16 Best Red Carpet Moments in Hollywood History – Fashion and Drama

Lights, camera, glamour! For decades, red carpet events around the world have set the stage for jaw-dropping fashion and high-voltage drama.

From Hollywood award shows to international film festivals, these star-studded promenades are where icons are born and viral moments unfold.

Fans eagerly await to see their favorite celebrities shine – whether it’s an actress gliding in an elegant gown or an unpredictable stunt that leaves everyone gasping.

Each red carpet moment becomes a piece of pop culture history, replayed and remembered for its style or story.

In this celebratory look-back, we highlight some of the best red carpet moments in history – a mix of iconic fashion statements and unforgettable drama that had the world talking. Each moment features the celebrity who owned it, the event and year, and what made it so iconic or sensational. 

16 Top Red Carpet Moments

Celebrity Event Year What Made It Iconic
Audrey Hepburn Academy Awards (Oscars) 1954 Timeless elegance in a white floral Givenchy gown (Best Actress win)​
Marilyn Monroe JFK’s Birthday Gala 1962 Dazzling nude gown with 2,500 rhinestones, so tight it was sewn on​
Cher Academy Awards (Oscars) 1986 Daring Bob Mackie “Mohawk” outfit with feathers – a rebel statement to the Academy​
Princess Diana Serpentine Gala, London 1994 The “Revenge Dress” – bold off-shoulder LBD defying royal norms on a dramatic night​
Elizabeth Hurley Four Weddings Premiere (UK) 1994 Black Versace dress held by gold safety pins – launched her to instant fame​
Jennifer Lopez (J.Lo) Grammy Awards 2000 Tropical green Versace gown with plunging neckline – so popular it inspired Google Images​
Björk Academy Awards (Oscars) 2001 Whimsical swan dress (with “egg-laying” stunt) – mocked at first, now an internet-loved icon
Britney Spears & Justin Timberlake American Music Awards (AMAs) 2001 Matching head-to-toe denim ensembles – a pop culture couples fashion moment now considered legendary​
Lady Gaga MTV Video Music Awards (VMAs) 2010 The infamous raw meat dress – shocking, conversation-sparking, and utterly unforgettable​
Angelina Jolie Academy Awards (Oscars) 2012 Black gown with thigh-high slit – her right leg pose spawned memes, hashtags, and its own Twitter accounts​
Sacha Baron Cohen Academy Awards (Oscars) 2012 Red carpet prank as “The Dictator” – spilled “Kim Jong-il’s ashes” on Ryan Seacrest’s tux, causing a media frenzy​
Lupita Nyong’o Academy Awards (Oscars) 2014 “Nairobi Blue” Prada gown – a fairytale princess moment the night she won an Oscar, hailed as one of Hollywood’s most significant gowns.
Rihanna Met Gala (“China: Through the Looking Glass”) 2015 Majestic yellow Guo Pei cape gown with a massive train – she literally shut down the Met with this show-stopping look​
Aishwarya Rai Cannes Film Festival 2017 Cinderella moment in an icy blue Michael Cinco ballgown – Bollywood royalty meets Disney princess on the global stage
Billy Porter Academy Awards (Oscars) 2019 Groundbreaking tuxedo-ballgown hybrid – a gender-defying fashion statement praised as art and cementing him as a red carpet icon​
Kim Kardashian Met Gala (“Gilded Glamour”) 2022 Wearing Marilyn Monroe’s original 1962 crystal-covered gown – a jaw-dropping crossover of eras that broke the internet (after losing 16 lbs to fit!)​

1. Audrey Hepburn – 1954 Academy Awards (Oscars)


Audrey Hepburn’s grace and style were epitomized at the 26th Academy Awards in 1954. That night, she arrived in a dainty white floral gown custom-designed by her favorite couturier, Hubert de Givenchy​ according to tribune.com.pk.

The tea-length dress featured a delicate belt and a timeless silhouette that perfectly matched Audrey’s pixie charm. She looked every inch the Hollywood fairy-tale princess – elegant, understated, and radiant. It wasn’t just the dress turning heads; Audrey’s luminous smile and poised demeanor captured hearts as she floated down the red carpet.

This moment became doubly iconic when Audrey won Best Actress for Roman Holiday that very evening.

