25 Iconic Style Moments from 1999: Celebrating their 25th Anniversary

Fears of the end of the world were on the rise in 1999, but if civilization had actually collapsed due to a technological apocalypse at the end of the millennium, at least we would have gone out in style. (Think tiny tube tops, platform shoes, and ultra-wide-legged JNCOs.)

It has been 25 years since the 90s came to a close with an iconic year of film, television, music, and fashion. Britney Spears redefined the pop star archetype, "The Matrix" popularized a futuristic uniform of PVC trench coats and jet black sunglasses, and Lil Kim made headlines with her infamous purple nipple pasty at the MTV Video Music Awards.

Here are 11 of the biggest style moments turning 25 this year.

American high school style dominates theaters

American teenage fashion in 1999 made a lasting impact on popular culture, especially in high school movies like "10 Things I Hate About You," "She's All That," "Drive Me Crazy," and "Never Been Kissed," as well as the more subversive "Cruel Intentions" and "But I'm a Cheerleader." The movies featured a range of realistic and campy costumes, including standout fashion moments like Larisa Oleynik's red-and-pink prom look in "10 Things" and Sarah Michelle Gellar's rich-girl vixen outfits in "Cruel Intentions."

Gwyneth Paltrow wears a baby pink dress to the Oscars

Some of the fashion trends became so overdone that they were parodied just two years later in "Not Another Teen Movie," including the classic 'ugly duckling' transformation where the character removes her glasses and becomes instantly more attractive.

Gwyneth Paltrow in Ralph Lauren. Paltrow took home Best Actress for "Shakespeare in Love."

Gwyneth Paltrow's bubblegum pink gown by Ralph Lauren became the most talked-about look of the 1999 Academy Awards, overshadowing the surprise win of "Shakespeare in Love" for Best Picture over "Saving Private Ryan." The rom-com period piece caused a major upset at the event.

Britney Spears poses in scandalous bedroom shoot for Rolling Stone

Paltrow's enchanting gown may have been seen as overly sweet by some—it certainly stood out on the red carpet—but it has stood the test of time as one of the most unforgettable Oscars outfits. Paltrow, who is known for keeping her red-carpet gowns (and passing them down to her daughter, Apple), recently brought it back in a campaign for her lifestyle brand, Goop, recreated with precision down to the sleek, side-parted bun.

Britney Spears and Tinky Winky's iconic cover shoot.

Britney Spears was crowned the "Teen Queen" by Rolling Stone 25 years ago. She adorned the magazine cover as a newly-emerged pop sensation, posing in her underwear in bed, cuddling a purple Teletubby on brightly colored satin sheets.

“The Matrix” creates a dress code for the dystopian cyberfuture

The controversial photo, captured by David LaChapelle, emerged in the aftermath of the release of Spears' debut music video, single, and album "…Baby One More Time" which catapulted her to stardom. Despite being 18 at the time of the photo shoot, the image faced backlash for sexualizing a teenage girl in what appeared to be her childhood bedroom. Nevertheless, it has gone on to become one of the most iconic covers in magazine history.

Carrie-Ann Moss and Keanu Reeves's styling in "The Matrix" has been endlessly replicated.

The Matrix, styled by costume designer Kym Barrett, introduced a distinctive sartorial look that combined cybergoth influences, the designs of subversive runway creators like Helmut Lang, and dystopian anime elements from "Ghost in the Shell." Leather, long overcoats, and ink-black shades, already familiar in sci-fi films, were elevated to create a unique and iconic style.

The leather pants trend was not only popularized by the blockbuster that year, thanks in large part to Ricky Martin (What is "The Matrix" if not an example of "Livin la Vida Loca," after all?) but the film franchise had a lasting impact on fashion. It has become the reference point for dark, dystopian fashion, and its influence can be seen wherever there's a striking black trench and sleek leather tailoring. Just after the release of the first film, John Galliano's dramatic fall couture collection for Dior reportedly drew inspiration from its costumes, while Balenciaga paid homage in a 2019 campaign film, as well as in many subsequent runway shows.

Alexander McQueen provokes in New York with controversial, Islam-inspired collection

McQueen presented "Eye" as Hurricane Floyd threatened New York with intense rainfall.

Patrick McMullan/Getty Images

Just one year after Alexander McQueen made waves in the fashion world with paint-spraying robots finishing ballet dancer Shalom Harlow's dress on the runway, the celebrated British designer made his highly anticipated US debut in New York to mixed reviews. Dubbed "Eye," the collection drew inspiration from Islamic dress, blending sports and fetishwear with traditional garments like the niqāb and burqa. Models, including Gisele Bündchen, sported dark, heavy eyeshadow. McQueen, known for his dramatic flair, elevated the show with a flooded runway that transformed into a bed of nails, with models suspended overhead.

“The Virgin Suicides” romanticizes the humble nightgown

Kirsten Dunst starred in "The Virgin Suicides" as rebellious Lisbon sister Lux.

