Hollywood's Biggest Night: Three decades of the best Oscar dresses

Hollywood's Biggest Night: Three decades of the best Oscar dresses

On Academy Awards day the movie people spend hours getting dressed up to be judged, most of them probably starving. We are grateful for their sacrifice however, so that we can enjoy doing the exact opposite on any given night from the comfort of our sofas. 

I love a good flick from time to time but the Oscars for me, and maybe you too, is really about the dresses. So until “Best Dress” gets its own award category, I'll be keeping my own history here to share with you.


1993: Cindy Crawford in Hervé Léger

The 90s were for supermodels so kicking off with Cindy Crawford feels right. In 1993, the world's quintessential girl-next-door was married to an actor and dazzled in a white hot Hervé Léger, pioneer of the body con dress, in this aptly named the "bandage" style dress. 

1993 Oscars Cindy Crawford in Herve Legere with Richard Gere


1994: Geena Davis in Ruth Meyers

In a departure from the dress she received much press for just two years earlier, Geena chose a cream colored cross back gown with crystals by British costume designer, Ruth Meyers. It was so lovely and modern and could easily be worn today. I don't think this dress gets enough credit. 

1994 Oscars Geena Davis in Ruth Meyers


1995: Claudia Schiffer in Versace

In the 90s, Claudia's Guess Jeans ads were on the wall of every girl and some boys too I'm sure. When she wasn’t wearing Guess, Claudia, along with most of the other supermodels wore Gianni Versace.  While it's hard to imagine anything not looking good on Claudia, what I loved most about this look is that she wore a matching lavender cardigan which made the whole look seem so sweet.

1995 Oscars Claudia Schiffer in Versace 


1996: Sharon Stone in The Gap

When Sharon Stone showed up in a black turtleneck from The Gap, you sure as heck knew it wasn't a collab back then.

She tells Naomi Campbell in a recent interview about the story behind the choice,

"...it [my Oscar dress] came and the FedEx guy dropped it out of the back of his truck and backed up over it. The box broke open, and the dress had a black tire track down the whole front. The day before the Oscars.”

In pairing her favorite Gap top with a Valentino skirt, she may have been one of the first to mix high and low. Her outfit was celebrated for its chic simplicity and signaled a shift towards more accessible fashion choices, proving that real style is about what you bring to it. 

1996 Oscars Sharon Stone in The Gap

1997: Nicole Kidman in John Galliano

In 1997, Nicole Kidman was a relatively unknown actress. That all seemed to change from this moment onward.

In a chartreuse embroidered chinoiserie gown from Dior, she was one of John Galliano's first major celebrity endorsements after he took the helm at Dior. This moment was pivotal for both Kidman and Galliano, and cemented her status as a fashion icon and his reputation as a couturier capable of reviving the grandeur of Dior haute couture.

The dress's bold color and exquisite craftsmanship were widely praised (except by Joan Rivers) and just like that, the world forgot about who he date was. 

1997 Oscars Nicole Kidman in Dior


1998: Sharon Stone in The Gap and Vera Wang

Lightening seems to have struck twice when Sharon Stone again redefined red carpet elegance. It seemed like a cheeky nod to the everyday woman's wardrobe, elevating a basic white button down shirt from The Gap from ordinary to extraordinary. I don't think she gets the credit she deserved for making the white button down what it is today.  She could wear this today and it would still be a stunning look.

1998 Oscars Sharon Stone in The Gap


1999: Cate Blanchett in John Galliano

For her very first Oscars nomination (as Queen Elizabeth I in “Elizabeth”), Cate Blanchett wore a gown from John Galliano. If someone had described this to me on the phone (because that's all we had back then) it might have been a pass, but thankfully I was not consulted. 

A dark-purple form fitted gown that from some angles appeared almost like denim, flared at the bottom with a a sheer back embroidered with flowers and a hummingbird. She did not win the Oscar but who cares, she won with this dress. Who could have known that this was only just the beginning for Cate and another big win for John Galliano. 

