The best Oscar dresses of all time: Editors’ picks

Halle or Jennifer? Gwyneth or Björk? The editors of <em>Hello! Canada</em> and <em>Flare</em> got together to bring you our all-time favourite Oscar red-carpet looks. See why these Hollywood stars and styles won our hearts!
<strong>Penélope Cruz in Balmain, 2009</strong><br><br>The Spanish actress always makes elegance look effortless. But she did so especially at the 2009 Academy Awards, where she wore vintage Balmain – a “frothy ivory confection,” as the <em>Chicago Tribune</em> called it. Besides her simple, sparkling accessories, the only thing Penélope needed to complete her Oscar-night look was a gold statuette, which she promptly collected when she was presented with the Best Supporting Actress trophy for <em>Vicky Cristina Barcelona</em>. “I was saving [the gown] for something very special,” she said before the ceremony. And a special occasion it was.<br><br><strong>Michael Killingsworth @HelloCanada</strong>
<strong>Gwyneth Paltrow in Ralph Lauren, 1999</strong><br><br>The rise of Gwyneth as a bona fide A-lister and my own burgeoning sense of style happened to converge at the height of the 1990s, so the pink Ralph Lauren gown she wore to the 1999 Academy Awards will always be the most memorable. The spaghetti straps! The starchy taffeta! The matching shawl! It’s all so perfectly ’90s and exactly what I dreamed of wearing to prom. Gwyneth recently revealed that she saved the gown for her daughter Apple, although she conceded it may require some adjustments: “Maybe she’ll do a <em>Pretty in Pink</em> thing and resew it!”<br><br><strong>Charlotte Herrold @FLAREfashion</strong>
<strong>Halle Berry in Elie Saab, 2002</strong><br><br>I remember watching the 2002 Oscars and my mum and I literally gasped when we saw Halle’s dress. It managed to be daring and different and so incredibly beautiful all at once. While the <em>Monster’s Ball</em> actress paired the Elie Saab net dress with sparkly rings and big stud earrings, she also had one hidden accessory: an antique emerald ring, given to her by her acting coach, that she carried in her purse for good luck. Clearly it worked: that was the night she became the first woman of colour to win the Oscar for best actress.<br><br><strong>Ishani Nath @FLAREfashion</strong>
<strong>Cher in Bob Mackie, 1988</strong><br><br>Equal parts showmanship and skin, this bedazzled bikini of an Oscar gown is quintessential Cher. It’s everything a good Dark Lady look should be: flamboyant and unspeakably sparkly. The showgirl headdress she wore two years earlier in 1986 (also a Mackie) may be better remembered, but this look is more important in the Cher canon: it’s the night she won her first – and only – Oscar, for <em>Moonstruck</em>.<br><br><strong>Russ Martin @HelloCanada</strong>
<strong>Michelle Williams in Vera Wang, 2006</strong><br><br>Michelle did it first, and best, when she wowed at the Academy Awards in this saffron yellow gown paired with a bold red lip. Imitators followed, wearing the yellow dress/red lip combination on the awards-show circuit, but Michelle tops them all. The gown not only proved that bold colour has a place on the red carpet, but classic bridal designer Vera Wang also makes a mean formal gown – and one that tops best-dressed lists to this day.<br><br><strong>Jennifer Berry @FLAREfashion</strong>
<strong>Cate Blanchett in John Galliano, 1999</strong><br><br>The two-time Oscar winner always looks gorgeous on the red carpet. But I will always love the beautiful John Galliano gown she wore to her first ever Academy Awards (and for her first nomination, for <em>Elizabeth</em>). She brought sexy to the back long before it was a trend, with beautiful appliqués of flowers and hummingbirds that looked like tattoos.<br><br><strong>Chris Daniels @HelloCanada</strong>
<strong>Barbra Streisand, 1969</strong><br><br>Not only did the <em>Funny Girl</em> star shockingly tie for Best Actress (with Katharine Hepburn, whose director Anthony Harvey, pictured here, accepted on her behalf), but Barbra also caused quite the stir with what she wore: a sheer sequinned bell-bottomed pantsuit by Arnold Scaasi. The actress and singer wrote years later: “I had no idea when I wore it to receive the Academy Award that the outfit would become see-through under the lights!”<br><br><strong>David Lee @HelloCanada</strong>
