In 1999 fears were rising about the end of the world â but if civilization had actually melted down thanks to an end-of-millennium technological apocalypse, at least we would have gone out in style. (Think tiny tube tops, platform shoes and ultra-wide-legged JNCOs.)
Itâs been 25 years since the â90s closed out with an iconic year of film, television, music and fashion. Britney Spears redefined the pop star archetype, âThe Matrixâ enshrined a futuristic uniform of PVC trench coats and jet black sunglasses, and Lilâ Kim donned her infamous purple nipple pasty at the yearâs MTV Video Music Awards.
Here are 11 of the biggest style moments turning 25 this year.
American high school style dominates theaters
American teenage style has long loomed large in popular imagination, but 1999 was a canonical year for the high school genre thanks to a run of movies that included â10 Things I Hate About You,â âSheâs All That,â âDrive Me Crazyâ and âNever Been Kissedâ as well as more subversive takes including âCruel Intentionsâ and âBut Iâm a Cheerleader.â
The costuming ranged from more realistic attire (âAmerican Pieâ) to a dose of camp (âJawbreakerâ), and thereâs plenty of fashion moments to mine from each movie, from Larisa Oleynikâs two-piece red-and-pink prom look (pictured above) in â10 Thingsâ to Sarah Michelle Gellarâs rich-girl vixen getups from âCruel Intentions.â
Some of the sartorial tropes became so played out that they were spoofed just two years later in âNot Another Teen Movieâ â including, of course, the ugly duckling who removes her glasses and is suddenly a ten.
Gwyneth Paltrow wears a baby pink dress to the Oscars
Rom-com period piece âShakespeare in Loveâ beating out war drama âSaving Private Ryanâ for Best Picture at the 1999 Academy Awards served as the eveningâs major upset. But its star, Gwyneth Paltrow, also stole the show in a bubblegum pink gown by Ralph Lauren that became the most talked-about look of the night.
Paltrowâs romantic dress was read by some as a little too saccharine â it certainly looked like nothing else on the red carpet â but it has endured over the years as one of the most memorable Oscars looks. Paltrow, who is known to hold onto her red-carpet dresses (and pass them down to her daughter, Apple), revived it recently in a campaign for her lifestyle brand, Goop, recreated faithfully down to the slicked-back, side-parted bun.
Britney Spears poses in scandalous bedroom shoot for Rolling Stone
Itâs been 25 years since Britney Spears was pronounced âTeen Queenâ by Rolling Stone, with an explosive magazine cover featuring the newly-debuted pop sensation in her underwear in bed, cradling a purple Teletubby on top of pink satin sheets.
The provocative photograph, lensed by David LaChapelle, was released in the months after Spearsâ debut music video, single and album ââŚBaby One More Timeâ launched her to superstardom. Though Spears was 18 at the time of the shoot, the image drew criticism for sexualizing a teen girl in what was made to look like her childhood bedroom â but it has since become one of the most famous magazine covers of all time.
The Matrixâ creates a dress code for the dystopian cyberfuture
Leather, long overcoats and ink-black shades may have already been familiar style notes in sci-fi flicks, but âThe Matrixâ (courtesy of costume designer Kym Barrett) created an instantly recognizable sartorial style that mixed cybergoth aesthetics, the work of subversive runway designers like Helmut Lang, and dystopian anime influences including âGhost in the Shell.â
The blockbuster wasnât the only big moment for leather pants that year, largely thanks to Ricky Martin (What is âThe Matrixâ if not an example of âLivinâ la Vida Loca,â after all?) but the film franchise had an enduring impact on fashion. It has become the touchstone for dark, dystopian fashion, and its DNA can be seen anywhere thereâs a statement black trench and slick leather tailoring. Just after the release of the first film, John Gallianoâs dramatic fall couture collection for Dior reportedly took notes from its costuming, while Balenciaga paid tribute in a 2019 campaign film, as well as in many subsequent runway shows.
Alexander McQueen provokes in New York with controversial, Islam-inspired collection
Just one year after Alexander McQueen made fashion history with paint-spraying robots who completed ballet dancer Shalom Harlowâs dress on the runway, the lauded British designer put on a spectacle for his highly anticipated US debut in New York â to very mixed reviews. âEye,â inspired by Islamic dress, mixed sports- and fetishwear with traditional garments such as the niqÄb and burqa, with models (including Gisele Bündchen) in dark, heavy eyeshadow. Known for his theatrical flair, McQueen upped the ante with staging that included a flooded runway that turned into a bed of nails, with models suspended overhead.