1999 Oscars Cate Blanchett in John Galliano


2000: Cate Blanchett in Jean Paul Gauthier

With Y2K madness firmly in the past, we were excited to get back to the important things.  When someone wins big once, the question always follows if it was intentional or just luck. In this case, it was the former. 

In a streamlined black Jean Paul Gaultier gown accented with gold jewelry a smoky eye, Cate created an unforgettable image that is one of my all time favorites. 

According to Vogue, the jewellery was a last minute addition suggested by her stylist who had just returned from India with the baubles. While we haven’t been able to verify what pieces were an addition vs part of the dress itself, this was certainly an example of when adding more became the absolute right choice. 

2000 Oscars Cate Blanchett in Jean Paul Gauthier


2001: Bjork in Marjan Pejoski

There was only one dress that mattered in 2001 and it belonged to Bjork.  The "Swan Dress" as it came to be known was a dress designed by Macedonian designer Marjan Pejoski. It was a complete departure from traditional red carpet attire and something only Bjork could pull of. If only we had the internet then she would have broke it.

For what felt like weeks, this dress is all people talked about and became an iconic piece of pop culture, symbolizing Bjork's artistic individuality and the blending of fashion with performance art. It was reported that she may have laid up to 6 eggs on the red carpet, a first for the red carpet I'm sure. 

2001 Oscars Bjork in the Swan Dress


2002: Halle Berry in Elie Saab

Halle Berry made history in 2002 by becoming the first African American woman to win the Best Actress Oscar for her role in "Monster's Ball".

Her Elie Saab dress, with its strategically embroidered net top and flowing burgundy skirt, struck the perfect balance between sensuality and elegance.

Elie Saab was quick to credit her for this moment, 

“Halle Berry made the name Elie Saab more popular…she managed to really put the name on the international market. She’s the reason my brand took off.”

2002 Oscars Halle Berry in Elie Saab


2003: Jennifer Lopez in Valentino

The early aughts were peak Bennifer. A bronzed JLo attended the 2003 Oscars in a mint green Valentino gown that paid homage to vintage Jackie O inspired glamour of the 1960s in an elegant one shoulder silhouette with delicate embroidery.

As a multi-talented chamelon she can really work a look and I love seeing the stories she’s trying to tell. The choice was certainly a nod to the timeless appeal of Valentino's designs and her ability to make any look her own. While Ben Affleck came, left, and came back, it's nice to see his facial expressions never left. 

2003 Oscars Jennifer Lopez in Valentino


2004: Charlize Theron in Gucci

When Charlize Theron turned up looking as statuesque as Oscar himself, it had to be a sign. It was certainly a transformation from the one she took on to play serial killer Aileen Wuornous in “Monster", the movie for which she won Best Actress. 

This dress was minimal, elegant glam with a form-fitting silhouette, deep back, and intricate beading. The choice of Gucci highlighted the brand's mastery in combining luxury with cinematic allure, a perfect match for Theron's Oscar-winning moment.

2002 Oscars Charlize Theron in Gucci



2005: Hilary Swank in Guy Laroche

Fashion and Hilary Swank aren’t usually words you hear in the same sentence. Her Guy Laroche choice in 2005 however, seemed to change all that. The navy blue gown was a masterclass in understated elegance, deceptively simple from the front but with a dramatically bold, low back. 

It seemed only fitting that she take home the Best Actress statue for "Million Dollar Baby". 

2005 Oscars Hillary Swank in Guy Laroche



2006: Michelle Williams in Vera Wang

Michelle Williams was a fresh take on the red carpet in saffron yellow Vera Wang.  The deep V-neckline and the flowing silhouette were a departure from more traditional gowns, perfectly capturing Williams's youthful elegance and the joyous nature of her nominated performance in "Brokeback Mountain."

The dress's vibrant color and graceful design stood out in a sea of neutrals, signaling Williams's arrival as a fashion-forward star.

