Best and worst dressed celebs on the 2020 Oscars red carpet

From Charlize Theron to Janelle Monae, here's who slayed or dismayed with their outfit choices at the Academy Awards

10 February 2020 - 11:58 By Ricci-Lee Kalish
Singer Janelle Monáe sparkled from head to toe in Ralph Lauren at the 2020 Oscars.
Singer Janelle Monáe sparkled from head to toe in Ralph Lauren at the 2020 Oscars.
Image: Jeff Kravitz/FilmMagic

It's hard to be nominated for an Oscar, and it's even harder to win an Oscar, but what's near to impossible is to do it while looking flawless. The Academy Awards arrivals have always been the pinnacle of what red carpet fashion should be, and this year was no exception.

Here's who slayed and who dismayed with their wardrobe choices at the 2020 Oscars:

Janelle Monáe in Ralph Lauren at the 2020 Oscars.
Janelle Monáe in Ralph Lauren at the 2020 Oscars.
Image: Rick Rowell via Getty Images

BEST DRESSED

JANELLE MONÁE

Singer, songwriter and style icon Janelle Monae dazzled in a bedazzled ball gown covered with more than 168,000 Swarovski crystals. Rumour has it it took the Ralph Lauren team more than 600 hours to make this number. Their work did not go unappreciated.

This futuristic hooded gown is chic and strangely understated in its own haute couture way. It manages to blur the boundaries between fashion and costume without looking like it came out of the fancy dress box  — no easy feat.

From the pop of red on her lips to that diamond necklace, Monae's styling is flawless.

Scarlett Johansson in Oscar de la Renta at the 2020 Oscars.
Scarlett Johansson in Oscar de la Renta at the 2020 Oscars.
Image: Steve Granitz/WireImage/Getty Images

SCARLETT JOHANSSON

The star was nominated in the best actress and best supporting actress categories for her roles in Marriage Story and JoJo Rabbit. She may have lost out on both awards, but she certainly won the red carpet in this Oscar de la Renta gown.

This gown is as demure as it is sexy. It is classy without being boring. We love the fit, we love the colour, and we love the styling. Her golden smokey eyes added extra oomph to a stunning look.

Molly Sims in Zuhair Murad at the 2020 Oscars.
Molly Sims in Zuhair Murad at the 2020 Oscars.
Image: Amy Sussman/Getty Images

MOLLY SIMS

With its exquisitely beaded top and dramatic skirt, this Zuhair Murad gown is a real head-turner.

Having seen it on the runway at haute couture fashion week in Paris earlier this year, we were waiting (and hoping) to spot it on the red carpet this awards season. We couldn't have chosen a better actress to wear it.

The colour of this dress looked divine on Sims, who wisely paired it with nude heels, making her legs look endlessly long.

Spike Lee, pictured with his wife Tonya Lewis Lee, in a custom Gucci suit at the 2020 Oscars.
Spike Lee, pictured with his wife Tonya Lewis Lee, in a custom Gucci suit at the 2020 Oscars.
Image: Rick Rowell/Getty Images

SPIKE LEE

What a beautiful display of brotherhood. Director Spike Lee arrived on the red carpet dressed in the colours of the Los Angeles Lakers as a tribute to the late great Kobe Bryant, who tragically died in a helicopter crash earlier this year. He even had the retried basketball player's jersey number — 24 — appliqued on his lapels and the back of his jacket.

Beyond the touching sentiment, what we love about this custom Gucci look is that it has Lee written all over it. Known for his eclectic fashion choices, he added extra quirk with that over-sized bowtie, hat, orange Nikes, and purple spectacles. 

Natalie Portman in Dior at the 2020 Oscars.
Natalie Portman in Dior at the 2020 Oscars.
Image: Jeff Kravitz/FilmMagic/Getty Images

WORTH NOTING

NATALIE PORTMAN

The actress made a literal fashion statement about the lack of inclusivity at the Oscars by donning a cape edged with names of talented female directors who weren't — and perhaps should have been — considered for the best director category this year. Instead, all the nominees were male.

While we applaud her efforts, and enjoyed the juxtaposition of that masculine cape with that feminine Dior dress, the truth is that without the cape, she probably would have been on our worst-dressed list.

Kristen Wiig in Valentino at the 2020 Oscars.
Kristen Wiig in Valentino at the 2020 Oscars.
Image: Amy Sussman/Getty Images

WORST DRESSED

KRISTEN WIIG

We love that actress Kirsten Wigg took a risk with this Valentino haute couture gown — even if the social media fashion police have been comparing its ruffled edges to lasagna noodles.

We quite like the avant garde nature of its silhouette, but what we hate is those severe black leather gloves. This the perfect example of how bad styling can completely kill a look.

Charlize Theron in Dior at the 2020 Oscars.
Charlize Theron in Dior at the 2020 Oscars.
Image: Steve Granitz/WireImage/Getty Images

CHARLIZE THERON

While attendees such as Wiig may have missed the mark with their fashion risks, at least they tried to stand out. In this overly serious Dior number, Theron just fades into the background.

The mini-peplum on the top did not hit the mark and ended up making Theron look like she has extra-large hips. The severe choice of hair and makeup just solidified this look as a bore fest. Yawn.


Billy Porter in Giles Deacon at the 2020 Oscars.
Billy Porter in Giles Deacon at the 2020 Oscars.
Image: Steve Granitz/WireImage/Getty Images

BILLY PORTER

We adore the actor Billy Porter's gender-bending style choices. He's given millions of people the courage to break the rules and express themselves though fashion.

However, his looks of late (think Grammy's red carpet) have been skewing towards the fancy dress side of things, and this outfit is no exception. When we see costume we see peacocking — a complete red carpet no-no. 

Apparently the designer responsible for this strange sartorial concoction, Giles Deacon, took inspiration from Kensington Palace. We doubt whether they'd let Porter into the palace in this getup.

The structure of the feathered bodice is quite lovely but it's completely at odds with that wild skirt. All in all, there were just too many ideas thrown into one design and they don't gel.

Laura Dern in Armani Prive at the 2020 Oscars.
Laura Dern in Armani Prive at the 2020 Oscars.
Image: Jeff Kravitz/FilmMagic/Getty Images

LAURA DERN

The actress looks like an ice-cream melting on a hot day. The top half of her Armani Prive gown is reminiscent of a bullfighter's costume, and the colour is too harsh a contrast with the soft pink of the bottom.

Sadly, her styling did not help matters. We're all for natural makeup, but the seeming lack of makeup here makes Dern look sallow. Her silver earrings are naff and come out of left field. Simply put, this is a sad, sad look for an evening filled with wonder and excitement.

The 92nd Academy Awards ceremony has come and gone, but not without several memorable moments.The night started with a performance by Janelle Monae, during which she shouted: “It's time to come alive because the Oscars is so white!” Representation was a popular topic of discussion, with many criticising the lack of nominees of colour in acting categories and the lack of female director nominees.