The most iconic 1999 style moments turning 25 this year

Larisa Oleynik's two-piece prom dress in "10 Things I Hate About You" was one of many outfits that defined American teen movies in 1999.

Larisa Oleynik’s two-piece prom dress in “10 Things I Hate About You” was one of many outfits that defined American teen movies in 1999.Archive Photos/Moviepix/Getty ImagesCNN — 

In 1999 fears were rising about the end of the world — 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.)

It’s been 25 years since the ’90s closed out with an iconic year of film, television, music and fashion. Britney Spears redefined the pop star archetype, “The Matrix” enshrined a futuristic uniform of PVC trench coats and jet black sunglasses, and Lil’ Kim donned her infamous purple nipple pasty at the year’s 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 “10 Things I Hate About You,” “She’s All That,” “Drive Me Crazy” and “Never Been Kissed” as well as more subversive takes including “Cruel Intentions” and “But I’m a Cheerleader.”

The costuming ranged from more realistic attire (“American Pie”) to a dose of camp (“Jawbreaker”), and there’s plenty of fashion moments to mine from each movie, from Larisa Oleynik’s two-piece red-and-pink prom look (pictured above) in “10 Things” to Sarah Michelle Gellar’s rich-girl vixen getups from “Cruel Intentions.”

Some of the sartorial tropes became so played out that they were spoofed just two years later in “Not Another Teen Movie” — 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

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

Gwyneth Paltrow in Ralph Lauren. Paltrow took home Best Actress for “Shakespeare in Love.”Kevin Mazur/WireImage/Getty Images

Rom-com period piece “Shakespeare in Love” beating out war drama “Saving Private Ryan” for Best Picture at the 1999 Academy Awards served as the evening’s 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.

Paltrow’s romantic dress was read by some as a little too saccharine — it certainly looked like nothing else on the red carpet — 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

Britney Spears and Tinky Winky's iconic cover shoot.

Britney Spears and Tinky Winky’s iconic cover shoot.From Rolling Stone

It’s been 25 years since Britney Spears was pronounced “Teen Queen” 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 Spears’ debut music video, single and album “…Baby One More Time” 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 — but it has since become one of the most famous magazine covers of all time.

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

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

Carrie-Ann Moss and Keanu Reeves’s styling in “The Matrix” has been endlessly replicated.Maximum Film/Alamy Stock Photo

Leather, long overcoats and ink-black shades may have already been familiar style notes in sci-fi flicks, but “The Matrix” (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 “Ghost in the Shell.”

The blockbuster wasn’t the only big moment for leather pants that year, largely thanks to Ricky Martin (What is “The Matrix” if not an example of “Livin’ la Vida Loca,” 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 there’s a statement black trench and slick leather tailoring. Just after the release of the first film, John Galliano’s 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

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

McQueen presented “Eye” as Hurricane Floyd threatened New York with intense rainfall.Patrick McMullan/Getty Images

Just one year after Alexander McQueen made fashion history with paint-spraying robots who completed ballet dancer Shalom Harlow’s dress on the runway, the lauded British designer put on a spectacle for his highly anticipated US debut in New York — to very mixed reviews. “Eye,” inspired by Islamic dress, mixed sports- and fetishwear with traditional garments such as the niqāb 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.

“The Virgin Suicides” romanticizes the humble nightgown

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

Kirsten Dunst starred in “The Virgin Suicides” as rebellious Lisbon sister Lux.Paramount Classics/Everett Collection

When the airy white, lightly frilled “nap dress” by Hill House went viral during the first year of the Covid-19 pandemic, it offered feminine, daydreamy alternative to pajamas and athleisure that could inject some romance into listless days of housebound monotony. But, 25 years ago, Sofia Coppola’s “The Virgin Suicides” 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 girls’ suicide attempts, and the boys who become enamored by them.

Though the director’s debut fell short at the box office, it has blossomed over time, and Coppola’s deceptively halcyon vision of suburbia had a slow-burn 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.

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 had a big year on runways and red carpets this past year, but none of them could quite match Lil’ Kim’s iconic, peekaboo purple jumpsuit, which would have left her left breast entirely exposed if not for a single artfully placed clamshell pasty.

The rapper’s 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. Ross’s uninvited touch would likely be more criticized today, but Kim told XXL magazine last year 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.

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

“The Sopranos” wasn’t lauded for its fashion credentials when it first debuted in 1999 — or, really, at any point during its supremely successful eight-year-run — but the New Jersey-based mob family have, over time, become unexpected style icons. (This writer’s 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 HBO’s parent company, Warner Bros. Discovery) have spawned many new headlines with fresh sartorial analysis, from Tony Soprano’s short-sleeve button-downs, with a touch of bada bing, to his wife Carmela’s quintessential Jersey mom wardrobe.

The cast’s layered gold jewelry, tracksuits, golf shirts and animal prints aren’t exactly understated, but they never looked out of place in the state’s suburbs. Perhaps they were pioneers of stealth wealth — well, Jersey’s version of stealth wealth.

TLC defines futuristic fashion with “No Scrubs”

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

“No Scrubs” sent TLC’s third album “FanMail” into the stratosphere.From TLC/LaFace Arista Records

TLC’s music video for “No Scrubs” perfectly encapsulated ’90s futurism — a silvery space station setting with a heavy dose of fetishwear. Over the ’90s, 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 ’90s and ’00s, T-Boz, Left Eye and Chilli took the most risks.

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.

Celine Dion’s John Galliano suit was a true 360-degree look.Kevin Mazur/WireImage/Getty Images

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 wasn’t ready for her experimental all-white ensemble, which she topped off with a large asymmetrical white hat and shades.

“When I wore that look… everyone was wearing dresses, not pants,” she said. “If I would do 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 right — backwards 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.

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 skin-baring, maximalist looks often turned heads in the 1990s, but perhaps none more so than one infamous fluffy pink hat. The actor and model’s 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 Anderson’s ex-husband Tommy Lee, the hat was a contrast to Lee’s simple brown trench coat, which he wore without anything underneath.

Kim Kardashian, Kelly Ripa and Megan Fox have all paid homage to Anderson’s look, as has the “Baywatch” 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.

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