As she stepped on stage in that beautiful gown, the image was forever etched in Hollywood history. Fashion critics have hailed this look as proof that simplicity can steal the show – the gown’s classic cut and feminine pattern remain influential even today.

More than just a dress, Audrey’s entire presence exuded an effortless glamour that designers still try to emulate. Decades later, her 1954 Oscar look is consistently ranked among the greatest red carpet gowns of all time, a testament to Hepburn’s enduring legacy of style and sophistication.

2. Marilyn Monroe – 1962 JFK Birthday Gala

When you think of show-stopping dresses, Marilyn Monroe’s 1962 “Happy Birthday, Mr. President” gown tops the list. Technically, this wasn’t a film premiere or award show – it was President John F. Kennedy’s birthday gala at Madison Square Garden – but Monroe’s appearance was so legendary that it’s often considered a red carpet moment in its own right.

The blonde bombshell took the stage in a flesh-colored, backless Jean Louis dress sparkling with over 2,500 hand-stitched rhinestones

The design was so form-fitting that Marilyn literally had to be sewn into it moments before her performance.

As Marilyn cooed a sultry “Happy Birthday” to the President in her whispery voice, the audience of 15,000 sat mesmerized.

But it was the dress – often dubbed “the original naked dress” – that truly stole the show. Under the lights, it looked like she was drenched in starlight, the rhinestones giving an almost nude illusion that was scandalously daring for the era.

The gown became an instant piece of pop culture lore: newspapers described Monroe as “breathless” and “bewitching,” and the footage of that moment has been replayed countless times in documentaries. The dress itself went on to break records at auction years later, cementing its status as the most iconic dress of all time

3. Cher – 1986 Oscars (Feathers and Fringe)

@cherdion.tok Jane Fonda introducing Cher at the Oscars 1986🔥 And happy Birthday to the Designer of this and most of Cher’s iconic outfits: Bob Mackie🎉🎂🎁. #cher #icon #janefonda #bobmackie #oscars #oscars1986 #fashion #fashiontiktok ♬ Originalton – Cher Dion


Cher doesn’t just arrive at a red carpet – she makes an entrance. The ultimate proof came at the 58th Academy Awards in 1986, when Cher shocked and delighted onlookers with what can only be described as a Las Vegas showgirl meets high-fashion ensemble.

Designed by her longtime collaborator Bob Mackie, the outfit featured a barely-there black sequined bralette and a low-slung, skin-tight skirt with a daring slit, topped off by a gigantic spiky feathered headdress that resembled a glamorous Mohawk.

The look was bold, bedazzled, and unapologetically over-the-top, embodying Cher’s fearless persona. As she glided down the Oscars red carpet, flashbulbs went wild – had anyone ever seen an “evening gown” quite like this?

Cher later revealed that she intentionally chose this outré outfit to send a message. Feeling snubbed by the Academy’s conservative tastes, she quipped that she “got [her] handbook on how to dress like a serious actress” and then did the exact opposite.

Indeed, the ensemble was a rebellious statement to Hollywood’s establishment, proving Cher would not conform to their norms. The press dubbed it a “1986 Oscars revenge dress” and it has since become part of Oscar folklore.

To this day, Cher’s feathered fantasy remains one of the Oscars’ most iconic fashion moments – a daring display of individuality that expanded the definition of red carpet attire

4. Princess Diana – 1994 Serpentine “Revenge Dress”

Princess Diana wearing the iconic black "Revenge Dress" at the 1994 Serpentine Gallery event
Source: Youtube/Screenshot, Even royalty isn’t immune to red-carpet drama

In June 1994, Princess Diana stepped out at the Serpentine Gallery gala in London and sent shockwaves through the press. Hours earlier, Prince Charles had publicly admitted to an affair – but that night all eyes were on Diana, who arrived looking triumphant in a short, off-the-shoulder black silk dress that would soon be known as the “Revenge Dress.”

The daring cocktail gown by Christina Stambolian broke several royal fashion protocols at once: it was form-fitting, showed plenty of leg and shoulder, and oozed confident sensuality. Diana “broke royal fashion rules” with this outfit, and she did it on perhaps the most emotionally charged evening of her life​

The image of Diana that night is unforgettable: she emerged from her car smiling radiantly, a stunning choker of pearls and sapphires around her neck, as if to say she would not be broken. The press had expected her to skip the event; instead, she turned it into a personal runway.

