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Runway rewind: 25 biggest fashion moments of the 21st century (so far)

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Runway rewind: 25 biggest fashion moments of the 21st century (so far)

As we step into 2025, celebrating the quarter mark of the 21st century, the fashion landscape’s transformative evolution is worth noting. The past 25 years have witnessed a kaleidoscope of trends, pioneering designers, and some of the biggest fashion moments that have redefined style and culture. 

From Lady Gaga’s meat dress at the 2010 VMAs, which catapulted fashion into the stratosphere of performance art, to Pharrell Williams’ Vivienne Westwood hat at the 2014 Grammys, which spawned a thousand memes and solidified the singer’s status as a fashion icon — the 21st century has been a wild ride for fashion lovers. 

Meanwhile, designers like Alexander McQueen, John Galliano and Virgil Abloh have consistently pushed the envelope, challenging perceptions of beauty, identity and creativity. As we celebrate this milestone year, let’s look at the 25 biggest fashion moments of the 21st century — the moments that made us gasp, inspired us and altered the fabric of fashion.

25 of the most iconic fashion moments of the 21st century, ranked

1. Lady Gaga’s meat dress — 2010 

Lady Gaga has given fans one too many iconic fashion moments in her two-decade-long career. However, her meat dress, designed by Franc Fernandez for the 2010 MTV Video Music Awards, remains the biggest fashion moment in the 21st century.

The bold, beef-based ensemble — which included a raw meat hat, shoes, and purse was more than just a shocking stunt; Gaga used the dress as a powerful statement protesting the US military’s “Don’t Ask, Don’t Tell” policy, which prevented service members from disclosing their sexual identity. By wearing the meat dress, Lady Gaga aimed to highlight the issue of people being treated like pieces of meat, stripped of their individuality and autonomy. 

The dress has since become an iconic symbol of Gaga’s commitment to self-expression and artistic experimentation, cementing its place in fashion history as a daring moment.

2. Alexander McQueen’s iconic Armadillo shoes — 2010

Lady Gaga wore the Armadillo shoes in her song Bad Romance (Image: Courtesy of IMDb/Lady Gaga: Bad Romance)

Alexander McQueen’s Armadillo shoes, which debuted in his Spring/Summer 2010 runway show, Plato’s Atlantis, are a fine example of the late designer’s creative genius. These 10-inch, claw-like stilettos, with their armoured, reptilian design, not only redefined the boundaries of footwear but also embodied McQueen’s fascination with the relationship between nature and technology. 

The shoes’ intricate, hand-crafted details and imposing silhouette made them an instant sensation, with fashion mavens like Lady Gaga (who borrowed it for her Bad Romance video and was later gifted the pairs by her then-fiancé Taylor Kinney) and Daphne Guinness embracing the design. As a symbol of McQueen’s unbridled creativity and enduring influence on the fashion world, the Armadillo shoes remain an iconic, awe-inspiring, and unforgettable fashion moment of the 21st century.

3. Kim Kardashian wearing Marilyn Monroe’s “Happy Birthday, Mr. President” dress— 2022

Left: Marilyn Monroe; Right: Kim Kardashian (Image: Courtesy of Instagram/@kimkardashian/Kim Kardashian)

Mega-celebrity Kim Kardashian’s appearance at Met Gala 2022, wearing Marilyn Monroe’s iconic “Happy Birthday, Mr. President” dress, was a fashion moment that sparked both awe and controversy. 

The custom-made, Jean Louis-designed gown, which Monroe famously wore to serenade President John F. Kennedy in 1962, was loaned to Kardashian by Ripley’s Believe It or Not! museum. By wearing this historically significant dress, Kardashian not only paid homage to Monroe’s legacy but also ignited a global conversation about celebrity culture and the preservation of cultural heritage. However, the Kardashian was later accused of damaging Monroe’s iconic dress.

4. Coperni’s viral spray-on dress on Bella Hadid — 2022 

Image: Courtesy of Instagram/@coperni/Coperni

French brand Coperni’s Spring/Summer 2023 show finale at the Paris Fashion Week 2022 will be etched in fashion history as one of the most unforgettable moments of the 21st century. In a futuristic gesture, designers Sébastien Meyer and Arnaud Vaillant orchestrated a live, on-runway transformation, where a team of technicians sprayed a liquid fabric onto supermodel Bella Hadid’s body, moulding it into a stunning, bespoke dress.

This show-stopping, minutes-long process not only showcased the brand’s innovative approach to fashion but also highlighted the possibilities of technology-driven textile design. As the dress took shape, the audience witnessed a true fashion revolution, blurring the lines between art and style.

