18 Outstanding Celebrity Date-Night Looks From the ’90s To Now

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Just like their wardrobes, their weddings and their workout regimes, a famous person’s dating life is an endless source of fascination for the general public – especially when the person they’re stepping out with also happens to be a celebrity. The best bit? The outfits. 

Icons of nostalgic date-night style include erstwhile couple Brad and Gwyneth, who slouched their way through the mid ’90s in matching blue jeans and chunky sweaters, and David Bowie and Iman in their complementary tailoring. More recently, Rihanna and A$AP Rocky’s fashion choices for their (frequent) trips to Giorgio Baldi have filled countless column inches. 

Not all of these love affairs lasted, but the looks – like Linda Evangelista’s chainmail Versace minidress – live on. 

Steve Allen


This former power couple lived in his-and-hers leather jackets and denim when they weren’t on the red carpet. Richard Gere’s laid-back jeans and sports jackets allowed supermodel Cindy Crawford to shine – especially when she wore a metallic gold micro mini.

Ricky Vigil M


Tempting as it is to revisit their matching motorcycle leathers, or David’s sarong, the Beckhams’ modern date-night style is their most aspirational. En route to dinner at Harry’s Bar during London Fashion Week, Posh was her own best ambassador in ’70s-inspired clashing prints from her spring/summer 2020 collection, while David dressed down his suit with a white tee and trainers. 

Martin Fraser


Calling all indie sleaze fans: former couple Alexa Chung – seen here giving her girlish coat and Mary-Janes a hit of rock ’n’ roll with deceptively careful use of kohl – and Arctic Monkeys frontman Alex Turner were prom king and queen of the era. 

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Much has been written about Carolyn Bessette-Kennedy’s minimalist style – it remains an obsession on Instagram, a platform invented more than a decade after her untimely death, to this day – but John F Kennedy Jr dressed with as much flair as his wife. His classic tux, combined with her perfectly understated crisp white shirt and black column skirt, made them easily the most dazzling couple at a Whitney Museum benefit in 1999. 

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If a look could have gone viral in 1994, this one would have. When Liz Hurley accompanied Hugh Grant to the premiere of Four Weddings And A Funeral wearing a slit-to-the-thigh Versace dress held together with gold safety pins, she became an instant star. Hugh looked nice too. 

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In their matching biker jackets, Drew Barrymore and her teenage sweetheart Balthazar Getty epitomised the grunge aesthetic that would go on to rule the decade. 

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Lisa Bonet: perhaps the only woman in the world who could make a top hat look effortless. And in then-husband Lenny Kravitz, she found the only man in the world who could match her cool factor. Who wouldn’t tip their chapeau to these two?

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All eyes were on the newly-engaged Jodi Balfour and Abbi Jacobson at the premiere of Prime Video’s A League of Their Own, which Jacobson co-created. Balfour, who played Jackie Kennedy in The Crown, chose powder-pink Old Céline for the occasion. 

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Not only did long-ago lovers Brad and Gwyneth start to look alike when they were a couple – all dirty blonde locks and defined jaws – they dressed alike too. And why wouldn’t you, if you looked this good together in matching blue jeans?

Pepe Mendez


How do sexy French couples do date night? In Jacquemus, bien sûr! Strolling hand in hand in Cannes during the film festival in May, Vincent Cassel’s muted look chimed perfectly with wife Tina Kunakey’s bleached-out separates. Special mention goes to the splash of colour provided by her powder-blue clutch.  

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Behold, preppy date-night style done right by one-time couple Matt Dillon and Cameron Diaz. Matt’s clean-cut chinos complement Cameron’s swingy ponytail and loafers perfectly. 

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This was pre Sex and the City, but Pat Field would surely have approved of SJP’s explosion of curls and simple shirt, unbuttoned just so to reveal a glimpse of skin. 

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Rihanna’s barely-there The Attico coords were emblematic of her loud and proud maternity style – as well as an undeniably hot date-night look. 

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To join George at a Celebrity Fight Night Gala in Italy in 2014, the future Mrs Clooney gave the world a glimpse of what was to come from her red-carpet wardrobe, in a strapless black gown that put the emphasis firmly on glamour. 

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Has there ever been a cooler couple than the king of androgynous style, David Bowie, and his supermodel wife, Iman? Here they are at their enigmatic best at a gallery opening in New York in 1990. 

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We should have known a wedding was on the cards. Snapped at the Venice Film Festival with her exceptionally dapper old flame on her arm, the only thing brighter than J Lo’s bridal white gown was her smile. 

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Looking back now, photographs of Linda Evangelista’s relationship with Kyle MacLachlan serve as a sort of time capsule of hedonistic ’90s fashion. Here, Linda kept her sensational chainmail Versace minidress on to party with her beau at Paris Fashion Week – a look Dua Lipa would surely give her right arm for. 



Zendaya and Tom Holland established themselves as power players on the couple’s style scene with this chic New York outing. Looking try-hard is always a downer on date night, and Zendaya’s “dress” – a belt over an oversized boyfriend shirt – was the opposite. 

This story was originally published on Vogue UK

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