<strong>Mila Kunis in Elie Saab, 2011</strong><br><br>I love this feminine prom-dress look on Mila Kunis, mostly because it’s such a contrast to her usual tomboy style. Often pictured in jeans and a tee sitting courtside at a basketball game, Mila was transformed on the red carpet in this lavender chiffon Elie Saab Haute Couture Spring 2011 gown. The delicate tiered lace detailing and grosgrain ribbon waist seemed like a subtle tribute to the transformation she had made onscreen that year, as a ballerina in <em>Black Swan</em>.<br><br><strong>Ava Baccari @HelloCanada<strong>
<strong>Carey Mulligan in Prada, 2010</strong><br><br>When I first saw Carey hit the red carpet in this Prada dress, I thought it was simply an embellished black gown. But when I realized it was actually covered in tiny utensils and tools, I fell in love with it. It’s so whimsical and such a clever way to upgrade an otherwise standard gown. Carey said later that she ended the night by ripping off the little bits of metal and giving them to her fellow attendees. While that is very sweet, I really hope most of this insanely special dress remained intact.<br><br><strong>Tara MacInnis @FLAREfashion</strong>
<strong>Lupita Nyong’o in Prada, 2014</strong><br><br>Everything about this custom-made Prada gown on newcomer Lupita – from the gorgeous pale blue shade to the subtle sparkle to the deep plunge – was just right. She told Ryan Seacrest: “It’s a blue that reminds me of Nairobi, so I wanted to have a little bit of home.”<br><br><strong>Erinn Stewart @FLAREfashion</strong>
<strong>Björk in Marjan Pejoski, 2001</strong><br><br>Red carpets are full of beautiful dresses, but it’s not often you see someone display so much personality and originality. The Icelandic singer’s 2001 look was so iconic that Valentino reimagined it in their 2014 spring couture collection. Her Swan Dress even has its own Wiki page!<br><br><strong>Marko Popovic @HelloCanada</strong>
<strong>Audrey Hepburn in Givenchy, 1954</strong><br><br>No Oscars best-dressed list would be complete without Audrey Hepburn and the demure, ivory lace gown designed, or rather, redesigned by Hubert de Givenchy. Audrey first wore her “lucky dress” in <em>Roman Holiday</em> and asked Givenchy to alter it for the Academy Awards. She won the Best Actress trophy that year and he went on to become her lifelong friend and collaborator.<br><br><strong>Ally Dean @HelloCanada</strong>
<strong>Jennifer Lawrence in Dior Couture, 2013</strong><br><br>Already the face of Dior at 22, Jennifer established her place amid red-carpet royalty (and on the cover of <em>Hello! Canada</em>) in pale pink Dior Couture. Everything was breathtakingly, time-stoppingly perfect: the hair, the makeup, the gown, the trendsetting backwards necklace (by Chopard)! The most endearing moment, though, came when Jennifer tripped on her Cinderella dress on her way to accept the Best Actress Oscar. “What do you mean, ‘What happened?’” she replied to curious reporters after the fact. “I tried to walk upstairs in this dress, that’s what happened!” <br><br><strong>Alison Eastwood @HelloCanada</strong>
<strong>Celine Dion in Dior, 1999</strong> <br><br>While many have just discovered the French-Canadian star's sartorial savvy, from her angelic Stéphane Rolland gown at the 2017 Billboards to a show-stopping Euro tour wardrobe that summer, Celine has always pushed the boundaries when it comes to her style. The 1999 Oscars were no exception, and tongues were wagging out of control as the performer walked the red carpet in her John Galliano suit with Dior by Stephen Jones hat and embellished Ray Bans (which donated money to her cystic fibrosis charity). “I was the only one with pants in a backward suit from Galliano and if I would do this today it would work," the singer told <em>People</em> last year. "It was avant-garde at the time." <br><br><strong>Jessica Pollack @HelloCanada</strong>
<strong>Nicole Kidman in Balenciaga, 2007</strong> <br><br>Nicole looks spectacular in her scarlet Balenciaga gown. It also reminds me of a Street Fighter videogame character named Rose; all the characters in that game are illustrated with so much flair and style. <br><br><strong>Wallace Pei @HelloCanada</strong>
<strong>Marion Cotillard in Jean Paul Gaultier, 2008</strong> <p>This was a natural pick for me (as a huge fan of all things mermaid, both in print and in cut!). The French star's stunning gown was adorned with hundreds of fish-like scales and featured a vintage, Marilyn Monroe-esque neckline. Paired with a modest yet stunning short train and sideswept loose curls, Marion literally transformed into a sea goddess on the red carpet before winning Best Actress for the biopic <i>La Vie En Rose</i>.</p> <p><strong>Meaghan Wray @HelloCanada</strong></p>
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