WWD Report Card: The Top 10 Moments of Awards Season

This awards season has been one for the history books. WWD had its doubts, but this has proven to be one of the strongest red carpet seasons in modern history. The relationship between runway and red carpet is closer than ever, and the digital red carpet allowed for greater risk and designers never seen at awards shows before. Men’s wear emerged as the most exciting to watch, with the new leading men changing the rules of evening wear dressing. The result is a whole new class of style stars. Here are WWD’s picks for the most memorable:

Regina King – 5

It was difficult to choose one look from the variety of hits King has had this season, but this custom Louis Vuitton gown is fit for a queen.

Regina King at the 2021 Oscars.

Regina King at the 2021 Oscars.  Chris Pizzello/Pool Via PMC

Cynthia Erivo – 5

Erivo proved that personal style makes all the difference: this Valentino dress looked even better on the carpet than it did on the runway. And those platform shoes are to die for.

Cynthia Erivo in Valentino at the 2021 Golden Globes.

Cynthia Erivo in Valentino at the 2021 Golden Globes.  Todd Williamson/NBC/Courtesy Photo

Dua Lipa – 5

The year of lockdown has also been the Dua Lipa breakout year. Throughout the Grammys night there were several outfit changes, but the red carpet Versace gown is still our favorite.

Zendaya at the 2021 Oscars.

Zendaya at the 2021 Oscars.  Chris Pizzello/Pool Via PMC

Trace Ellis Ross – 5

Schiaparelli rarely makes it onto the red carpet, but was perfect for making an at-home style statement in the hands of fashion star Ross, who turned this into an instant classic.

Tracee Ellis Ross in Schiaperelli and Ana Khouri at the NAACP Awards.

Tracee Ellis Ross in Schiaperelli and Ana Khouri at the NAACP Awards.  Courtesy Photo

Zendaya – 5

Hair blowing in the breeze, long Valentino gown billowing behind her, millions in Bulgari jewelry adorning her — this was the definition of a major moment.

Zendaya at the 2021 Oscars.

Zendaya at the 2021 Oscars.  Chris Pizzello/Pool Via PMC

Leslie Odom Jr. – 5

This was another example of a season full of greatest hits, but the BAFTAs colorful ensemble wins the prize. Odom Jr. was at the forefront of pushing bright-color dressing as the main men’s wear message.

Leslie Odom Jr. in Versace at the BAFTAs.

Leslie Odom Jr. in Versace at the BAFTAs.  Austin Hargrave/Courtesy Photo

LaKeith Stanfield – 5

Never has a jumpsuit looked so good. The ’70s spread-collar shirt and belt detail enhance the V shape of the Saint Laurent look.

Lakeith Stanfield in Saint Laurent at the 2021 Oscars.

Lakeith Stanfield in Saint Laurent at the 2021 Oscars.  Chris Pizzello/Pool Via PMC

Josh O’Connor – 5

His consistent collaboration with Loewe paid off this season, hands down. This brown three-piece suit also channeled ’70s vibes with perfect chic flair.

Josh O'Connor at the 2021 SAG awards.

Josh O’Connor at the 2021 SAG awards.  Courtesy of SAG

Paul Mescal – 5

In some instances, going minimal is the way to go. Mescal’s perfectly tailored black suit with matching Prada tie proved that less can be more.

Paul Mescal in Prada at the 2021 Critics Choice Awards.

Paul Mescal in Prada at the 2021 Critics Choice Awards.  Courtesy of Prada

Chloé Zhao – 5

There are moments in red carpet history when unpredictable choices are what are remembered. Zhao’s knit Hermès dress paired with white sneakers and simple braids were the epitome of effortless cool.

Chloe Zhao at the 2021 Oscars.

Chloe Zhao at the 2021 Oscars.  Chris Pizzello/Pool Via PMC