2006 Oscars Michelle Williams in Vera Wang


2007: Jessica Biel in Oscar de la Renta

Not someone I'd expect to see on an Oscars best dressed list but Oscar de la Renta has that effect. In 2007, Jessica Biel won our top vote for this simple pink Oscar de la Renta gown with black belt. The halter-neck design highlighted Biel's great arms and proved again that Oscar de la Renta is always a winning choice. 

2007 Oscars Jessica Biel in Oscar de la Renta


2008: Katherine Heigl in Escada

I think "old Hollywood glamour" is a that gets overused but this is one example of when it could be nothing but. Katherine Heigl wore a red Escada gown, the one-shoulder design reminiscent of styles in the 50s that was both elegant and striking.

Heigl's choice to pair the gown with a matching red lip, classic accessories and a vintage-inspired hairstyle solidified her status as a rising star. I've not seen her around more recently and wonder what she's up to. "My Father the Hero" will always have a special place in our heart. 

2008 Oscars Kathering Heigel in Escada


2009: Angelina Jolie in Elie Saab

Angelina Jolie often wears black and did so in 2009 in a column from Elie Saab. What won us over with this look were the emerald drop earrings that commanded attention without overwhelming. This look was widely praised for its sophisticated simplicity and is probably one of the best examples of statement pieces worn right. 

2009 Oscars Angelina Jolie in Elie Saab


2010: Sandra Bullock in Marchesa

I am still of the belief that Sandra was overlooked by the Academy for her role as the fearless Gracie Hart in Miss Congeniality, I was glad to finally see her recognized for with the Best actress statue for "The Blind Side".

Her Marchesa gown featured beautifully intricate lace and beaded detailing, looking just as good from the back. Paired with a simple hair and minimal jewelry, it was anything but pageant queen. 

2009 Sandra Bullock in Marchesa


2011: Sandra Bullock in Vera Wang

Just when I thought we'd seen the best from Sandra she returned the following year in a knockout red Vera Wang number. A strapless, form-fitting silhouette with a playful bow on the back was beautiful, simple and timeless. 

2011 Oscars Sandra Bullock in Vera Wang


2012: Gwyneth Paltrow in Tom Ford

Many loved the pink Ralph Lauren dress she wore (and apparently wore again just recently) to accept her best actress award in 1999, I did not.

I did, however, love this white hot Tom Ford number she wore in 2012. This cape-draped column was a welcome departure from the more embellished looks that seemed to run rampant that year, showcasing the Goop queen’s penchant for clean lines and sophisticated simplicity. I would have been most scared of spilling something!

2012 Oscars Gwenyth Paltrow in Tom Ford


2013: Charlize Theron in Dior

Back to make another stunning statement this time in a white Haute Couture gown from Dior. The peplum silhouette, combined with a v-cutout neckline and short, pixie haircut, created a look that was both modern and timeless and very difficult to pull off, unless you're Charlize of course. 

Her choice highlighted her statuesque figure and underscored Dior's craftsmanship, proving that that less can be more when it comes to making a lasting impression.

2013 Oscars Charlize Theron in Dior Haute Couture


2014: Lupita Nyong'o in Prada

Lupita Nyong'o captured hearts and headlines in 2014, wearing a light blue Prada gown that appeared to be made of dreams. The deep V-neck and flowing chiffon, combined with her graceful demeanor, evoked a sense of Cinderella magic.

Winning Best Supporting Actress for her role in "12 Years a Slave," Nyong'o's choice of color, inspired by Nairobi skies, was a tribute to her heritage and a perfect reflection of her breakthrough moment in Hollywood.

2014 Oscars Lupita Nyong'o in Prada


2015: Lupita Nyong'o in Calvin Klein

Lupita returned the following year with another show-stopping look, this time in a pearl-adorned Calvin Klein Collection gown. The dress featured over 6,000 pearls and made her again the belle of the ball —and probably very tired by the end of the night. 

