In the 1990s and early 2000s, the Academy Awards red carpet underwent a sea change. During the nascent era of the celebrity stylist, fearless stars not only began donning high-end designer labels (like awards show pioneer Armani) but also flouted traditional Oscar dress-code decorum in new ways, sometimes inviting the wrath of prevailing critics.

Among the looks that shook things up — and made an indelible impression on fashion and pop culture — were Sharon Stone’s proto-high-low dressing, Jada Pinkett Smith’s sensational two-piece set, actresses in one-of-a-kind vintage looks and a still controversial aughties affectation (the whale tail).

Nearly three decades later, the influence of the era’s Oscar red carpet can be seen all over the TikTok generation, Fall 2023 runways and, yes, once again on recent awards-season red carpets.

Sartorial Protest

In 1995, Lizzy Gardiner accepted her Oscar in a gown she created out of 254 American Express gold cards. The Adventures of Priscilla, Queen of the Desert costume designer made worst-dressed lists — and an audacious statement on a still pressing issue: socioeconomic disparity. “[The cards] said something about someone’s wealth and standing,” says Gardiner. Adds stylist Zadrian Smith, of duo Zadrian +

Sarah, “It [was] a statement on class, commerce and social capital.” Gardiner’s look was a harbinger of a wave of recent red carpet looks that weave in messaging, from colleague Jenny Beavan’s tuxedo hand-painted to protest pay inequity last year to Natalie Portman’s 2020 Dior cape embroidered with the names of snubbed female directors.

Grunge-Glam Slip Dresses

“If you remember, there was a little fashion moment with slip dresses, flip-flops and tousled hair,” says stylist Phillip Bloch of the 1990s grunge trend, which was elevated at the Oscars by such stars as Gwyneth Paltrow (in beaded yet minimalist Calvin Klein); slip-dress queen Courtney Love (in bias-cut Versace); and Salma Hayek (in an Armani tank-style dress, with an Audrey Hepburn-referential tiara). “A slip dress can convey so many different points of view,” says Alexis Novak, owner of Hollywood-loved company Tab Vintage, of the versatility of the revived trend, seen recently on Olivia Rodrigo (in a Miu Miu sheath at the Grammys) and Kendall Jenner (in Khaite Carina at the CFDA Awards).

High-Low Individualism

In 1996, a last-minute Oscars wardrobe crisis forced Sharon Stone to pull together a self-expressive and tradition-defying mix of her own wardrobe essentials: a black Gap turtleneck, a Valentino maxi skirt and a velvet Armani tuxedo dress. Two years later, she repeated the successful formula, pairing her then-husband’s white Gap button-down with a lilac Vera Wang skirt. “High-low, high-low,” intones Smith of Stone’s dressing foresight — long before the term became popularized in everyday fashion lexicon. At the last Oscars, Law Roach dressed Zendaya in a Stone-referential Valentino Couture ensemble, while at this year’s Critics Choice Awards, Cate Blanchett’s taupe shirt-and-skirt set by Max Mara also evoked Stone’s insouciant approach.

Belly-Baring Sets

For the 1997 Oscars, Jada Pinkett Smith wanted to look “modern, hip and cool,” says Bloch, then her stylist. So he asked Gianni Versace to slash a shimmery green halter gown into a crop top and low-slung skirt. “She was the inspiration — 100 percent — Jada was Jada,” recalls Bloch about Pinkett Smith’s prescient vision. Fast-forward to 2023, and sets that bare midriffs are “so Gen Z,” says Novak. Matching sets abound on Euphoria, while Taylor Swift stunned in a midriff-revealing Roberto Cavalli two-piece look at the Grammys. Among her clients, Novak notes a high demand for “1990s Jada Pinkett Smith” looks across the board: “Chain-mail anything, slinky anything. Lots and lots of skin.”

N’aughties Opulence

Like it or not, the aughts-era “whale tail” — i.e., an irreverently exposed G-string — returned with a vengeance around 2019, highlighted by Hailey Bieber wearing a pink trompe l’oeil interpretation at the Met Gala. But back in 2000, Blanchett sanctioned the cheeky flourish — commonplace at the MTV VMAs — for the esteemed Academy Awards. The low-plunge back on her Jean Paul Gaultier gown framed antique Indian jewels formed into a thong- referential shape by jeweler Cynthia Bach and stylist Jessica Paster. “It’s classic business in the front and ‘I do my own thing’ from the back,” says stylist Sarah Edmiston, of Zadrian + Sarah, noting that the look bespeaks “the contradictions of the woman in the contradictions of the dress.”

Vintage, Meet Sustainability

In 2001, Renée Zellweger generated headlines in a breathtaking 1950s lemon-yellow Jean Dessès gown from Lily et Cie. “Originals make history,” says Rita Watnick, owner of Lily et Cie, one of Hollywood’s vintage meccas. That same year, Julia Roberts accepted her Oscar in an archival 1992 Valentino Couture gown. At the time, “exclusivity” was one of the allures of one-of-a-kind vintage, recalls Watnick (who was also the source for Jennifer Lopez’s dreamily draped Jean Dessès dress for the 2006 Oscars). Now, with the world in the throes of climate disaster, a slew of stars — from Cannes to major awards shows — are falling for vintage. For many, it’s because reuse sends a new message. “[They] are leading the charge of sustainable fashion,” says Novak, “and showing it is cool to wear something again.”

Sheer Winning Style

To recall Halle Berry making history as the first — and still only — Black woman to win the best actress Oscar, in 2002 for Monster’s Ball, is to remember her moving tears and her trophy triumphantly raised in the air. She did it wearing an Elie Saab Couture gown with intricate floral embroidery on the sheer bodice. “We re-beaded it for the waist up because that’s the shot,” recalls Bloch. “Her dress was just so exquisite.” Strategically placed adornments on illusion bodices — or entire dresses — made a return in the Fall 2023 collections, seen at runway presentations by Christian Siriano, Sandy Liang, Carolina Herrera, Naeem Khan and LaQuan Smith.

Marigold Standard

“It was considered an unflattering color and a weird color for a red carpet gown, but it felt young and cool to us,” says stylist Kate Young, looking back at the way Michelle Williams took a risk at the 2006 Oscars in a fluttery saffron Vera Wang dress. Well, the stunning shade of yellow is back and stronger than ever. As part of its Fall 2023 report, color authority Pantone just christened the hue “High Visibility.” Marigold also brightened up Fall-Winter 2023 collections by Proenza Schouler, Burberry and Tanya Taylor. “It’s still so fresh,” says Novak. Yellow was a big trend at the 2023 SAG Awards as well, as seen on Viola Davis, Angela Bassett and Niecy Nash.

This story first appeared in the March 8 issue of The Hollywood Reporter magazine. Click here to subscribe.