The Best-Dressed Couples Of All Time

Some couples are good together, and other couples do good together — but then there are those who just look incredible side-by-side. Usually, in the Hollywood spectrum, one half of a duo is the style stand-out, while the other lets their partner shine (Hey, Ellen and Portia! Bey and Jay! POTUS and FLOTUS!). But, every now and then, there is a perfect confluence of complementing style.
Both on and off the red carpet, these 14 couples helped reinvent the way we conceive dressing in tandem, and prove that nothing is better than when great romance and iconic fashion go hand-in-hand.
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Photo: REX USA/ARALDO CROLLALANZA.
Serge Gainsbourg & Jane Birkin
Aside from James Dean, Serge Gainsbourg may be the sole reason that we think smoking a cigarette looks hopelessly cool. And, Jane Birkin is so classic that she has one of the most sought-after bags in the world named after her. This one's a no-brainer.
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Photo: REX USA/Everett Collection.
Jack Nicholson & Anjelica Huston
Jack Nicholson is one of Hollywood's most notorious playboys, being one of the only gentlemen who can successfully wear sunglasses at night. Anjelica Huston is — well, look at her. Unflappable. No wonder her grace, poise, and style led to Nicholson's longest relationship to date.
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Photo: REX USA/Peter Brooker.
Heath Ledger & Michelle Williams
Forgive us if, to this day, this shot is still the go-to image of young, talented Hollywood. It was this Givenchy dress that cemented Williams as a beloved style icon, and Ledger's laid-back Aussie cool will never be forgotten.
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Photo: REX USA/Dezo Hoffmann.
Keith Richards & Anita Pallenberg
Rock-and-roll magic, through and through. Anita Pallenberg's influence — for better and worse — on one of the most stylish bands of all time simply cannot be denied.
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Photo: BEImages/Matt Baron.
Diane Kruger & Joshua Jackson
Okay, every now and again, Pacey Witter's suits could use a good ironing, but he truly understands the power of a good tailor. For her part, Diane Kruger could show up in a burlap sack velcroed together, and it'd be the chicest ensemble around.
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Photo: REX USA/Stewart Cook/Rex.
Javier Bardem & Penelope Cruz
To be fair, we aren't totally sure if they are on this list because they are perfectly attired, or if they are just the best-looking couple to ever exist, but either reason, these two are always a treat to see on the red carpet.
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Photo: BEImages/Gregory Pace.
Neil Patrick Harris & David Burtka
To be honest, one half of the NPH/DB duo is always perfectly on-point, while the other is often a detail or two shy of hitting the target. The best part? They trade off who gets to be at 110% and who is at 90%. (The exception to this, of course, is this photo, where NPH's swagger is matched only by Burtka's incredible cuffed denim.)
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Photo: BEImages/Matt Baron.
David & Victoria Beckham
Ladies and gentleman, introducing the King and Queen of England.
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Photo: REX USA/Tim Rooke/Rex.
Olivia Palermo & Johannes Huebl
A bit of the new garde, these two constantly head up international best-dressed lists the world over. In fact, he may be one of the only men around who can keep up with Palermo in the sartorial department.
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Photo: REX USA/SNAP/Rex.
Warren Beatty & Julie Christie
Warren Beatty was a specific generation's Ryan Gosling: Unbelievably attractive and representative of the era. Julie Christie was just a style bombshell. 'Nuff said.
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Photo: REX USA/JABPromotions/Rex.
Colin Firth & Livia Giuggioli
When we grow up (clock is ticking), we'd love to be as put-together as Livia Giuggioli. Not just because of her take on well-heeled dressing, but also because of her husband — the Academy Award-winning, professional suit-wearing, handsome Colin Firth.
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Photo: REX USA.
Ali MacGraw & Steve McQueen
True story: When we began writing this post, we started thinking about Love Story, and then we had to watch the whole thing again because of MacGraw's master class in collegiate dressing. One of the most fashion-forward celebs of the late sixties (due to the influence of Diana Vreeland), MacGraw and her husband Steve McQueen were a quintessential American couple — but one whose allure lasted far longer than their relationship itself.
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Photo: REX USA/ARALDO DI CROLLALANZA.
Johnny Depp & Vanessa Paradis
There was some consternation in the office. "Winona!" some declared. "But Kate!" others protested. Yet, it was the decade he was with Paradis that Depp truly mastered his iconoclast style — and Paradis took her own high-fashion knowledge to the red carpet.
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Photo: REX USA/Everett Collection.
Mick & Bianca Jagger
Mick and Jerry, Mick and L'Wren, Mick and Marianne. They are all incredible couples, but none encapsulated that perfect, rock-star cool of Mick and the edgy glamour and sexuality of Bianca.
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