That sartorial choice – a bold little black dress instead of something somber – was widely interpreted as a sartorial clapback. It showcased her strength and confidence in the face of heartbreak, instantly becoming an emblem of empowerment.

Newspapers around the globe splashed her photo on their front pages, heralding her victory in the “style war.” Decades later, the Revenge Dress remains one of the most iconic global red carpet moments: a perfect convergence of fashion and personal drama that demonstrated how a single outfit can speak volumes.

5. Elizabeth Hurley – 1994 “That Dress” at Four Weddings Premiere

Elizabeth Hurley wearing the iconic black Versace dress at the 1994 premiere of Four Weddings and a Funeral
Source: Youtube/Screenshot, Fashion historians see this as the moment red-carpet fashion matched the importance of the films

Before 1994, Elizabeth “Liz” Hurley was relatively unknown. After 1994, she was the talk of the town – all thanks to one very daring Versace dress. Accompanying then-boyfriend Hugh Grant to the London premiere of Four Weddings and a Funeral, Hurley wore a sultry black Versace gown held together by oversized gold safety pins down the sides.

The plunging front revealed plenty of décolletage, and the cut-outs – strategically pinned – hinted at possible wardrobe malfunction but miraculously stayed intact. The audacious design turned heads instantly.

Photographers couldn’t get enough of the newcomer in “THAT dress,” as it came to be called. In fact, this creation became one of Versace’s most famous gowns ever, right alongside J.Lo’s green Grammy dress​.

What made it iconic? For one, no one had seen anything quite like it on a premiere red carpet. The safety-pin dress walked the perfect line between elegance and shocking sexy.

Media outlets around the world splashed Hurley’s images, and the public was fascinated by the woman in the daring gown. It didn’t just boost her personal profile – it launched her career globally overnight.

Fashion historians often cite this moment as a turning point when red-carpet fashion started becoming as important as the films themselves. Liz Hurley’s safety-pin ensemble remains legendary, copied and parodied countless times.

Even nearly 30 years later, mention “Liz Hurley’s Versace dress” and anyone in fashion will nod knowingly. It’s the dress that took a starlet from obscurity to front-page fame, proving the red carpet’s power to create icons.

6. Jennifer Lopez – 2000 Grammys Green Versace Gown


When Jennifer Lopez arrived at the 42nd Grammy Awards in February 2000, she unknowingly set off a tech revolution – and no, that’s not an exaggeration. J.Lo stepped onto the red carpet in a tropical green Versace gown with a neckline that plunged past her navel, barely secured with brooches.

The sheer, flowy fabric featured a vivid jungle print with splashes of blue and green, and it was sexy, bold, and utterly show-stopping. The audience audibly gasped and cameras went into a frenzy – had anyone ever seen the Grammys this hot?

The dress immediately became one of the most talked-about looks in fashion history, dominating headlines the next day and solidifying J.Lo’s status as a style risk-taker.

So many people around the world rushed to the internet to see pictures of Jennifer’s daring dress that it actually inspired the creation of Google Image Search

Google’s president later explained that there was unprecedented search traffic for J.Lo’s Grammys outfit – users didn’t just want to read about it, they had to see it.

The demand was a catalyst for Google to develop an image search capability. Talk about a culture-defining fashion moment! Beyond its tech legacy, the green Versace gown remains synonymous with J.Lo’s persona: confident, fearless, and glamorous.

She even revisited the look nearly 20 years later on a Versace runway, proving its enduring appeal. This red carpet-moment wasn’t just a dress – it was a worldwide phenomenon that changed the way we use the internet and set the bar for red-carpet sex appeal for years to come​

7. Björk – 2001 Oscars Swan Dress

 

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Leave it to avant-garde Icelandic singer Björk to turn the Academy Awards into her own quirky art performance. At the 2001 Oscars, Björk floated down the red carpet in a now-infamous swan dress – a tulle swan-shaped costume by Marjan Pejoski that wrapped around her neck like a feathery friend.

As if the whimsical white swan (complete with a beak!) draped over her wasn’t memorable enough, Björk playfully “laid” several fake eggs on the red carpet as she posed, adding to the surreality of the moment.

Amid a sea of elegant gowns and tuxedos, here was Björk, delightfully marching to her own beat – or rather, waddling to it.

