by Megan Bailey, Staff Writer

The Oscars red carpet is my Super Bowl. I live for the drama. Who will win the night? Not the awards, which are also important, but the heavily debated Best Dressed. For the purposes of keeping this list a reasonable length, I’ll be looking at the fifteen best looks from what I’d call the “stylist era” of Oscars fashion, which we are currently still in. Prior to, say, 2005, a good majority of celebrities on the carpet were picking out what they wanted to wear with far less instruction or intervention from stylists. Collaborating directly with designers was also less common, unless you were a household name before you got the invite. This is how you got looks like Celine Dion’s backward tuxedo, Sharon Stone’s Gap turtleneck, and so on. Iconic looks, but of a different time for sure. 

In chronological order, this list is a combination of the iconic, recognizable looks, others that are personal favorites, and notable outfits that bridge the gap between message and fashion. All, I think, will stand the test of time, even if trendiness comes and goes. 

If you’re looking for a comprehensive look at Oscars fashion, I recommend Beyond the Best Dressed by Esther Zuckerman. It’s a really fun review of red carpet looks ranging from the second Academy Awards in 1930 up to 2021, and it’s an interesting reflection on how fashion, Hollywood, and society as a whole have changed over time. Plus, the illustrations are gorgeous.

Keira Knightley, 2006

Keira Knightley was everywhere in 2006, including the Oscars. This Vera Wang dress, while not often seen in Best-Dressed Lists, has always stuck out in my mind. Something about the shade of the dress (is it reddish brown? a wine-ish color?) with that one-shoulder cut and gorgeous Bulgari necklace just works for me. She’s attended the Oscars several times since then, but this is the stand-out look for her.

Michelle Williams, 2006

A look that you will find on most best-dressed lists, Michelle Williams wore this gorgeous mustard Vera Wang gown at the 2006 Oscars. She attended with Heath Ledger, both part of the Brokeback Mountain cast, and she won that evening for Best Supporting Actress. In such a classic dress, it was a perfect moment. The pleated chiffon on the neckline and gathered waist are classic, and the red lip and statement necklace pulled it all together. Truly, this is one for the history books.

Carey Mulligan, 2010

Carey Mulligan broke out in 2009 in An Education, a coming-of-age film about a teenage girl manipulated by an older man. When nominated for the film at the 2010 Oscars, Mulligan looked dressed to kill in this black Prada gown with sparkly appliques and metal scissors and cutlery. Combined with her blonde pixie haircut, this look is edgy, fun, and cute. The appliques and cutlery make what would be a fairly standard gown into something much more visually interesting.   

Mila Kunis, 2011

In 2011, Mila Kunis attended the Oscars as part of the Black Swan cast, and this lavender Elie Saab gown has been burned into my memory ever since. It’s so soft with the lace but sexy with the layering effect and low neckline. The gown pairs perfectly with her dark hair, and I love that she went without a necklace and let the dress do all the work. The other simple accessories let the dress stand on its own, which was a great choice.

Jessica Chastain, 2012

Wearing this black-and-gold Alexander McQueen gown, Jessica Chastain was nominated for Best Supporting Actress in 2012 for her role in The Help. The gold embroidery pops beautifully with her red hair, and the sweetheart neckline is stunning. I’d completely forgotten what movie Chastain was nominated for (thanks, google!), but this dress absolutely sticks out in my mind!

Lupita Nyong’o, 2014

Lupita Nyong’o broke out in 2013, after starring in 12 Years a Slave, and at the Oscars in 2014, she began her red carpet reign. While she has attended the Oscars (and many more award shows) since then, I think this sparkly blue Prada gown is the standout. Accessorizing with a simple headband and bangles, Nyong’o (and the dress) gets to be the star of the show. And the twirls on the red carpet show how truly magnificent the dress is! 

Jenny Beaven, 2016 

Nominated for her costume design in Mad Max: Fury Road at the 2016 Oscars, Jenny Beaven made a bold move, wearing black pants, a black shirt, a striped scarf, and the coolest leather jacket with an Immortan Joe applique inspired by the film. She said, “What I was actually wearing at the Oscars was sort of an homage to Mad Max — a kind of biker outfit.” It was definitely a break from usual Oscars fashion, but one that feels fitting for a costume designer more comfortable dressing other people. She is not the first, and won’t be the last, to wear a look inspired by a nominated film. Notably, in 2018, James Ivory wore a dress shirt with Timothee Chalamet’s face on it when nominated for his adapted screenplay of Call Me by Your Name.

