Just like their wardrobes, weddings, and exercise routines, a celebrity’s love life is an endless source of fascination for the general public — especially when the person they’re dating is also a celebrity. The best part? The clothes.
Nostalgic style icons for date night include former couple Brad Pitt and Gwyneth Paltrow, who in the mid-90s paired jeans with 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 the Italian restaurant Giorgio Baldi, located in Los Angeles, have made headlines.
Not all of these love affairs lasted, but the looks — like Linda Evangelista’s knitted Versace mini dress — live on.
This former power couple lived in leather jackets and jeans when they weren’t on the red carpet. Richard Gere’s laid-back pants and sporty coats allowed supermodel Cindy Crawford to shine – especially when she wore a micro skirt in metallic gold.
As tempting as it is to revisit matching leather looks, the Beckhams’ current date night style is the most aspirational. On her way to dinner at Harry’s Bar during London Fashion Week, Victoria was her best ambassador wearing ’70s-inspired prints from her brand’s Summer 2020 collection, while David wore a suit with a white T-shirt and sneakers.
Calling all fans of the indie sleaze style: ex-couple Alexa Chung — seen here giving her feminine coat and Mary-Janes a rock ‘n’roll flair with the deceptively careful use of the kajal — and Arctic Monkeys frontman , Alex Turner, were prom king and queen at the time.
Much has been written about Carolyn Bessette-Kennedy’s minimalist style — she remains an Instagram obsession to this day, even though the platform was invented more than a decade after her untimely death — but John F Kennedy Jr was so talented at dressing. as your wife. Their classic tuxedo, combined with Carolyn’s perfectly understated white shirt and black skirt, easily made them the most stunning couple at a Whitney Museum benefit in 1999.
If one 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 thigh-high Versace dress secured with gold safety pins, she became an instant star. Hugh was also handsome.
In their matching biker jackets, Drew Barrymore and her teenage boyfriend Balthazar Getty epitomized the grunge aesthetic that would rule the decade.
Lisa Bonet: perhaps the only woman in the world who could make a top hat look cool. And in then-husband Lenny Kravitz she found the only man in the world that she could match with her accessory.
Former couple Brad and Gwyneth not only began to look alike physically – blond hair and defined jaws – but they also dressed the same way. And why wouldn’t you if you both looked so good together in matching jeans?
How do French couples go out at night? In Jacquemus, bien sûr! Strolling hand in hand in Cannes during the film festival in May, Vincent Cassel’s understated look paired perfectly with wife Tina Kunakey’s faded look. Special mention goes to the pop of color provided by her pastel blue bag.
Please note: preppy date night style by couple Matt Dillon and Cameron Diaz. Matt’s clean cut pants perfectly complement Cameron’s ponytail and loafers.
This was before “Sex and the City,” but Pat Field would certainly have approved of Sarah Jessica Parker’s burst of curls and the simple shirt, unbuttoned only to reveal a glimpse of skin.
Rihanna’s The Attico looks were emblematic of her maternity style — as well as an undeniably hot evening look.
To join George at a Celebrity Fight Night Gala in Italy in 2014, the then-future Mrs. Clooney gave the world a glimpse of what was to come from her red carpet wardrobe in a strapless black dress that firmly emphasized glamour.
Has there ever been a cooler couple than androgynous style king David Bowie and his supermodel wife Iman? Here they are in the best enigmatic style at the opening of a gallery in New York in 1990.
We should have known that a wedding was on the cards. At the Venice Film Festival holding hands with her great longtime love, the only thing brighter than J Lo’s white wedding dress was her smile.
Looking back now, the photographs of Linda Evangelista’s relationship with Kyle MacLachlan serve as a kind of time capsule of ’90s hedonistic fashion. Here, Linda wore her sensational mesh Versace mini dress to party with her boyfriend, during a Paris Fashion Week – a look Dua Lipa would surely wear these days.
Zendaya and Tom Holland have established themselves as a stylish couple with this chic NYC tour. Looking effortful is always depressing for a date, and Zendaya’s “dress” – a belt over an oversized shirt – was the opposite of that.
All eyes were on newlyweds 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 Old Céline pink for the occasion.