5. Jennifer Lopez’s iconic green Versace dress — 2000

Right at the beginning of the 21st century, singing sensation Jennifer Lopez gave fans a jaw-dropping fashion moment with the green Versace gown she wore to the 42nd Grammy Awards. The dress’s daring jungle-print design and plunging neckline made it an instant sensation, with the internet buzzing to see more.

According to Project Syndicate, the dress’s massive popularity is often credited with inspiring the creation of Google Images, as users desperately searched for pictures of Lopez in the stunning gown. 

Nearly two decades later, Lopez reprised the look, wearing a reimagined version of the dress during her Versace runway debut in 2019. Yes, the one where she strutted like a true queen! This nostalgic nod cemented the dress’s status as a timeless piece.

6. The futuristic fashion influence of The Matrix — Early 2000s

biggest fashion moments
Keanu Reeves and Carrie-Anne Moss in a still from The Matrix (1999)

Wachowskis’ The Matrix (1999) and its futuristic, dystopian aesthetic had an indelible impact on fashion, with its influence still felt today. The film’s costume designer, Kym Barrett, created a distinctive look that blended functionalism with high-fashion flair, epitomised by Neo’s (Keanu Reeves) sleek, all-black leather outfit and Trinity’s (Carrie-Anne Moss) iconic, micro-shaded sunglasses.

These skinny, futuristic shades, paired with the characters’ streamlined, monochromatic ensembles, helped define the early 2000s fashion landscape, with several designers incorporating similar elements into their collections. 

7. Britney Spears and Justin Timberlake’s matching denim outfits — 2001

Britney Spears and Justin Timberlake’s coordinated denim outfits, which they famously wore to the 2001 American Music Awards, remain one of the most iconic fashion moments in pop culture history. The matching, head-to-toe ensembles, featuring Spears in a denim dress and Timberlake in a denim suit, were a bold, cheeky nod to the casual, all-American charm of the early 2000s.

While the looks may have been ridiculed by some at the time, they have since become a retro-futuristic time capsule, symbolising the carefree, pop-cultural zeitgeist of the era. 

8. Paris Hilton’s 21st birthday chainmail dress — 2002

OG influencer Paris Hilton has been cultural reset for a reason. Her dazzling, silver, barely-there chainmail dress, worn to celebrate her 21st birthday in 2002, is an indelible image of the era’s flashy, party-girl aesthetic. Designed by Julien Macdonald, the daring, sequined gown showcased Hilton’s carefree, attention-grabbing persona, cementing her status as a budding socialite and tabloid fixture. As a cultural snapshot of the early 2000s’ excess and extravagance, Hilton’s iconic birthday dress continues to evoke nostalgia and fascination, symbolising the fleeting, glittering allure of celebrity culture.

Recreating the look, Hilton wore a version of her iconic chainmail birthday dress as she performed “Stars Are Blind” alongside Miley Cyrus and Sia at the second annual Miley’s New Year’s Eve Party on 31 December 2022.

9. Marc Jacobs’ bold, Comme des Garçons black lace dress — 2012

Designer Marc Jacobs’ daring, Comme des Garçons lace dress he wore to the 2012 Met Gala, was a fashion moment that lives in our minds rent-free. The sheer dress was avant-garde chic yet playful. Its web-like design provided a striking contrast to the crisp, white boxers Jacobs wore beneath. By boldly subverting traditional notions of menswear and embracing a look that was both feminine and futuristic, Jacobs made a powerful statement about fashion’s ability to challenge, provoke, and inspire.

10. Pharrell Williams’ Vivienne Westwood hat — 2014 

American musician Pharrell Williams’ audacious, Vivienne Westwood-designed hat, which he wore to the 2014 Grammys was a stroke of sartorial genius. The oversized, Mountie-inspired design, with its exaggerated brim and proportions, instantly polarised opinions and sparked a global conversation. By embracing the absurdity and whimsy of Westwood’s design, Williams tapped into the Grammy’s spirit of creative experimentation, transforming a mere accessory into an unforgettable fashion moment.

11. Jared Leto carrying a replica of his own head as an accessory — 2019

Jared Leto’s show-stopping, ‘head’-turning accessory at the 2019 Met Gala was a surrealist masterpiece that left onlookers agog. Designed by Alessandro Michele for Gucci, the disembodied head was a clever accessory to sport for that year’s exhibition theme “Camp: Notes on Fashion”.