The reaction was immediate and intense. Some observers were utterly charmed by her originality; others, especially traditional fashion critics, were aghast. One TV style critic famously snarked that it was “probably one of the dumbest things I’ve ever seen”.

For a while, the swan dress was the butt of many jokes and late-night comedy bits. But a funny thing happened over time: that quirky outfit became an iconic piece of pop culture. It’s now celebrated as a symbol of red-carpet risk-taking and individuality.

The dress even has its own dedicated spot in fashion history exhibits. On the internet, Björk’s swan look is often referenced with affection – a beloved meme before memes were a thing​.

In hindsight, Björk turned the red carpet into performance art, reminding everyone that fashion is supposed to be fun. The swan dress may have ruffled some feathers in 2001, but today it’s regarded as a legendary Oscars moment that only Björk could pull off.

8. Britney Spears & Justin Timberlake – 2001 AMAs Denim Duo

Britney Spears and Justin Timberlake wearing matching denim outfits at the 2001 AMAs
Source: Youtube/Screenshot, Britney and Justin’s coordinated denim look has become iconic

The early 2000s were a different time for fashion – and nothing screams 2001 quite like the matching denim formalwear worn by pop power couple Britney Spears and Justin Timberlake.

At the 2001 American Music Awards, the pair arrived coordinated to the max: Britney in a strapless patchwork denim gown with a dramatic studded belt and rhinestone choker, and Justin in a custom denim suit (yes, jean jacket and pants!) complete with a cowboy hat made of denim.

It was a head-to-toe Canadian tuxedo affair, and the cameras absolutely lost it. The world’s biggest pop princess and her NSYNC frontman boyfriend were making a tongue-in-cheek style statement that was as bold as it was adorable.

At the time, the outfits got mixed reviews – some thought it was fashion suicide, while others found it campy and cute. But as years passed, that red carpet moment took on legendary status. It’s now often cited as the quintessential example of early-aughts style and has even been called “the most iconic red carpet outfit ever” in retrospect.

The image of Britney and Justin in coordinated denim has been referenced endlessly in pop culture: from Halloween costumes to magazine shoots, everyone wants a dose of that nostalgic magic.

Why is it so iconic? Perhaps because it captured two mega-stars at the height of teen pop fame, unabashedly having fun with fashion. They weren’t trying to be high-fashion; they were in on the joke, and we all loved it.

This denim duo moment lives on as a feel-good reminder of a more innocent, if stylistically questionable, time. It’s proof that sometimes the most viral red carpet moments come from taking a lighthearted risk and totally owning it.

9. Lady Gaga – 2010 VMAs Meat Dress


By 2010, Lady Gaga was well established as pop’s reigning fashion provocateur – but even so, her appearance at the MTV Video Music Awards that year left the world utterly stunned (and maybe a bit queasy). Gaga arrived wearing the now-infamous “Meat Dress” – a dress, boots, hat, and purse all crafted from real raw meat slabs.

Yes, you read that right: she literally wore an ensemble made of meat. The outrageous outfit, designed by Franc Fernandez, immediately sparked a media frenzy. Under the VMA spotlights, the meat dress looked downright surreal – like something out of a fever dream – and it had everyone talking.

Some praised it as high-concept art and a statement on politics/animal rights, while others were offended or simply confused.

What’s undeniable is that the meat dress became one of the most talked-about red carpet outfits in pop culture history.

It dominated headlines globally the next day. The VMAs have always been a stage for wild fashion, but Gaga managed to eclipse even her own past shockers (this came after a year in which she’d shown up in elaborate Alexander McQueen looks and even a Kermit-the-Frog coat).

When she later accepted an award from Cher while still wearing the meat, handing Cher her meat purse to hold.

10. Angelina Jolie – 2012 Oscars and the Ubiquitous Right Leg

@pplcallmeshai the iconic right leg of angie that launches a million memes #angelinajolie #oscars2012 ♬ original sound – shai💩 – lana del jolie


Sometimes all it takes to make history is a single pose. At the 84th Academy Awards in 2012, Angelina Jolie stepped onto the red carpet in a black velvet Atelier Versace gown with a dramatically high thigh slit – a gorgeous dress on its own.

But what came next turned it into a viral legend: throughout the night, Angelina repeatedly jutted her right leg out through the slit, striking an exaggerated pose with hand on hip, as if to say, “Yes, take it all in.”

