MINIMALISM

Sometimes the biggest statement can be an understatement. At the 44th Oscars in 1972, Jane Fonda (right) chose an off-the-rack Yves Saint Laurent suit with a Mao collar as an anti-Vietnam war protest. Fonda won the Best Actress Oscar that night for her role in Klute, which also starred Donald Sutherland (left) and her shag haircut. |  Frank Edwards/Fotos International/Getty Images
Sharon Stone (left) followed up on her less-is-more ethos established two years prior at the 1996 Oscars with her subversive Gap black turtleneck – making high-low a thing. At the 1998 Awards, she casually tucked a provocative unbuttoned-to-the-navel white shirt from Gap into a satin Vera Wang skirt, and collars have been popped and sleeves rolled ever since. OG nepo-baby Anjelica Huston (far right) managed to outshine Hollywood’s hottest star, her beau Jack Nicholson (second from right), at the 1975 Oscars in a simple scoop-necked silhouette, letting the iridescent texture do the talking. | Mychal Watts/WireImage; Michael Ochs Archives/Getty Images

 

THE NATURAL 

 

California-girl beauty is most fitting for Hollywood’s screen queen. For her first Oscar in 1980 (she has won three and has a record-breaking 21 nominations) for Kramer vs. Kramer, Meryl Streep’s spirited blowout was an easy-breezy contrast to her structured blazer.  |  Bettmann/Getty Images
In a sea of old Hollywood glamour gowns, Cameron Diaz (left), rebel that she is, created a then-controversial boho moment at the 2002 Oscars with her loose waves, glowy makeup and Emanuel Ungaro wrap dress – she put together the look with her friend and makeup artist Gucci Westman. Since then, Westman went on to create Westman Atelier, a cult makeup treatment line. Lauren Hutton (centre), the prototype for the model-turned-pop-culture-influencer, the epitome of effortless glamour, perhaps because she styled herself for the 1975 Academy Awards in a Halston chiffon dress with a glowy bronzed face and body. No jewellery required. In 2002, Halle Berry (right) made history as the first Black woman to win an Oscar for Monster’s Ball and her look lived up to the milestone moment. Her Elie Saab gown – with an articulated draped skirt and train, illusion netting and strategically placed embroidery – remains one of the greatest Oscar looks of all time. However, the dress didn’t overshadow her because she kept it fresh with a tousled pixie cut and understated makeup that withstood the deluge of tears that erupted during her heartfelt speech. | Frank Micelotta/Getty Images; Ron Galella/Ron Galella Collection via Getty Images; Frank Micelotta/ImageDirect

 

TRUE ROMANCE 

 

Two actresses waiting in the wings to walk into history — it’s no wonder one inspired the Kelly bag and one made the Little Black Dress a key feature of modern fashion. 1956 marked the last Oscar appearance for Grace Kelly (right) before marrying Rainier III, Prince of Monaco. She wore a Helen Rose designed chiffon gown with a delicate floral print — Rose also designed Kelly’s elegant and intricate wedding dress that was so anticipated it was kept secret until two days before the wedding. Audrey Hepburn (left) was in a simple, striking white gown designed by her friend and fashion collaborator Hubert de Givenchy. Their Oscar style still reverberates today.  |  Allan Grant/The LIFE Picture Collection/Shutterstock
The first true luxury-fashion-meets-red-carpet moment was the Prada label’s lavender dress for Uma Thurman (left) at the 67th Academy Awards in 1995 – read the back story and the history of Oscar fashion in Made for Each Other: Fashion and the Academy Awards by Canadian journalist and film producer Bronwyn Cosgrave. Prada created another sleight-of-imaging for Lupita Nyong’o (centre) with what the actor described as “a blue that reminds me of Nairobi” at the 2014 Academy Awards, where she won an Oscar for Best Supporting Actress in 12 Years A Slave. Her gold and diamond headband by Fred Leighton added interest and highlights that you don’t have to be a princess to wear a tiara. Speaking of princess-ish cool girl, Gwyneth Paltrow (right) was not enamoured of the pink taffeta Ralph Lauren dress that she wore for the 1999 Oscars. The polarizing look (the House of Lauren, inspired by real-life princess Grace Kelly, was upset Paltrow removed the inner-corset on game day) became a cultural phenomenon and the dress even has its own Wikipedia page. |  Frank Trapper/Corbis via Getty Images; Axelle/Bauer-Griffin/FilmMagic; Ke.Mazur/WireImage

 

WELL SUITED

 

