The A-List Group Holidays We Didn’t See Coming

random celebrity holidays

by Katie Rosseinsky |
Published on

Summer, the season of the Instagram holiday humblebrag, is in full swing. Our feeds are saturated with Aperol spritzes (carefully edited in Huji Cam to amp up the orange), beach sunsets, Portuguese tiles and other people's country weddings, but if there's one genre of post that can reliably cut through the Valencia-filtered noise to grab our attention, it's what we fondly refer to as the randomly generated celebrity holiday snap. You surely know the sort of picture we're talking about here: a seemingly arbitrary selection of A-listers (a minor royal here, a former One Direction star there, with an unexpected guest appearance from Bono), happily posing in front of an idyllic backdrop. Did they know each other 24 hours before this photo was taken? Possibly not. Will they now all be best friends forever, and recreate said photo every summer? Possibly, yes.

In the rarefied world of the random celebrity group holiday, there are seemingly two major players: fashion designer Diane Von Furstenberg, the host, and Karlie Kloss, everyone's guest of choice. Those two aside, it's almost impossible to predict what new iterations each summer weekend might bring. Woody Harrelson, Isla Fisher and Matthew McConaughey on holiday with Madonna's impeccably well-connected manager? Sure. Bradley Cooper and Marnie from Girls? Why not! Harry Styles on a yacht? A perfect content opportunity! The only rule is the more, the merrier: surely the end goal is to eclipse the star power of Ellen deGeneres' famous Oscar night selfie.

While we while away the heat wave thinking about the unseen politics of these star-studded group selfies (what happens if someone's eyes are closed? Who gets dibs on the first upload?), here are some of our favourite unexpected holiday-mates...

The best celebrity group holidays, as documented on Instagram...

Gallery

Unexpected Celebrities On Holiday Together

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CREDIT: Instagram @therealdvf

Karlie Kloss, Harry Styles and Diane von Furstenberg

We can only hope that Harry and Karlie had extensive discussions of the relative merits of 1989 versus Red while wearing their his-and-hers white tees.

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CREDIT: Instagram @guyoseary

Isla Fisher, Chris Rock, Bono, Sasha Baron Cohen, Woody Harrelson, Matthew McConaughey

Does this holiday selfie, posted by Madonna's manager Guy Oseary, have more star power than Ellen's Oscar selfie? Discuss.

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CREDIT: Instagram @therealdvf

Irina Shayk, Bradley Cooper, Anderson Cooper, Allison Williams

For further proof that Diane von Furstenberg is the ultimate A-list holiday fixer, here's a snap from last year's star-studded jaunt.

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CREDIT: Instagram @derekblasberg

Justin Theroux, Sienna Miller, Emma Stone, Laura Harrier, Derek Blasberg

A very A-list gathering in the South of France, while also channeling the spirit of promo pictures for '90s pop bands.

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CREDIT: Instagram @karliekloss

Ellie Goulding and Karlie Kloss

Karlie Kloss. On a quad bike. With Ellie Goulding.

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CREDIT: Instagram @mishanonoo

Ellie Goulding, Karlie Kloss, Misha Nonoo, Princess Beatrice

Their extended gang included Ellie's now-fiancé Caspar Jopling, Karlie's now-fiancé Joshua brother-of-Jared Kushner, Meghan Markle pal Misha Nonoo and a bona fide royal, Princess Beatrice.

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CREDIT: Instagram @mishanonoo

Paul McCartney, Misha Nonoo, Karlie Kloss

Why yes, that is ex-Beatle Paul McCartney inexplicably enjoying a yacht holiday with Misha Nonoo, Karlie Kloss and their respective significant others.

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