The Bold, Risk-Taking Oscar Gown Rachel Zoe Can't Stop Talking About

The 2020 awards season has been a blink-and-you'll-miss it experience, having kicked off a little over a month ago but already drawing to a close with the Academy Awards. Despite the rapid fire succession of carpets and events, A-listers have managed to pull off a range of unique and exciting looks. Rachel Zoe's picks from the 2020 Oscars red carpet demonstrate the most elegant choices of the final hurrah. Whether they were wearing dramatic trains or floor-length shimmer, these attendees managed to take classic red carpet mainstays and bring them into decidedly modern territory. "Historically the most timeless carpet of the season, the 2020 attendees put a fresh spin on classic glamour for lineup fit for the new decade."

From Charlize Theron's stunning Dior gown (which featured a super sexy slit) and Penelope Cruz's vintage Chanel masterpiece to Janelle Monáe's buzzed-about Ralph Lauren look and Cynthia Erivo's jaw-dropping Atelier Versace princess dress, there was plenty to get excited about this year. Considering, Zoe spent much of her career on this very red carpet, styling some of Hollywood's biggest celebrities, it's assumed she keeps an eye out annually for standout moments. Ahead, a few of the stylist's favorites that she thinks should go down in Oscar's history.

Charlize Theron in Dior Haute Couture

Nominated for a best actress award for her role in Bombshell, Charlize Theron opted for an asymmetrical Dior gown. "A perfect example of a classic black gown being anything but boring, from the slit to the train to the curved neckline, all finished with her drop necklace, she looks divine."

Brie Larson in Celine

"A floor-length shimmering gown with a coordinated cape can easily age a younger star, but the muted hue and minimal hair and makeup keep this look feeling incredibly modern and fresh. She looked even more breathtaking on stage."

Penelope Cruz in Vintage Chanel Haute Couture

"There is nothing better than a vintage gown that feels every bit as current as something designed this year. I love her simple hair and Mary-Jane pumps; she looks completely at ease and absolutely radiant."

Janelle Monáe in Ralph Lauren

"A full, A-line skirt, long sleeves and a hood! This Swarovski bedecked Ralph Lauren gown is as breathtaking as her opening performance. I love that she added even more drama with a red lip and a bold necklace. The fashion risk certainly paid off and was one of the most daring on the carpet."

Regina King in Atelier Versace

"Regina King's stunning blush gown combined the best of both worlds; a dramatic full skirt and a body-skimming silhouette. The train and structured bodice with asymmetrical strap and shimmering beading shone on the carpet but looked unbelievable on stage when she presented the Best Supporting Actor award to Brad Pitt."

Renée Zellweger in Armani Privé

"While I think she could have easily worn more dramatic makeup, this column is stunning on her, and rounds out her turn on this awards season circuit in a range of refined and sleek ensembles."

Cynthia Erivo in Atelier Versace

"Cynthia brings her personal style to this bold Versace look with the addition of stacks of rings and ear cuffs. I love how she is embracing the glamour of the evening and opted for another dramatic silhouette, complete with thigh slit and embellished bodice."

Rooney Mara in Alexander McQueen

"Another fantastic example of personal style on the carpet. This striking McQueen gown is so intricately detailed, from the structured sleeves to the cutaway design to the sheer, lace panels and tiers. Her sleek hair, simple makeup, and lack of jewelry are perfectly paired back and allow the dress to take center stage."

This article has been updated from its original version.