Janelle Monae, 2017

In 2017, Janelle attended the Oscars as part of two major films’ casts: Moonlight and Hidden Figures. As she’d been delivering looks all awards season, I couldn’t wait to see what she’d wear next, and her Oscars look did not disappoint! The Elie Saab gown, with a black mesh top covered in bird appliques and statuesque skirt with mesh sides that match the top, was just dramatic enough to show that Janelle is a fashion force to be reckoned with! Something about this dress is both whimsical and elegant, gorgeous but just this side of weird. She’s since worn more incredible looks, including the hooded silver dress from 2020, but this black one has always stuck out to me.

Chadwick Boseman, 2018

After turning out incredible red carpet looks throughout the Black Panther promotional cycle, Chadwick Boseman attended the 2018 Oscars and did not disappoint. The Givenchy Haute Couture, especially the long jacket, was a standout look in an otherwise relatively boring crop of menswear that night. I give massive credit to Boseman for kicking off the recent trend of interesting looks for men on the red carpet. Notably, his Met Gala 2019 look was incredible as well. I’m both saddened by Boseman’s untimely death and grateful for the incredible work he left behind.

Betty Gabriel, 2018

Starring in 2017’s Get Out, Betty Gabriel attended the Oscars in a truly stunning Tony Ward gown. The blue color, plunging neckline (and back!), and floral appliques all create a memorably gorgeous look for Gabriel. And the dress even has pockets! Everything came together beautifully, and it’s one that I (and probably many others) will remember for years to come.

Rita Moreno, 2018

In 1962, Rita Moreno wore a gorgeous boatneck gown to accept her Oscar for her work in West Side Story. The dress was made in the Philippines, and she’d held onto it until 2018, when she wore an altered version to the ceremony. It appears that the top half of the dress was replaced with a velvet fabric, and Rita wore elbow-length gloves and statement jewelry to complete the look. The silhouette is timeless, and Rita rocked the updated version just as well as she wore the original back in the ‘60s.

Selma Blair, Vanity Fair party 2019

This is the only look not from the Oscars red carpet, but I promise it’s for a good reason. In 2019, Selma Blair wore an incredible Ralph & Russo gown to the Vanity Fair Oscars party, but most notably, the look also included her (regal as hell) cane. She revealed her multiple sclerosis diagnosis in 2018, but this red carpet was her first appearance in Hollywood since then. In the black and pastel dress with matching cape, Blair looked incredible while showing the world who she is. No better look than that! 

Stephan James, 2019

Even though he was snubbed for his role in If Beale Street Could Talk (as was the movie as whole, earning only 3 nominations), Stephan James still turned heads in this gorgeous red velvet suit at the 2019 Oscars. The Etro suit with vest and wide lapels is such a standout look, and I greatly appreciate it, especially now that men’s red carpet fashion is starting to get a bit more interesting. The white boots and pin on his lapel made for great choices to complete the look.

Billy Porter, 2019

Also in 2019, Billy Porter wore the hit look of the night, this tuxedo-inspired gown by Christian Siriano. Breaking gender norms, and looking amazing while doing it, has become a regular occurrence for Porter, but this first look is his best so far. The well-tailored jacket and billowing skirt made a striking silhouette, and Billy carried the look perfectly. As mentioned in the previous entry, men’s red carpet fashion is becoming more and more interesting, and I hope this trend continues!

America Ferrera, 2020

Attending the Oscars in 2020 as part of the How to Train Your Dragon cast, America Ferrera wore a show-stopping cranberry gown and gold headband. The Alberta Ferretti dress and custom Jennifer Behr headpiece are beautiful on their own and even more meaningful with her description. She said, "Tonight, I bring my own warrior ancestors with me, the indigenous Lenca tribe of Honduras." Several months’ pregnant at the time, her dress is a beautiful marriage of comfort, message, and elegance.