The unusual stance caught everyone’s attention. Photos of Angelina’s leg started circulating widely, and by the time the ceremony was over, that limb had taken on a life of its own.

The internet exploded with memes, and someone quickly created a Twitter account for “Angie’s Right Leg” which gained tens of thousands of followers overnight​

The hashtag #AngiesRightLeg trended globally for days. It was all in good fun – people poked fun at how aggressively she flaunted the leg, but also loved it as an emblem of Jolie’s confidence and charisma.

In later interviews, Angelina laughed about how that moment went viral, hinting that there was a “longer story” and that she had chosen that dress last-minute because it was comfortable.

Whatever the behind-the-scenes, what the world remembers is pure meme magic: one of Hollywood’s biggest stars owning the red carpet so hard that even her leg became a celebrity. The pose has since been imitated at parties and photo booths everywhere.

Ultimately, Angelina’s right-leg moment turned a classy fashion choice into a pop culture phenomenon – injecting a dose of humor into Oscar night and showing how one spontaneous moment can overshadow even the awards themselves.

11. Sacha Baron Cohen – 2012 Oscars Red Carpet Prank

Sacha Baron Cohen pranking on the 2012 Oscars red carpet, dressed as General Aladeen with a urn in hand
Source: Youtube/Screenshot, News outlets replayed the clip, and memes of Seacrest looking distressed quickly spread

Red carpet drama isn’t always about fashion – sometimes it’s pure prankster chaos. At the 2012 Oscars, British comedian Sacha Baron Cohen turned up in character as General Aladeen from his film The Dictator, complete with a faux military uniform, sunglasses, and two female “bodyguards.”

In his hands, he carried a fancy urn he claimed contained the ashes of North Korea’s late leader Kim Jong-il (a wild comedic premise in itself). Things took a turn for the outrageous when Sacha, during a live interview with E!’s Ryan Seacrest, suddenly dumped the urn’s contents all over Seacrest’s pristine tuxedo.

For a split second, there was stunned silence – then everyone realized they were witnessing a prank for the ages on Hollywood’s typically genteel carpet.

Seacrest was flabbergasted (trying to maintain his composure while covered in what was presumably pancake mix masquerading as ashes), and security swiftly escorted Baron Cohen away, effectively booting him off the red carpet after the stunt.

The footage went viral within minutes, and it became the watercooler moment of that Oscars. Some found it hilarious – a perfect bit of edgy comic relief – while others thought it was disrespectful to the seriousness of the event.

Either way, it was unforgettable. News outlets around the world replayed the clip, and memes popped up of Seacrest looking forlorn and dusty. The Guardian cheekily noted Sacha was “asked to leave the red carpet” after showering Seacrest in the “ashes”.

In the end, even Seacrest joked about it once he’d cleaned up, and Sacha got priceless publicity for his film. This prank stands out as one of the most outrageous red-carpet dramas ever – proof that at live events, anything can happen.

It brought unpredictable comedy to a usually controlled environment, ensuring that the 2012 Oscars red carpet would be remembered not for a dress, but for a dirty tux and a comedian who dared to surprise Hollywood royalty.

12. Lupita Nyong’o – 2014 Oscars “Nairobi Blue” Gown


Sometimes a red carpet moment is iconic both for fashion and for the emotional weight it carries. In 2014, Lupita Nyong’o had a Cinderella-like breakthrough at the Academy Awards. The Kenyan-Mexican actress was a relative newcomer, nominated for her role in 12 Years a Slave.

She arrived at the Oscars in a breathtaking custom Prada gown in a soft powder blue that she dubbed “Nairobi blue,” inspired by the colors of her hometown in Kenya.

The gown featured a deep V-neck and flowing pleated skirt that swept the floor like a ballgown from a dream. With a delicate gold headband adorning her short hair, Lupita looked ethereal – as if royalty had stepped onto the red carpet.

The look was an immediate hit. Fashion editors praised the dress’s simplicity and its nod to classic Hollywood while still feeling modern and personal. That night became even more poignant when Lupita took home the Oscar for Best Supporting Actress.

As she tearfully declared, “No matter where you’re from, your dreams are valid,” her princess-worthy dress seemed the perfect embodiment of that fairytale moment. The gown landed on every best-dressed list and was later regarded as one of the most significant gowns in Hollywood history.

