Best-dressed Oscar couples of all time, from Angelina Jolie and Brad Pitt to Beyonce and Jay-Z

Ahead of the Oscars on Sunday, Olivia Petter looks back at some of the most memorable celebrity couple moments on the red carpet

Sunday 27 March 2022 07:30

Finally, after two years of non-existent red carpets, the Oscars is here to serve up a much-needed a dose of real-life glamour.

On Sunday, the 94th Academy Awards will take place in Los Angeles, and while there are memorable red carpet moments every year at the Oscars, some of the best ones have been when couples walk the red carpet together.

Remember Leonardo DiCaprio and Gisele Bundchen? Or Nicole Kidman and Tom Cruise? Despite the fact many of them have since broken up, there’s nothing quite like commemorating some of Hollywood’s most glamorous pairings from years gone by.

Especially when there are so many celebrity couples you might have forgotten were even together at all, like Jack Nicholson and Angelica Huston, or Sarah Jessica Parker and Robert Downey Jr.

It’s not clear if there will be any stellar couple appearances this time around, we’ll have to wait and see on the night. But ahead of the big event, we’ve rounded up some of the best-dressed couples of all time.

Angelina Jolie and Brad Pitt, 2012

It would be hard not to include at least one photograph of Angelina Jolie and Brad Pitt, who attended the Oscars several times together while they were married - they divorced in 2019.

But this particular appearance in 2012 stands apart from the rest, and that’s mostly due to Jolie’s dress: a black velvet Atelier Versace gown that came with such a high slit, that the actor’s popped-out leg subsequently landed its own Twitter account.

Pitt, meanwhile, opted for a classic tuxedo for the evening by Tom Ford.

Nicole Kidman and Tom Cruise, 2000

Nicole Kidman and Tom Cruise attended the Oscars several times during their 11 years of marriage - they divorced in 2001.

This one stands the test of time mostly thanks to a now-iconic photograph of Kidman leaning her head back and smoking a cigarette at the Vanity Fair afterparty. But it’s also thanks to their stellar ensembles, with Kidman choosing a shimmering gold gown by Dior that she wore with a pair of antique fingerless gloves.

In a recent interview with Entertainment Tonight, the Australian actor said that dress in particular was one of her all-time favourite Oscars looks.

Cruise wore a classic single-breasted tuxedo for the occasion.

Beyoncé and Jay-Z, 2005

The iconic A-list couple, who now have three children together, made quite an entrance when they walked the red carpet together at the Oscars in 2005.

Beyoncé chose a strapless black velvet gown by Atelier Versace for the evening that had a slight train.

She accessorised the look with a pair of dramatic diamond drop earrings.

Jay-Z, meanwhile, chose a black single-breasted suit which he paired with a black velvet bowtie to match Beyoncé’s gown.

Leonardo DiCaprio and Gisele Bundchen, 2005

In 2005, one of Hollywood’s golden couples, Leonardo DiCaprio and supermodel Gisele Bundchen, made a memorable appearance at the Oscars - they split several months later.

It was the first time DiCaprio had brought a girlfriend to the annual awards ceremony. He wore a classic tuxedo for the event, while Bundchen chose a white strapless embroidered gown by Dior.

Ellen DeGeneres and Portia De Rossi, 2014

Ellen DeGeneres is no stranger to the Oscars, remember the iconic selfie she took with a whole host of stars? That was the same night Degeneres was hosting the Oscars, and she attended with her wife, Portia De Rossi.

Both women dressed to the nines that night, with DeGeneres wearing a custom-made suit by Saint Lauren while De Rossi chose an ivory beaded halterneck gown by Naeem Khan.

Brad Pitt and Gwyneth Paltrow, 1996

An unforgettable moment in celebrity history: when Brad Pitt and Gwyneth Paltrow dated in the 1990s.

They attended the Oscars together in 1996, with Pitt wearing an unusual pair of small oval sunglasses with a black three-piece suit, while Paltrow chose a simple white strappy sequin floor-length gown by Calvin Klein.