Paramount Classics/Everett Collection

Hill House's viral "nap dress" provided a feminine alternative to pajamas and athleisure during the Covid-19 pandemic's early days, injecting romance into mundane, housebound life. Years before, Sofia Coppola's "The Virgin Suicides" captured the same ethereal aesthetic, delving into the complex world of teenage girls in diaphanous white gowns. The film tells the story of the Lisbon sisters, isolated at home by their overprotective parents after one of the girls attempts suicide, and the boys who become infatuated with them.

While the film initially struggled at the box office, it has gained recognition over time, and Coppola's serene portrayal of suburbia has had a lasting impact on visual culture.

Lil Kim enters a single purple pasty into the annals of fashion

Lil' Kim's purple jumpsuit was made of embellished Indian bridal fabric, designed by her stylist Misa Hylton.

Mitchell Gerber/Corbis/Getty Images

Bare breasts made a big impact on runways and red carpets last year, but none could compare to Lil Kim's iconic purple jumpsuit, revealing her left breast saved only by a single artfully placed pasty. Her showstopping look at the 1999 MTV Video Music Awards, where she took the stage with Mary J. Blige and Diana Ross, caused quite a stir, especially when Ross unexpectedly touched her breast. While this would likely be criticized today, Kim revealed in an interview that it was one of the highlights of her career.

“The Sopranos” debuts, with underrated fashion chops

James Gandolfini and Edie Falco as Tony and Carmela Soprano fit the bill for quiet mob luxury.

HBO/Everett Collection

"The Sopranos" did not receive praise for its fashion when it first aired in 1999, or at any point during its highly successful eight-year run. However, the New Jersey-based mob family has unexpectedly become style icons over time. Rewatches and anniversaries of the HBO drama have led to fresh sartorial analysis, with headlines focusing on the casts' fashion choices, such as Tony Soprano's short-sleeve button-downs and his wife Carmela's quintessential Jersey mom wardrobe. The show's cast often sported layered gold jewelry, tracksuits, golf shirts, and animal prints that may not have been understated, but they suited the suburban setting. Perhaps they were pioneers of "stealth wealth," at least in New Jersey.

TLC defines futuristic fashion with “No Scrubs”

"No Scrubs" sent TLC's third album "FanMail" into the stratosphere.

From TLC/LaFace Arista Records

TLC's music video for "No Scrubs" perfectly captured 90s futurism, featuring a silvery space station setting and a heavy dose of fetishwear. Over the 90s, the trio evolved their coordinated style from playful, oversized streetwear, including safety-pinned condom accessories, to incorporate BDSM, raver, and space-inspired influences. T-Boz, Left Eye, and Chilli took the most risks out of all the matchy-matchy group looks that dominated music videos and red carpets in the 90s and 00s.

In the "No Scrubs" video, they had several outfit changes, but the most memorable were their black midriff-baring PVC takes on space suits, complete with harnesses. After the anthem dominated the airwaves throughout the year, they turned heads at the MTV Video Music Awards, performing the single in hot red versions of the suits.

Celine Dion dons that divisive backwards tuxedo

Celine Dion's John Galliano suit was a true 360-degree look.

Kevin Mazur/WireImage/Getty Images

Celine Dion may have made worst-dressed lists when she arrived at the 1999 Oscars in a backward John Galliano tuxedo, but she was confident that her fashion choice would stand the test of time. The superstar explained to People in 2017 that her experimental all-white outfit, complete with a large asymmetrical white hat and sunglasses, was ahead of its time. She noted, "When I wore that look, everyone was wearing dresses, not pants. If I did this today, it would work. It was avant-garde at the time. And it doesn't matter, you just have to assume what you wear, you wear, and I did."

Dion carried the look with confidence, and she has eventually been proven rightbackwards tailoring hit the runway in 2023, from Burberry to Maison Margiela.

Pamela Anderson wears a big pink hat

Pam Anderson's feathered pink hat stood out during a night of many looks at the 1999 MTV VMAs.

Evan Agostini/Hulton Archive/Getty Images

Pamela Anderson's attention-grabbing, extravagant outfits were a staple of the 1990s, but none caused as much of a sensation as her infamous fluffy pink hat. The actress and model donned an oversized bubblegum-colored bucket hat at the 1999 MTV Video Music Awards, paired with a tightly cinched white corset and bedazzled pants. Created by Ivy Supersonic, a friend of Anderson's ex-husband Tommy Lee, the hat provided a stark contrast to Lee's simple brown trench coat, which he wore without anything underneath.

Kim Kardashian, Kelly Ripa, and Megan Fox have all emulated Anderson's style, as has the "Baywatch" star herself. Anderson made a dramatic entrance at the 2022 Jacquemus spring-summer 2023 runway show, sporting a feathered white hat with a distinct oversized silhouette.