In the last couple of years, Celine Dion has broken the internet time and time again when styled by Law Roach in fashion curiosities like the Vêtements Titanic sweatshirt. But Dion has been playing against type since 1999, when she, with her Montreal stylist Annie Horth, shut down the red carpet in a louche fashion-forward John Galliano for Dior Haute Couture suit. Saved from looking camp by impeccable draping and tailoring, the much derided (at the time) look has made every unforgettable fashion list since. |  Jeffrey Mayer/WireImage
Dion became aware of Roach’s work after the singer’s son René-Charles Angélil told her she should dress more like Zendaya (left) – Roach has been the up-and-coming icon’s fashion godfather since the beginning of  her career on the Disney Channel. Now a bona fide fashion star – Zendaya’s looks on press tours make headlines – she shone at the 2022 Vanity Fair Oscar party in a structured Sportsmax suit with an exaggerated smoky cat-eye and slicked-down hair for an androgynous sizzle. Triple-threat template for the ages, Diana Ross (centre) attended the Oscars in 1973 for her Best Actress nomination as Billie Holiday in Lady Sings the Blues. After playing Holiday with her gowns and gardenias, and living her prior life as a sequinned Supreme, it’s no wonder Ross wanted to play against type in a disco dance-floor-ready three-piece satin Bob Mackie suit. However, Barbra Streisand (right) did want to be a funny girl; dressed by Montreal-born New York designer Arnold Scaasi in a see-through quasi sailor suit whose shimmer matched her star power. She won the Oscar for playing the legendary Broadway star Fanny Brice in, yes, Funny Girl in 1969. The outfit caused a furore, not only for its transparency but because Streisand was the first woman to wear pants to the Awards. | Doug Peters/PA Images via Getty Images; Fairchild Archive/Penske Media via Getty Images; Silver Screen Collection/Getty Images

 

HIGH-IMPACT HAUTE

 

Beyond the Oscar night tropes of mermaid dresses and old-school Hollywood glamour, Emma Stone’s decade-long creative collaboration with Louis Vuitton’s Nicholas Ghesquière has led to some of the most fashion-forward looks on the red carpet. This peplum double-tulip-shaped ensemble, in an unusual aquamarine colour, shone when she won the Oscar for Best Actress for Poor Things in 2024, despite the zipper-gate that was seen around the world.  |  Mike Coppola/Getty Images
Unusual colour cuts through the red carpet’s style clutter as a way to stand out. Exhibit A: (left) Nicole Kidman’s 1997 couture Dior dress by John Galliano – the cut, the embroidery and her understated arm candy were spectacular – but it was the unexpected chartreuse colour that pushed it into legendary territory. Ditto for Michelle Williams (far right) who attended the 78th Annual Academy Awards in 2006 with the late Heath Ledger (second from left) – both were nominated for Brokeback Mountain. Her stylist, Kate Young, commissioned a ’40s-style Vera Wang dress in an egg-yolk yellow, which Young described as unexpected but fresh and cool. Young also insisted on a red lip for the chef’s kiss. |  Jim Smeal/Ron Galella Collection via Getty Images; Frazer Harrison/Getty Images

 

CLASSIC METALLIC

 

If Oscar night is a hunt for little gold men, those who seek but do not find can lift their spirits with all that glitters on the fashion front. At this point in 1980, Lauren Hutton had entered her American Gigolo era, and while her co-star Richard Gere played it cool in Armani, she pumped up her star power in gold lamé. But, in the hands of American fashion designer Zoran, it remained chic due to its sportswear aesthetic and her mid-heeled pump. This look also makes a great case for the return of pantyhose. |  Ron Galella/Ron Galella Collection via Getty Images
When old Hollywood glamour works it does so brilliantly. Charlize Theron (left) was a past master of the mode at the 76th Annual Academy Awards in 2004, while her hair and makeup channelled the silver screen’s golden age, her Gucci dress showed designer Tom Ford’s minimalist discipline and moved the look into modernity. Despite being upset for the Oscar by ingénue Mikey Madison, Demi Moore (centre), who was nominated for The Substance in 2025, looked like the winner in an outstanding feat of design Giorgio Armani Privé. Armani’s atelier brought all of their couture techniques to the structure, draping and cut of this spectacular gown. Returning to the Oscars in 2024, the year after she became the first Asian woman to win Best Actress for Everything Everywhere All at Once, Michelle Yeoh (right) sparkled and shone in an edgy gothic-coded dress – in other words, very Balenciaga. | Ian West – PA Images/PA Images via Getty Images; Gilbert Flores/Penske Media via Getty Images; Aliah Anderson/Getty Images

 

HIGH CONTRAST

 

A fashion plate until the very end (see her Zoomer cover shoot in 2021), Cicely Tyson did not disappoint when presenting at the 1977 Oscars. Her cascading lace capelet and dramatic throws into sharp relief her bold makeup, and the power of highlighting and gloss.  |  Michael Ochs Archives/Getty Images
Daring cutouts in subversive black (well, for the Oscar’s anyway) prove that skin was in at the 2000 Academy Awards. Cate Blanchett (left) partied in the back in a liquid Jean Paul Gaultier dress adorned with gold-chain details, while at the Vanity Fair party, Jennifer Aniston (far right), whose plunging neckline of her Lawrence Steele dress, managed to upstage even her then-husband, Brad Pitt (second from left). Pitt would go on, among other things, to star with Leonardo DiCaprio (below) in Once Upon a Time in Hollywood, for which he won an Oscar. This year DiCaprio is again nominated in Best Picture-favourite One Battle After Another, and will no doubt show up in his Armani tuxedo as he did at the 2020 Oscars below, looking like the movie star he is.  —Staff  |  KMazur/WireImage; Evan Agostini/Getty Images
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