It wasn’t just beautiful; it symbolized a new star being born. Lupita twirled on the red carpet and during the Vanity Fair after-party, the skirt billowing around her, creating picture-perfect images that magazines still reprint years later. In one night, she cemented her status as a fashion icon.

This moment stands out not only for the exquisite dress and Lupita’s radiant beauty but for the emotional resonance of seeing a talented newcomer live out her dream in real time. The “Nairobi blue” Prada gown will forever be associated with joy, representation, and the magic of a well-deserved win.

13. Rihanna – 2015 Met Gala “Yellow Princess” Train

Rihanna wearing a stunning yellow gown with an elaborate train at the 2015 Met Gala
Source: Youtube/Screenshot, Rihanna resembled an empress or a high-fashion princess

If there’s one modern celebrity who consistently owns every red carpet, it’s Rihanna – and her crowning fashion moment has to be the 2015 Met Gala. The theme was “China: Through the Looking Glass,” and Rihanna arrived fashionably late in a look that quite literally stopped the show.

She wore an opulent imperial-inspired cape gown by Chinese designer Guo Pei, in a striking shade of canary yellow. This was no ordinary gown – it featured a massive circular train, lined with lush fur trim and covered in intricate gold embroidery, that extended so far behind her that it required several assistants to carry (and nearly took up the entire staircase)​.

As she ascended the famous Met steps, photographers scrambled to capture the full grandeur. From above, the train spread out like a gigantic flower or, as the internet humorously noted, an omelet – sparking countless memes comparing her gown to delicious cuisine.

Yet the overriding reaction was awe. Rihanna looked like an empress or a high-fashion fairy-tale princess. The sheer drama of the ensemble set a new standard for the Met Gala. Fashion journalists hailed it as a masterpiece: a perfect blend of theme, artistry, and star power.

Rihanna’s confident demeanor – she owned that look, beaming and posing regally – turned what could have been a costume into an iconic moment. The gown instantly became one of the most memorable red carpet-looks ever.

The Guardian later noted that the extravagant train and embroidery made Rihanna look “like a true queen,” applauding her dramatic entrance and fearless style​

In the years since, the yellow gown has appeared in museum exhibits and coffee-table books, symbolizing the pinnacle of red carpet fashion. This was more than just a dress; it was a cultural event. Rihanna proved that taking a risk on couture could result in a red carpet victory so grand that it’s seared into collective memory – sunny side up and fabulous.

14. Aishwarya Rai – 2017 Cannes Cinderella Moment

The Cannes Film Festival red carpet is renowned for its high glamour, and in 2017, Aishwarya Rai Bachchan delivered a moment of pure magic on those iconic steps. Often hailed as one of Bollywood’s most beautiful actresses (and a former Miss World), Aishwarya has a history of stunning Cannes appearances, but this was something special.

She arrived for the Okja premiere in a voluminous ice-blue ball gown by Michael Cinco, looking every inch like Cinderella at the ball.

The off-shoulder gown featured a massive, billowing skirt with yards upon yards of fabric, embellished with sparkling beads and silver embroidery that glittered in the Riviera twilight. As Aishwarya twirled and posed, the dress fanned out around her in a perfect circle – a photographer’s dream.

Crowds and paparazzi alike gasped at the sight. There was a global star channeling a Disney princess moment on an international stage, and it was breathtaking. The gown’s hue matched the evening sky and its silhouette was straight out of a fairy tale.

Social media went wild with admiration, and images of Aishwarya’s look trended worldwide. Fashion outlets from Teen Vogue to Harper’s Bazaar gushed that she “wowed on the Cannes red carpet” in a princess-style couture creation.

Many noted that at 43 years old, a mother of one, Aishwarya was confidently redefining what princess glamour could be – showing that grace and beauty have no age limit. This moment also had a significant cross-cultural impact: it brought a touch of Bollywood grandeur to the Western-dominated fashion conversation, underlining Cannes as a truly global platform.

The “real-life Cinderella” headlines poured in, and that powder-blue gown secured its place in red carpet history. Years later, fans still refer to this look as one of Cannes’ all-time greatest. It was a fairy tale come to life, proving that the magic of red carpet fashion knows no borders.

15. Billy Porter – 2019 Oscars Tuxedo Gown


In 2019, actor Billy Porter transformed the Oscars red carpet into a platform for fearless self-expression. Porter arrived in what can only be described as a jaw-dropping tuxedo-ballgown hybrid.