2015 Oscars Lupita Nyong'o in Calvin Klein


2016: Cate Blanchett in Armani Privé

If it's possible to be a vision in seafoam then this is it. At this point I believe Cate Blanchett can do no wrong. She attended the 2016 Oscars in an Armani Privé masterpiece adorned with floral appliqués and glimmering crystals.

The dress, much like Blanchett's celebrated filmography, was a blend of craftsmanship and artistry, making her appearance a highlight of the evening and reinforcing her role as a muse within the fashion and film worlds.

2016 Oscars Cate Blanchette in Armani Prive


2017: Viola Davis in Armani Privé

Viola Davis word a vibrant red Armani Privé gown, a choice almost as impactful as her Oscar-winning performance. The bold color and elegant design complemented Davis's grace and celebrated her historic win, making her the first black actress to earn the Triple Crown of Acting winning an Emmy, a Tony and now Oscar. 

Not only a win for Viola, it was another big one for Armani. 

2017 Oscars Viola Davis in Armani Prive


2018: Margot Robbie in Chanel

Before becoming Barbie, Margot Robbie was nominated for her portrayal of ice skater Tonya Harding in "I, Tonya". In 2018 she wore a Chanel Haute Couture gown, an off-white creation, featuring delicate draping and beaded detailing. It was a testament to Robbie's sophisticated taste and her ascent as a fashion icon.

This collaboration with Chanel not only highlighted Robbie's star power but also her ability to embody timeless elegance, balancing her bold on-screen roles with a poised and polished off-screen presence. 

2018 Oscars Margot Robbie in Chanel


2019: Jennifer Lopez in Tom Ford

I love it when JLo does JLo and this dress does not disappoint. The mirror-embellished Tom Ford dress had critics likening her to a disco-ball but when has a disco ball signified anything less than a fabulous time? JLo killed it with this one and she knows it. Now hit the club and celebrate with some Delola girl! 

2019 Oscars Jennifer Lopez in Tom Ford


2020: Renée Zellweger in Armani Prive

All I can say about this choice is that it's just so Renee Zellweger which I mean as the biggest compliment.  I think it was the perfect representation of her personal style—classic, sophisticated, and effortlessly elegant. While seemingly simple, this custom Armani required quite a bit of work which Vogue as created a video about here


2020 Oscars Renée  Zellweger in Armani Prive


2021: Zendaya in Valentino

In a vibrant yellow custom Valentino Haute Couture gown, Zendaya's look was probably the most talked about.  I thought it brought a much-needed burst of joy and optimism to the red carpet. The ensemble, with almost Cher-like hair and completed with Bulgari jewels was a perfect blend of young sophisticate and retro glamour. 

2021 Oscars Zendaya in Valentino 

2022: Zendaya in Valentino

Joining Cate Blanchett and Sandra Bullock as a back to back winner, Zendaya is one to watch.  In a simple two-piece, again from Valentino, a white shirt and skirt combo never looked so good, that is since Sharon Stone wore it in 1998. I'm not sure if this was an intentional nod or just a fashionable coincidence. Either way it was a a big win for the red carpet.

2022 Oscars Zendaya in Valentino


2023: Emily Blunt in Valentino

While I'm curious to know how this dress stayed up all night she certainly pulled it off. Emily Blunt was the epitome of elegance in an impeccably tailored white Valentino gown.  The clean lines and subtle detailing combined with drop earrings accentuated her natural beauty, making a statement that was both understated and impactful. Miranda would certainly approve of this one Emily. 

2023 Oscars Emily Blunt in Valentino

Agree, disagree? 

I look forward to seeing what the 2024 red carpet brings on Sunday March 10th!



After a thorough review of all the looks, our pick for this year was made easy by Carey Mulligan who showed up looking statuesque (no pun intended) and pure perfection in an archival Balenciaga gown. See more photos and details on Vogue

Carey Mulligan in Balenciaga



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