroness," one of the designers behind the gown, latex was still very new to the fashion industry at the time. She told Vice, "I'm the reason why latex clothing exists in America." She went on to explain that initially, latex clothing was hyper sexualized. However, over the years, it's become more popular.

When it came to putting on Beyoncé's latex number, there were a number of issues — apparently, during the fitting process, Beyoncé's body even had to be lubricated!

Beyoncé isn't the only one in the Knowles family to wow on the red carpet. In 2017, just one year after Beyoncé's latex gown made headlines, Solange made waves with a remarkable gold outfit by Gucci at the Grammy Awards. As Essence reported, the singer completely stole the show with her pleated gown, complete with fanned shoulder pieces and peplum waist. According to Allure, the star paired the metallic dress with a pair of Lady Grey Concentric hoop earrings. This was one red carpet look that you just couldn't take your eyes off.

The daring custom design definitely got people talking. PopSugar described Solange as a "golden goddess," Harper's Bazaar and Vogue named her one of the best dressed artists at the event, InStyle gave her an honorable mention, and The Cut noted that her statuesque look was particularly on theme, since she won her first Grammy Award that evening.

As HuffPost noted, the stunning Armani Prive gown worn by Allison Williams at the 2018 Oscars became instant bridal inspiration. The stunning nude dress featured cap sleeves, a fitted bodice covered in crystals, and a flowing full skirt. With her soft old-school waves, Williams looked like a true Hollywood princess for her first ever appearance at the Oscars. The red carpet look instantly sent her to the top of the best dressed lists.

According to USA Today, Williams was one of the first stars of the evening to walk on the red carpet. With her diamond earrings and matching bracelet, Williams looked every bit the Hollywood starlet.

For Williams, the evening at the Oscars really was a dream come true. It was her first appearance at the event, and, as she wrote on Instagram at the time, it had been her dream since childhood. It's lovely to see her looking so breathtaking on such a special day!

Incredible fashions on the red carpet shouldn't be reserved for women. In 2019, singer Harry Styles proved the point by wowing us all with a bespoke Guggi suit featuring a sheer arm and chest panel, a flamboyant neck ruffle, and lace cuffs. As Styles' fashion coordinator Harry Lambert explained to Vogue, a lot of thought went into the show-stopping look. "I think everyone was expecting Harry to be in sequins, bright colors and a crown, but we decided on a different type of 'camp' that hopefully would surprise," Lambert explained. This suit, Lambert went on, was all about rethinking "traditionally feminine elements" into more a masculine outfit. "The look, I feel, is elegant. It's camp, but still Harry."

Alessandro Michele, Gucci's creative director, was closely involved in designing the outfit. Styles, Lambert, and Michele sat down together with a mood board and narrowed down their choices. "Harry and myself went through all the fabrics, sketches and ideas and shared our favorites," Lambert recalled. "From there, Gucci produced samples of these and fittings commenced." Sounds like this collaborative process was pretty painstaking — but it was definitely worth it!

At the start of a new decade, pop sensation Janelle Monáe brought some futuristic fashion vibes to the red carpet at the Grammy Awards. The star opted for a super dramatic silver gown, complete with a hood, long sleeves, an open back, and a large A-line floor-length skirt. 

What made this look so remarkable were the crystals — 168,000 of them to be precise. As Booth Moore reported on Twitter, the star's dress was absolutely dripping with Swarovski crystals. Apparently, the unbelievable gown took over 600 hours of hand sewing to complete. To add even more sparkle to the look, Monáe also wore a crystal choker and a sparkling set of rings.

As Monáe told Billy Porter on the red carpet after he compared her to old-school Hollywood film star Grace Kelly, "I knew I had to come and show up." And show up she certainly did — it would be hard to beat this jaw-dropping outfit!