From the waist up, he sported a perfectly tailored traditional black tuxedo jacket and bow tie; from the waist down, it blossomed into a voluminous velvet evening gown skirt that swept the floor. This custom creation by designer Christian Siriano was elegant, dramatic, and unlike anything men typically wear to the Oscars.

Porter’s entrance sent photographers into a frenzy and left fellow attendees cheering – he quite literally shut down the red carpet with that look.

More than just a fashion statement, Porter’s outfit carried powerful symbolism. In a single ensemble, he blurred the gender lines of formal attire, making a bold statement about inclusivity and self-expression.

“When you come to the Oscars, you must dress up,” Porter quipped – and dress up he certainly did. The gown-tux was meticulously crafted (sharp shoulders and lapels juxtaposed with the graceful skirt), and it fit Porter’s personality to a tee: theatrical, confident, and groundbreaking.

Fashion journalists and fans alike raved; it was “widely highlighted for its elegant design” and immediately cemented Porter as a modern fashion icon.

Critics hailed it as one of the best Oscars looks ever, praising it as a piece of “political art” that started conversations about masculinity and dress codes.

Indeed, Porter noted he simply wanted to celebrate all facets of himself and prompt people to think – and he succeeded. The impact was clear as the photo went viral: here was a celebration of freedom in fashion, applauded by designers and even academics for its significance.

After this moment, more men in Hollywood began experimenting with bold red-carpet styles, citing Porter as inspiration. His 2019 tuxedo gown will forever be remembered as a game-changer – a triumphant and glamorous moment that expanded the possibilities of what a red carpet “dress” could mean.

16. Kim Kardashian – 2022 Met Gala “Marilyn Moment”

 

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How do you top a red carpet repertoire that already includes breaking the internet with selfies? If you’re Kim Kardashian, you time-travel to borrow the most famous dress in Hollywood history.

At the 2022 Met Gala, with the theme “Gilded Glamour,” Kim stunned everyone by showing up in Marilyn Monroe’s actual 1962 dress – yes, the very same crystal-studded nude gown that Marilyn wore to sing “Happy Birthday” to JFK (mentioned earlier in this list). It was a crossover of eras that sent pop culture aficionados into a frenzy.

The dress, a true museum piece designed by Jean Louis, is covered in thousands of hand-sewn rhinestones and famously had to be sewn onto Monroe.

To fit into the fragile garment, Kim reportedly underwent a strict diet and lost 16 pounds in three weeks

As Kim stepped onto the Met carpet with boyfriend Pete Davidson at her side, the flashbulbs went wild. For a moment, it felt like Marilyn was there again – Kim had styled her hair in a platinum blonde updo to channel Monroe’s look.

The effect was pure old-school Hollywood glamour, blended with modern star power. Attendees literally stopped in their tracks to catch a glimpse.

Social media exploded: Kim Kardashian wearing Marilyn’s dress?! It felt like a surreal pop culture loop. The moment was not without controversy – conservators fretted about the delicate dress (Kim only wore it for the carpet and changed immediately after) and there was debate about whether this was appropriate.

But beyond the chatter, the visual was undeniably iconic. It was as if two of the biggest icons of their respective eras had converged. The sheer audacity and spectacle of it made headlines worldwide.

Kim’s Marilyn moment encapsulated what the Met Gala is about: fashion meets fantasy meets celebrity. Here was a reality star-turned-mogul paying homage to a screen legend in the most literal way possible.

And in doing so, she created a new piece of pop culture history. The image of Kim in the sparkling nude illusion gown instantly went viral, ensuring that the legacy of Marilyn’s dress found a whole new generation of admirers. Love or hate the idea, this was one for the ages – a red carpet moment that was glamorous, dramatic, and deeply symbolic of Hollywood’s enduring allure.

Bottom Line

Red carpet events aren’t just about fashion—they’re about unforgettable storytelling, cultural impact, and moments that define generations. From timeless elegance to rebellious statements, each celebrity who graces the carpet leaves behind a narrative woven in style, confidence, and drama.

These iconic appearances transcend mere gowns and tuxedos, capturing the heart of pop culture and inspiring countless dreams, memes, and conversations worldwide. Ultimately, the red carpet reminds us that glamour isn’t only about what you wear; it’s how boldly and authentically you wear it.