âThe Virgin Suicidesâ romanticizes the humble nightgown
When the airy white, lightly frilled ânap dressâ by Hill House went viral during the first year of the Covid-19 pandemic, it offered feminine, daydreamy alternative to pyjamas and athleisure that could inject some romance into listless days of housebound monotony. But, 25 years ago, Sofia Coppolaâs âThe Virgin Suicidesâ had perfected that aesthetic, capturing the complex psyches of teenage girls in diaphanous white gowns. The film follows the Lisbon sisters, who are kept isolated at home by their overprotective parents following one of the girlsâ suicide attempts, and the boys who become enamoured by them.
Though the directorâs debut fell short at the box office, it has blossomed over time, and Coppolaâs deceptively halcyon vision of suburbia had a slow-burn impact on visual culture.
Lilâ Kim enters a single purple pasty into the annals of fashion
Bare breasts had a big year on runways and red carpets this past year, but none of them could quite match Lilâ Kimâs iconic, peekaboo purple jumpsuit, which would have left her left breast entirely exposed if not for a single artfully placed clamshell pasty.
The rapperâs glittering, showstopping look was the talk of the 1999 MTV Video Music Awards, especially as she took the stage with Mary J. Blige and Diana Ross, the latter of whom cupped her breast in an unscripted moment. Rossâs uninvited touch would likely be more criticized today, but Kim told XXL magazine last year that it was âone of (the) highlightsâ of her career.
âThe Sopranosâ debuts, with underrated fashion chops
âThe Sopranosâ wasnât lauded for its fashion credentials when it first debuted in 1999 â or, really, at any point during its supremely successful eight-year-run â but the New Jersey-based mob family have, over time, become unexpected style icons. (This writerâs Italian American father, who began wearing a pinky ring at the poker table thanks to the show, can attest to this). Rewatches and anniversaries of the HBO drama (CNN is owned by HBOâs parent company, Warner Bros. Discovery) have spawned many new headlines with fresh sartorial analysis, from Tony Sopranoâs short-sleeve button-downs, with a touch of bada bing, to his wife Carmelaâs quintessential Jersey mom wardrobe.
The castâs layered gold jewelry, tracksuits, golf shirts and animal prints arenât exactly understated, but they never looked out of place in the stateâs suburbs. Perhaps they were pioneers of stealth wealth â well, Jerseyâs version of stealth wealth.
TLC defines futuristic fashion with âNo Scrubsâ
TLCâs music video for âNo Scrubsâ perfectly encapsulated â90s futurism â a silvery space station setting with a heavy dose of fetishwear. Over the â90s, the trio evolved their coordinated style from playful, oversized streetwear (including safety-pinned condom accessories) to include BDSM, raver and space-inspired influences. Out of all the matchy-matchy group looks that dominated music videos and red carpets in the â90s and â00s, T-Boz, Left Eye and Chilli took the most risks.
In the âNo Scrubsâ 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 may have landed on worst-dressed lists when she stepped onto the 1999 Oscars red carpet in a backward John Galliano tuxedo, but she was sure that it would stand the test of time as a fashion-forward choice. The superstar told People in 2017 that the world just wasnât ready for her experimental all-white ensemble, which she topped off with a large asymmetrical white hat and shades.
âWhen I wore that look⌠everyone was wearing dresses, not pants,â she said. âIf I would do this today it would work. It was avant-garde at the time. And it doesnât matter, you just have to assume what you wear, you wear, and I did.â
Dion carried the look with confidence, and she has eventually been proven right â backwards tailoring hit the runway in 2023, from Burberry to Maison Margiela.
Pamela Anderson wears a big pink hat
Pamela Andersonâs skin-baring, maximalist looks often turned heads in the 1990s, but perhaps none more so than one infamous fluffy pink hat. The actor and modelâs oversized bubblegum-hued bucket hat made its debut at the 1999 MTV Video Music Awards, paired with an ultra-cinched white corset and bedazzled pants. Designed by Ivy Supersonic, a friend of Andersonâs ex-husband Tommy Lee, the hat was a contrast to Leeâs simple brown trench coat, which he wore without anything underneath.
Kim Kardashian, Kelly Ripa and Megan Fox have all paid homage to Andersonâs look, as has the âBaywatchâ star herself. In 2022, she arrived at the Jacquemus spring-summer 2023 runway show in a dramatic feathered white hat with a familiar oversized silhouette.