As we approach the Oscars this weekend, it’s always fun to look back at some of the best and most memorable dresses from the past. Over the years at the Oscars, we’ve seen how some stars know how to work it effortlessly and just radiate style and confidence on the red carpet (Cate Blanchett, Nicole Kidman, Jane Fonda) while others have fun with fashion and don’t take it as seriously (Cher, Lady Gaga). And there’s definitely room for both. There are too many great dresses from the past to mention here so I should preface the list by pointing out that these are only SOME of my favourites – I could go on and on about many more.
I’m sure we’re going to see some memorable looks this weekend. And I can’t wait. Because the Oscars red carpet is like the Olympics of fashion for fancy fruits.
Gwyneth Paltrow in Tom Ford (2012)
While she can be painful and the cause for millions of eye-rolls over the years, this Tom Ford dress was unquestionably one of the best dresses in Oscar history. Paltrow stunned with the long and sleek look. The cape was awesome and super dramatic, and it started the cape-dress trend we still see so much of today. The accessories also worked well and I loved that she kept it relatively with a simple diamond cuff and one huge cocktail ring. This is still my favourite red carpet look on Gwyneth ever.
Nicole Kidman (2007) in Balenciaga
Nicole has had many impressive moments at the Oscars over the years. And she killed it in 2007 in this sleeveless scarlet gown with a huge bow tied at the neck by then-creative director Nicolas Ghesquière. I loved the detail around the arms and neck – it looked like metallic leather. Also loved the matching red lips. This was for sure one of Kidman’s biggest red carpet wow moments.
Cate Blanchett in Givenchy Couture (2011)
This Lilac embellished dress in 2011 was a show stopper and suited the actress perfectly. The beading detail was beautiful and interesting and I loved the subtle addition of yellow. It was a romantic dress yet futuristic, which was an interesting dichotomy. Blanchett’s fashion choices often look like they could be in a museum and this was no exception. I CAN’T WAIT to see what wears to the Oscars this year.
Michelle Williams in Vera Wang (2006)
A jaw-dropping red carpet moment. When Williams showed up on the red carpet in 2006 with then partner Heath Ledger, everyone was in awe. The stunning yellow colour. The cut. The hair. Those red lips. This was fashion perfection and a look fashion lovers will never forget.
Julianne Moore in Tom Ford for Yves Saint Laurent (2003)
I loved when Tom Ford was designing for Yves Saint Laurent. It was a unforgetable time in fashion and he created many memorable looks including this chic emerald green gown made especially for Moore. And it’s clear the gown was custom because it suited the actress perfectly. Could that colour have been any better with her red hair? I also loved the matching long emerald chandelier earrings. Such a glamorous look.
Nicole Kidman in Jean Paul Gaultier (2003)
The year she won the Oscar for best actress, she also one the night’s best dressed. I vividly remember talking about this dress in detail with a friend. The draping was stunning. And it moved so beautifully. I loved subtle sheerness and how the three straps on the left shoulder came together at the front. It was a timelessly elegant dress and also super interesting. Another memorable fashion moment for Kidman.
Marion Cotillard in Jean Paul Gaultier (2008)
Who could forget Cotillard’s sequin, scaled halter dress she wore the year she won an Oscar for best actress. It was a stunning memorable dress achievement. This is fashion. What I love about a dress like this is that it while it was beautifully constructed, there’s a sense of humour behind it and it helped demonstrate Cotillard’s playful personality. The old school Hollywood hair and makeup also worked perfectly with the modern / fairytale-like gown.
Zoe Saldana in Givenchy (2011)
Saldana gets fashion and knows what it takes to make a statement. She showed off her progressive taste in this layered ruffled purple gown in 2011. The sparkly beaded top was striking and was an interesting juxtaposition to the complicated lower half of the dress. She was wise to keep the hair, makeup and accessories simple because this dress definitely stood on its own. It was a brave choice but it paid off. This was a cool and unforgettable Oscar look.
Charlize Theron in Dior Haute Couture (2013)
Theron’s two piece Dior in 2013 was sooo chic and good looking. It was super simple yet glamorous – what I called at the time “refined elegance.” The fit was outstanding. And it’s hard to tell in photos but the top was beaded so it had a subtle sparkle. Her pixie haircut also contributed to such a great and fresh red carpet look. She also wore incredible vintage Harry Winston diamond bracelets, totalling more than 110 carats, and they were definitely fancy.
Sandra Bullock in Alexander McQueen (2014)
The cut of this gown was incredible. Loved the draping around her hip – such a timeless and classic look. And I loved that it was McQueen. A movie star could have worn this dress in the 50s and it looked just as beautiful on Sandra as it would have back then. Also, like my stylist friend said, if you’re going to go dark, that shade of midnight blue was a cool way to do it as opposed to going with solid black. One Bullock’s best red carpet looks ever.
Lupita Nyong’o in Prada (2014)
That year’s best supporting actress winner’s custom “Nigerian blue” Prada dress was lovely – feminine and reminiscent of a fairy tale. It also moved beautifully. The pleats were unforgettable and had a massive impact as she walked on stage to accept her award. It was a memorable look fitting of the talented and refreshing star.
Rosamund Pike in Givenchy Haute Couture (2015)
The Gone Girl star definitely impressed with this incredible floral applique Givenchy number in 2015. Red dresses can be hard on the red carpet but this one was killer. It was a powerful dress and one that exuded confidence. The cut was masterful and also super flattering. I loved the tied-back hair because it was all about the dress.
Nicole Kidman in John Galliano for Dior (1997)
Finally, no “Best Dresses at Oscars” list is complete without mentioning Nicole Kidman’s chartreuse Galliano for Dior dress in 1997 – easily the most famous dress in Oscar history. It was John Galliano’s first couture collection for Dior and was totally legendary. It changed the game for dress expectations at the Oscars. The colour, embroidery detail and fur trim were exquisite (not a word I use very often). This dress was and is what true couture is all about. Apparently there’s a famous story behind this dress about how Kidman flew to Aspen to find the socialite who had already purchased the dress to get special permission to wear it. The kind of story fashion legends are made of…
Casey Wagar 