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How the Styles of Ocean's Eleven Cast Have Changed Over the Years

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Aug. 6 2024, Published 1:26 a.m. ET

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It’s incredible to think that the first of the Ocean’s franchise was released over two decades ago in 2001. Of course, this wasn’t the origin of the story. That had come way back in 1960 as a showcase for the original Rat Pack led by Old Blue Eyes himself.

But the reboot, directed by Stephen Soderbergh, more than matched the original for star power. Leading the way were the quartet of George Clooney, Matt Damon, Brad Pitt, and Julia Roberts.

Also in the line-up were Andy Garcia, Casey Affleck, and Hollywood veteran Elliot Gould. It even packed in many cameos from people playing themselves ranging from Lennox Lewis to Angie Dickinson.

As befits a crime caper in which we, the audience, are encouraged to side with the criminals, the Ocean’s cast is nothing if not stylish and cool. For the movie itself costumes were overseen by the Academy Award nominee Jeffrey Kurland but the actors are all notable for having their very own style which has developed over the years.

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They have also appeared in many different movies, in different genres since then, including these titles.

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The Ocean’s movie did a great deal to boost the stars’ profiles. Its Vegas-based setting undoubtedly boosted the popularity of casino games due to the glamor associated with them. There’s no doubt that Vegas was always viewed as the gambling capital of the world but since the success of Ocean’s Eleven in 2001, the gambling industry has undergone some huge changes. Online gambling in particular has shifted dramatically, in Canada, for example, a range of quality providers offer real money slots online to users who can play anywhere at any time of day, this was unthinkable when Clooney, Pitt and co. were starring in the first of the Ocean’s trilogy.

So, how have the styles of the movie’s main stars changed over the subsequent years?

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George Clooney

Clooney has always been held up as one of the suavest, best-dressed actors out there who looks effortlessly stylish whatever he wears. Over the years he has perfected the look of the sharply suited, but casual, matinee idol, even as he has effortlessly moved into middle age.

That’s not to say that he hasn’t also been able to master the formal look when required, attending movie premieres more often than not he’s been seen in smart tuxedos with his glamourous international lawyer wife, Amal, by his side.

At leisure, he has been seen to favor the well-cut linen suit, perfect for relaxing at his holiday home on the banks of Lake Como. For a more rocky and urban style, he’s also at home wearing a leather jacket from favorite designer Georgio Armani.

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Matt Damon

For many years, Matt Damon has played off his boyish looks by dressing to match. When he wore a jacket it was leather, usually accompanied by a beanie hat and a pair of lace-up Doc Marten-style boots.

Even at prestigious events like the Venice Film Festival outfit of choice has always tended to focus on comfort with a classic look being a quality cashmere V-neck over a plain white tee paired with deck shoes and grey cotton trousers.

Recent times have also seen him embracing the silver fox look, especially when attending this year’s Golden Globes where his movie Oppenheimer picked up five awards, though, sadly, none for Damon himself.

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Brad Pitt

Pitt got himself quite a reputation for dressing down even for the red carpet. For example, when he attended the premiere of Mr & Mrs Smith in 2005 it was frayed jeans and a battered leather jacket that he chose. But by 2011 he had started to smarten up his act turning up at the Cannes Film Festival in a salmon-pink suit plus grey scarf and Ray Ban Aviators.

But it was at the Berlin premiere of Bullet Train that he showed that the unconventional was still very much in his DNA when he turned up in a brown midi skirt showing off his leg tattoos.

Julia Roberts

If you want to hear what Julia Roberts’s style is, you can hear it in her own words in an exclusive presentation for Vogue.

If there’s a colour that she’s made all her own over the years it has to be black, whether it’s the elegant full-length evening gown from favourite designer Dolce and Gabbana or the LBD. It’s all a far cry from the outfits she wore in the earlier scenes in Pretty Woman!

So there you have them. The style evolutions of the four main characters from Ocean’s Eleven. Word is that there’s a prequel in the works starring Margot Robbie and Ryan Gosling. So it’ll be interesting to see what Barbie and Ken’s style will be when it hits the big screen.

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