12. When Pope Rihanna blessed us — 2018

Image: Courtesy of Instagram/@maisonmargiela/Maison Margiela

Barbadian musician-actor Rihanna walking the Met carpet in a Catholicism-inspired gown designed by Maison Margiela’s John Galliano is unequivocally one of the most iconic fashion moments of the 21st century. The custom-made, papal-themed ensemble, which included a mitre-style headpiece, an intricately beaded bishop’s cloak, and a pearl-encrusted corset, was a masterclass in sartorial audacity and reverence. 

RiRi not only paid homage to the theme of the evening, “Heavenly Bodies: Fashion and the Catholic Imagination,” but also cemented her status as a fashion trailblazer. The look has since been endlessly referenced, memed and revered, solidifying its place in the annals of fashion history.

13. Björk’s iconic swan dress — 2001

Bjork
Image: Courtesy Cristiano Del Riccio, CC BY-SA 2.0, via Wikimedia Commons

Icelandic singer Björk’s majestic, full-body swan costume, designed by Marjan Pejoski, was a show-stopping sensation at the 73rd Academy Awards where she was nominated in the Best Original Song category for her track “I’ve Seen It All”. This avant-garde masterpiece, featuring a full swan’s head and neck, redefined the boundaries of red-carpet fashion and solidified Björk’s status as a fearless fashion iconoclast.  

14. Priyanka Chopra’s Ralph Lauren trench coat — 2017

biggest fashion moments
Priyanka Chopra made her Met Gala debut in 2017 with Nick Jonas (Image: Courtesy of Instagram/@priyankachopra/Priyanka Chopra)

Priyanka Chopra‘s Ralph Lauren-designed trench coat gown for the 2017 Met Gala is another seminal fashion moment that continues to inspire awe. The custom-made, velvet trench coat, with its dramatic train and power collars, was a stroke of genius, reimagining the classic, utilitarian design as a show-stopping, haute couture masterpiece. The look has since established the former Miss World as a global fashion icon.

15. The ‘leg’endary Angelina Jolie thigh-slit gown — 2012

Angelina Jolie’s black Atelier Versace gown, which she wore to the 84th Academy Awards, made fashion enthusiasts worldwide sit up and take note. The custom-made, silk velvet design featured a dramatic, daring thigh-high slit that Jolie famously accentuated by posing with one leg artfully extended, giving paparazzi and tabloids fodder that was both glamorous and provocative. 

Jolie birthed a fall trend, with labels such as Balmain and Jean Paul Gaultier bringing thigh-high slits to their runways soon after and stars like Beyoncé and Nicole Scherzinger pulling off similar slit dresses.

16. When Rihanna shone ‘bright like a diamond’ in her naked dress — 2014 

Rihanna’s sheer Adam Selman gown, which she wore to accept the Council of Fashion Designers of America Awards (CFDA) Fashion Icon Award in 2014, was another of the pop star’s iconic fashion moments. The custom Swarovski-crystal-encrusted design, featuring a plunging neckline, high-cut hem, and strategically placed mesh panels, was an unapologetic celebration of the female form, as well as the “Diamonds” singer embracing her sensuality.

17. Beyoncé celebrating African American culture at Coachella — 2018 

Beyoncé’s historic 2018 Coachella performance was a masterclass in musical genius, cultural relevance, and fashion excellence. Her custom Balmain ensemble, designed by Olivier Rousteing, was a dazzling ode to Historically Black Colleges and Universities (HBCUs), with its intricate, Greek-inspired patterns and majestic, drum-major silhouette. 

As Beyoncé strode confidently across the stage, her look was a powerful celebration of African American culture, identity, and excellence. The resulting images of Queen Bey in all her glory defined Balmain finery at its best.

18. Billy Porter’s tuxedo gown — 2019

Pose star Billy Porter, known for championing gender-fluid style, shattered a sartorial barrier in this attire (Image: Courtesy of Instagram/@theebillyporter/Billy Porter)

Billy Porter’s custom Christian Siriano tuxedo gown, which he wore to the 91st Academy Awards, challenged the outdated norms of red carpet attire and celebrated the beauty of fluidity and self-expression. The velvet, silk-lined design, which featured a classic tuxedo jacket on top and a flowing, ball-gown skirt below, seamlessly merged traditional masculine and feminine silhouettes.

Porter’s bold, unapologetic choice sparked a global conversation about fashion, identity, acceptance and inclusivity. 

19. Blake Lively’s Met Gala gown inspired by the Statue of Liberty — 2022

At the 2022 Met Gala, Blake Lively dazzled in a custom Versace gown as a masterful tribute to the iconic Statue of Liberty. The intricate, hand-beaded design, which featured a flowing train that transformed from a soft, celestial blue to a vibrant, copper hue as the lights caught it, was an enamouring work of art. This innovative, colour-changing effect added an extra layer of depth and meaning to the design, evoking the statue’s iconic pedestal, which transitions from a copper-green patina to a shimmering, golden light as the sun sets. 

