The 10 most memorable Oscars fashion moments

With all eyes on the red carpet tomorrow night, Annmarie O’Connor pays tribute to Oscar’s most memorable fashion moments.

The 10 most memorable Oscars fashion moments

With all eyes on the red carpet tomorrow night, Annmarie O’Connor pays tribute to Oscar’s most memorable fashion moments.

From protest outfits to princess gowns, pinstripe suits to perfectly wacky creations, the annual Academy Awards are as much about fashion as they are about film.

This Sunday at Hollywood’s Dolby Theatre, the red carpet will take centre stage for some of the industry’s most unforgettable sartorial moments.

Watched by hundreds of millions of viewers in over 200 countries, even those not nominated to win an Oscar still have an opportunity to become part of a broader televisual legacy.

To celebrate, this the award’s 90th birthday, we look back upon some of the most memorable looks that are still talked about to this day. And the statue goes to…


Halle Berry won big with her 2002 best actress award for her performance in Monster’s Ball. Equally outstanding was her Elie Saab gown featuring a mesh embroidered top. Worn with a fresh pixie haircut and flawless make-up, Berry’s look was the right amount of risqué to be memorable without overshadowing the real star of the night – her 13.5-inch gold statue.


Cher is no stranger when it comes to making a style statement. So, when it came to being overlooked as a nominee for her role in the 1985 hit Mask, the performer knew just the right way to reclaim some of that lost limelight. Her chain-link halter and feather headdress made by outré designer Bob Mackie – a long-time collaborator with the singer-actress – did all the talking.


No one will ever forget this dress. Ever. Icelandic singer Björk probably didn’t anticipate the furore that followed the swan dress she wore to the Oscars in 2001.

Created by Macedonian designer Marjan Pejoski, the avant-garde creation has since become the stuff of fashion history for mixed reasons including the added touch of the artist mimicking laying an egg on the red carpet.


Ms Paltrow’s 2012 Tom Ford cape and gown exemplify the paradox of minimalist chic. The architectural silhouette of the two-piece offset by a razor-sharp bob prove that less is more, even if her Anna Hu rose-cut diamond bracelet (inspired by the Snow Queen in The Nutcracker) weighs in at $1million for its 163 carats. We’ll let that one slide.


It was no surprise when Hilary Swank scored a gold statue for her performance in the 2005 critically-acclaimed film Million Dollar Baby. The vertigo-inducing dip of her backless Guy Laroche sapphire gown did make jaws drop. The demure high neck and long sleeves paired with simple diamond earrings, only served to belie the impact of her toned back amidst 27 yards of silk jersey. The verdict? A pure knock out.


There’s always the danger of looking washed out or like a Big Bird tribute act. Emulating a ray of sunshine needs to look artless which is why Michelle Williams’s tulle-pleated Vera Wang gown gives her that effulgent glow. We just can’t stop looking at her. Those golden locks, the masterful red lip – she makes it look so easy. Now, if only we could do the same.


Borrowing from the boys (and wearing it much better) has always been a Diane Keaton signature. From her eponymous role in Annie Hall to her off-screen fashion nous, the actress is never far from killer tailoring and a bowler hat. The 2004 Academy Awards was no exception when Keaton donned a pinstriped three-piece Ralph Lauren ensemble (complete with wingtips) to grace the red carpet. This, folks, is how it’s done.


2012 will always be known as ‘the year of the leg’ – Angelina Jolie’s right leg to be precise. When the actress’ lithe limb made a bold appearance under a black thigh-slit Atelier Versace gown, it nearly broke the Internet. Not only did @AngiesRightLeg acquire its own Twitter account but ‘legbombing’ became a viral term with Jolie’s gam appearing in hundreds of hilarious memes online.


It’s unsurprising that Ruth Negga’s Pierpaolo Piccioli–designed Valentino dress at last year’s Oscars was inspired by clouds. An ethereal floor-skimming silhouette wrought in commanding red creates the perfect interplay between sophistication and strength, especially when offset by a blue American Civil Liberties Union ribbon (following Donald Trump’s travel ban) and a Jazz Age-inspired headpiece by jeweller Irene Neuwirth. Simply impeccable.


Oh, the controversy surrounding this dress! No ordinary dress, mind you. This custom Calvin Klein dress worn to the 2015 Oscars by actress Lupita Nyong’o boasted 6,000 embroidered pearls and a price tag of $150,000. So, when it was stolen from her Los Angeles hotel room, the West Hollywood Sheriff’s Department was alerted. The dress was found in the second floor bathroom of the hotel, thanks to a tip-off from an anonymous caller.

A great dress deserves a great story.

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