Heath Ledger and Michelle Williams, 2006

Heath Ledger and Michelle Williams started dating in 2004 after they met on the set of Brokeback Mountain. The couple had one daughter together, Matilda, but split in 2007, one year before Ledger’s death in 2008.

Their memorable Oscars moment came in 2006, when Williams was nominated for Best Supporting Actress in Brokeback Mountain - Ledger was nominated for best supporting actor. She wore a canary yellow gown by Vera Wang for the evening that featured a fishtail hem and a plunging neckline adorned with ruffles.

Williams’ classic Hollywood look was offset by Ledger’s traditional tuxedo.

Pharrell Williams and Helen Lasichanh, 2014

Few couples could pull off this synchronized ensemble (or shorts on the red carpet), but Pharrell Williams and his wife, Helen Lasichanh do so with aplomb.

For the Oscars in 2014, Williams chose a unique short suit by Lanvin with a pair of lace-up brogues and a bow tie. Lasichanh, meanwhile, opted for a pair of skinny black trousers and a white tuxedo jacket with a pussy-bow blouse underneath.

Jennifer Lopez and Marc Anthony, 2006

The former couple, who divorced in 2011, were one of Hollywood’s most beloved couples when they were together.

For the Oscars in 2006, they made a statement on the red carpet in their respective looks, with J Lo choosing a vibrant green ruched gown that was actually a vintage piece by Jean Dessès.

Anthony chose a classic black suit with a white tie.

Anjelica Huston and Jack Nicholson, 1986

This classic Hollywood duo looked the perfect part when they walked the red carpet at the Oscars together in 1986.

Huston chose an emerald green off-the-shoulder gown with a central jewel for the night when she beat Oprah Winfrey to win Best Supporting Actress for her performance in Prizzi’s Honor.

Nicholson, meanwhile, who was nominated for his leading role in the same film, wore a classic tuxedo and a pair of sunglasses to the event.

Justin Timberlake and Jessica Biel, 2017

Justin Timberlake and Jessica Biel are, unlike many of the other couples listed here, still together.

While they have several Oscars red carpet moments to choose one, this is by far the best because of the image itself - Timberlake’s cheeky pose behind his wife offers a rare moment of spontaneity in the Oscars’ formal proceedings - and, of course, Biel’s intricately embellished metallic gown by Kaufman Franco. Timberlake, meanwhile chose a Tom Ford jacquard evening jacket with matching suit trousers and bow tie.

Will Smith and Jada Pinkett Smith, 2006

Another couple that is no stranger to red carpet appearances, and are still married, is Will Smith and Jada Pinkett Smith.

In 2006, Pinkett Smith turned heads in a cobalt blue strapless gown by Roberto Cavalli, while Smith chose an outfit that almost matched his wife’s by wearing a navy blue striped suit.

Sarah Jessica Parker and Robert Downey Jr, 1989

Sarah Jessica Parker made a notable appearance at the Oscars in the 1980s with her then-boyfriend Robert Downey Jr.

The actor chose a simple black velvet cocktail dress with a pearl necklace - a far cry from some of her later red carpet looks, while Downey Jr chose a unique suit with wide lapels a green necktie.

Heidi Klum and Seal, 2008

Before this much-loved Hollywood couple split in 2012, they had many standout red carpet moments. This was one of them, with Klum wearing a scarlet John Galliano gown that featured a square neckline with a hooded back.

Seal complimented the supermodel’s outfit with a traditional black tuxedo and a skinny tie.

Helen Mirren and Taylor Hackford, 2007

The year that Helen Mirren took home the best actress award for her role in The Queen, she packed quite the fashion punch on the red carpet with her husband, Taylor Hackford.

Mirren chose a fairytale-like Champagne-coloured Christian Lacroix gown that featured a pleated skirt and a beaded bodice.

Hackford chose a black suit but wore a metallic-coloured tie to match his wife’s gown.

Cindy Crawford and Richard Gere, 1992

Another memorable celebrity couple from the 1990s is, of course, Cindy Crawford and Richard Gere.

The duo attended the Oscars together in 1992, with Crawford choosing a black sequin gown with a fishtail hem while Gere wore a double-breasted tuxedo.

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