Our Pick: The Best Dressed Couples At The Oscar Over The Years

The 2021 Oscars happened. There were winners all around, both for acting and style. Unlike other Oscars, attendance was low due to the current pandemic. Only the nominees and a few guests were present.

The glamor of the night is the stuff for Hollywood watchers and fashion enthusiasts over the years. However, it’s not only who wins the coveted prize that captures headlines but also who the stars show up with.

From the iconic appearance of couples like Madonna and Michael Jackson to Angelina Jolie’s Twitter-approved leg pose, the Oscar red carpet over time has seen couples sizzle up the night with their style. Scroll below for the best-dressed couples at the Oscars over the years.

Halle Berry and Van Hunt

How can we start this list without a nod to this year’s Oscars? Previous Oscar-winner Halle Berry made an appearance with her beau Van Hunt and what an appearance it was.

Van Hunt wore a classic tuxedo. However, he switched up the style by wearing all black from head to toe. Standing by his side on the red carpet was the gorgeous Halle Berry, stunned in a cascading, billowy, soft purple gown.

Angelina Jolie and Brad Pitt, 2012

Angelina Jolie and Brad Pitt’s divorce is making headlines at the moment. However, back in 2012, the couple made a stylish appearance at the Oscars. How stylish was the appearance? Well, how about Jolie’s leg gaining its own Twitter Account, stylish.

Jolie and Pitt had made several appearances at the Oscars prior, but 2012 stood out in particular due to Jolie’s black velvet Atelier Versace gown. The actress popped out her leg out of the too-high slit, and the rest made Twitter history.

Ellen DeGeneres and Portia De Rossi, 2014

On the same night that Ellen DeGeneres took one of the most iconic selfies with a host of stars at the 2014 Oscars is the same night she and her wife, actress Portia De Rossi, made a stunning appearance on the red carpet.

DeGeneres wore a glittery all-black tuxedo from Saint Laurent, while De Rossi complemented the talks show host in an embroidered white halterneck gown by Naeem Khan.

Heath Ledger and Michelle Williams, 2006

Michelle Williams and Heath Ledger showed off their star power at the 2006 Oscars. The couple was nominated for best-supporting actress and best-supporting actor for their roles in the critically acclaimed film “Brokeback Mountain.”

The couple had met two years prior on the set of the same film and had one daughter together. On the red carpet, Williams wore a brilliant yellow gown with a fishtail hem and a plunging neckline offset with willowy ruffles while Ledger’s tuxedo paired nicely with William’s look.

Anjelica Huston and Jack Nicholson, 1986

Anjelica Huston and Jack Nicholson were very much the Hollywood ‘It couple’ and made it known at their very dapper appearance at the 1986 Oscars. Both were nominated for their roles in the film “Prizzi’s Honor.”

Huston took home the prize. However, the two were very much the winners of style that night. Huston stunned in an emerald green one-shoulder gown decorated with a jewel at the bust. By Huston’s side, Nicholson wore a polished three-piece suit with a silk sling on his injured hand.

Michael Jackson and Madonna, 1991

Could we have a more iconic duo? The queen and the king of pop made an appearance in what is perhaps the most legendary Oscar moments of all time while dressed to the nines.

Madonna’s style was reminiscent of the golden age of Hollywood Cinema. She wore a sparkly, strapless white Bob Mackie Gown, white gloves, and an equally white furry boa. Jackson wore printed pants and a black and white sequined jacket.

Jason Momoa and Lisa Bonet, 2019

This genetically blessed couple appeared at the 2019 Oscars and turned the heat up with total boho vibes. Bonet and Momoa both wore dusty pink outfits that added a freshness to the red carpet.

Putting up a united front, the couple wore Fendi ensembles, with Bonet dressed in a netted tea-length gown. Moreover, Momoa put a smile on our faces with a velvety blush pink tuxedo that perfectly complemented Bonet.