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7 of the most iconic celebrity couple fashion moments

This one goes out to you, Bennifer.

by Roisin Lanigan
20 May 2021, 7:00am

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As everyone knows, there is one good thing, and one good thing only, about being a part of a stable and loving relationship. It’s not having someone to whine at when you’re hungover and deep in the Sunday scaries, nor is it getting to avoid the minefield world of dating apps when you fancy a shag, or the slight (ever so slight, tiny really) possibility of owning joint property some day (ah, romance!). No, the most lawfully good thing is when you get to dress up nice together and take couple fashion pics. Everyone knows this. Everyone. 

But of course, nobody does this like the pros. When us mere mortals attempt the matchy matchy fashion moment with our significant other, there’s always a risk of falling short of the chic, Instagrammable romantic moment of synchronicity you crave. Celebrities, though, they know how to nail it. They have truly mastered the art of commodifying their romantic lives and advertising their domestic and sexual happiness through the art of couples fashion. These seven iconic duo outfits prove our point!

1. Bennifer 

The rumours that iconic noughties couple Ben Affleck and Jennifer Lopez, AKA Bennifer, are back together 17 years after they ended their engagement has got us all believing in the miracles of love (and the power of a fit ex). J-Lo has even been sharing love notes on her Instagram story. Cute! We’re most excited about the rumoured reunion though, because Bennifer had some real power couple outfits in their prime. While the tabloid darlings graced many a red carpet in some beautiful gowns and snazzy prom-night style suits, some of their best looks were their more casual attire — Jen in a tight white tank, bell-bottoms and chunky heels, Ben in white and cream, a little dishevelled, baseball hat askew. But their most iconic moment arguably came when they starred in J-Lo’s music video for the 2002 banger “Jenny from the Block”. Jennifer in a hot pink string bikini on the deck of a yacht, while Ben kisses her butt in camo pants and a white tank top? Peak 2002 energy. 

Britney Spears & Justin Timberlake of NSYNC at the Shrine Auditorium in Los Angeles, CA
Photo by Jeffrey Mayer/WireImage

2. Britney and Justin’s double denim

Can you believe it’s been 20 years (two whole decades!) since Britney Spears and then-boyfriend, the lesser-known celebrity Justin Timberlake, reinvented the Canadian tuxedo? Us neither. But yes, it was at the 2001 American Music Awards that Britney at last made denim formal, in a floor-length full jean strapless jean dress, accessorised with a diamond choker, low slung chain belt and some very icy cuffs. And the magnanimous queen that she was and continues to be, Britney let her boyfriend come along for the ride, in a full denim tuxedo, complete with sunglasses and cowboy hat. Inspiring endless Halloween costumes for years to come, the look truly proves that love means lifting someone up to your level, to share in your beauty and success. You’ll get there one day Justin.

3. Shawn Mendes and Camila Cabello

The best fashion choices are ones that communicate a message greater than “jeans and a nice top”. Case in point: the paparazzi images of Shawn Mendes and Camila Cabello, which we can only assume, from their mismatched casual trackies, tie-dye and oversized jumpers, uber-slow pace and empty coffee cups, are a performance art piece for the waiting photographers. Sort of an exercise in dadaism, if you will. The couple is using their joint fame to ask us, the viewer, to truly examine the high cultural importance we place on celebrity. Their clothing choices, so far away from the world of red carpet haute couture, both subvert the image of the celebrity couple, and also draw attention to the quarantine-chic, stay-at-home style we’d all been forced to adopt during the pandemic. A truly groundbreaking piece of theatre. Or they’re just selling couples pics to paps. Honestly, who can say!

4. Brad and Jen (and Gwen!)

It’s been widely noted that Brad Pitt simply loves to matchy match with whatever woman he is currently with. When he was with Angelina, it was all black everything, with long tousled hair. With Gwyneth Paltrow it was Connecticut-chic, pastels and short curtained bangs. And with Jennifer Aniston it was peak 90s minimalism. This shot of the couple, papped as they moved in together in January 1998, is a perfect example. Jen in her orange cargo pants and black tank top, Brad channelling Shaggy from Scooby Doo in complementary khakis and an understated grey tee. They have, even in this off-the-cuff moment, of course — of course! — chosen to match their Matrix-style tiny 90s sunglasses. Ugh, miss them. 

Jennifer Lopez and Sean
Photo by Jeff Kravitz/FilmMagic, Inc

5. J-Lo and P Diddy

Before A-Rod and Ben Affleck, there was P Diddy. Jennifer and Sean spent the turn of the millennium together. During their two year relationship, the pair showed up to a hell of a lot of red carpets looking like they’d just rolled off the set of a deliciously Y2K music video. They even appeared at the 2000s Grammys (when J-Lo wore that iconic green Versace dress) together. Diddy later called it one of his favourite ever fashion moments. “We were just stepping up our game,” he told Entertainment Tonight years later, adding that neither of them realised what a huge cultural moment the dress would become. “It was a great moment for her. She deserves it.” We love a healthy and supportive former partner.

Pamela Anderson and Tommy Lee at the MTV VMAs 1999

6. Tommy Lee and Pam

Some of the best things in life (wine, cheese, all leather outfits) become better with age, and that’s definitely the case for the collective fashion choices of Tommy Lee and Pamela Anderson. When images for the new Hulu show about the couple starring Sebastian Stan, Lily James and Seth Rogen surfaced — showing Sebastian in Tommy’s signature smudged eyeliner and black leather pants, and Lily in Pam’s iconic, matching leather waistcoat — the internet had a mild meltdown. While arguably not appreciated at the time, the Motley Crew drummer and Baywatch star, who were together for three years between 1995 and 1998, are finally getting the credit these looks deserve. Justice, tbh. 

7. Posh and Becks

The entire British monarchy should be abolished and then replaced with this one image and nothing else, and that is all I have to say about that.

7 most iconic outfits