As Lively posed on the Met steps, her gown shimmering and shining like the statue’s iconic torch, she created an unforgettable fashion moment of the 21st century and also showcased the innovative artistry and technical prowess of Atelier Versace.

20. Bad Bunny’s backless Jacquemus suit — 2023 

biggest fashion moments
The Puerto Rican singer wore this attire as a tribute to Karl Lagerfeld and his incredible legacy (Image: Courtesy of Instagram/@jacquemus/Jacquemus)

Bad Bunny’s daring, custom Jacquemus suit, which he wore to the 2023 Met Gala, was a fashion tour-de-force that boldly redefined traditional notions of menswear. The sleek, backless design, crafted from ivory-coloured silk, was dramatically elevated by a stunning, hand-crafted floral train that emerged from the suit’s shoulders.

Well, Bad Bunny x Jacquemus, is never not iconic!

21. Zendaya’s tribute to Cher in a dazzling vintage gown — 2024

Zendaya has served more looks in the recent years than any other young celebrity. In a dazzling display of sartorial tribute, the Dune star channelled her inner Cher at the 2024 Rock & Roll Hall of Fame induction ceremony. As she took the stage to introduce the music legend, Zendaya stunned in a vintage 2001 Bob Mackie gown, its shimmering fabric and open bodice evoking the iconic style of her idol. The dress bore an uncanny resemblance to a 1972 Bob Mackie design worn by Cher, drawing parallels between these two fashion icons. 

With her dark hair styled in sleek, pin-straight locks and a middle part, Zendaya’s transformation into a Cher doppelganger was complete, paying homage to the music titan’s legacy and timeless style.

22. Cate Blanchett’s Swarovski Armani Privé gown — 2007

Cate Blanchett’s appearance at the 79th Academy Awards in a dazzling Armani Privé gown encrusted with Swarovski crystals is, without a doubt, an iconic fashion moment that has stood the test of time. The gunmetal-hued, floor-length masterpiece, valued at a staggering USD 200,000 (SGD 2,62,151 approximately) is one of the most expensive red-carpet dresses of all time, a fact that speaks for the exceptional craftsmanship and attention to detail that went into its creation. 

23. Timothée Chalamet’s bold backless red halter top — 2022 

Chalamet wore this daring outfit at the premiere of Bones and All, his second collaboration with director Luca Guadagnino (Image: Courtesy of Instagram/@tchalamet/Timothée Chalamet)

Timothée Chalamet’s style peaked here. The Call Me By Your Name (2017) actor donned a backless red halter top at the 2022 Venice Film Festival, igniting a fashion frenzy that nearly broke the internet. The bold, Ermanno Scervino-designed ensemble, featuring a sleek, sleeveless silhouette and a dramatic, exposed back, was pure perfection. Chalamet’s lean body, curly hair and effortless charm sparked a Twitter meltdown, with fans and fashion enthusiasts alike praising the star’s daring style and confidence.

24. Anne Hathaway’s stunning custom Atelier Versace gown — 2023

biggest fashion moments
Image: Courtesy of Instagram/@annehathaway/Anne Hathaway

Anne Hathaway’s custom Atelier Versace gown at the 2023 Met Gala celebrating the theme “Karl Lagerfeld: A Line of Beauty,” was a sight to behold. The hand-beaded ensemble, featuring a fitted, long-sleeved bodice and a dramatic, flowing train, brought out the timeless allure of Versace’s iconic designs, while also paying homage to Lagerfeld’s iconic legacy of elegance and precision. The pin detailing further lent an edge to the look.

25. Harry Styles’ iconic look from his “Harryween” concert at Madison Square Garden — 2021

Wrapping up our list of the biggest fashion moments of the 21st century with professional slayer Harry Styles’ Gucci-designed androgynous costume, which he wore during his “Harryween” concert at Madison Square Garden in October 2021. Dressed as Dorothy from The Wizard of Oz, Styles performed the entire show in a blue-checked dress with a bow in his hair, rouged makeup, a basket containing a stuffed Toto, and the famous sparkly red ruby shoes.

As the pop star commanded the stage with his usual confidence and charisma, his look encapsulated his fearless approach to fashion, as well as his willingness to challenge traditional notions of men’s dressing and celebrity style. 

(Hero and featured image courtesy: Instagram/@coperni/Coperni/@jacquemus/Jacquemus)

The information in this article is accurate as of the date of publication.

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