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Home / Fashion
Fashion

Traveling the World in Style: Best Celebrity Vacation Outfits

By Tina Gaudoin on March 06, 2017

Our second annual list of the most fashionable globe-trotters.

© Patrick Lichfield/Condé Nast via Getty Images

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Is it really that hard to look good on vacation? Scratch that. Who wants to make the effort to look good on vacation? Surely downtime should be precious time spent away from the stress of our regular 24/7. No makeup, no tie, no suit, and definitely no heels. Celebrity, though, brings with it certain expectations; vacations are in part a brand extension.

These days, the travels of the rich and famous include stage-managed selfies posted for the consumption of tens of thousands of adoring, ravenous global fans. It gets thorny when the paparazzi come into view with their long lenses and their even longer attention spans. So perfecting the art of looking stylish on holiday has long been a celebrity rite of passage. Nail it and you are Cindy Crawford or Marc Jacobs. Get it wrong and, well, it would be churlish of us to name names.

When we began debating our second annual most-stylish list, we kept coming back to one image (above): the boho couple of their day, Talitha and J. Paul Getty Jr., photographed in 1970 by the late Patrick Lichfield (son of Princess Anne, first cousin to Elizabeth II) on the rooftop of their House for the Senses in the warm dusk of Marrakech. “Everyone looks beautiful in Marrakech,” Talitha is said to have commented. She certainly did. Despite the fact that the two were in residence rather than on vacation, Lichfield’s photograph became the picture that spawned a thousand chic vacation shots. We wondered, Could the photo be bettered?

We chose two locations: ski resorts—where looking chic while staying upright (or not) demands herculean efforts—and beach backdrops, where the skimpiest of outfits must be sported with aplomb, grace, and more often than not a great body. Did we get it right? Let us know at depeditors@timeinc.com, but for the moment, sit back and enjoy our second parade of the globe’s most stylish travelers.

 
Bauer-Griffin

Eva Mendes

Aboard Domenico Dolce and Stefano Gabbana’s boat, Portofino, 2009

Photo by Susan Wood/Getty Images

David, Ralph, Dylan, and Ricky Lauren

East Hampton, 1977

Fabio Piumetti / Getty Images

Lapo Elkann and Shermine Shahrivar

Portofino, Italy, 2016

Jessica Alba/Twitter

Jessica Alba

Portofino, Italy, 2012

Tom Wargacki/WireImage

JFK Jr.

Martha’s Vineyard, Massachusetts, circa 1980s

Gigi Hadid/Instagram

Gigi Hadid

Italy, 2016

INFphoto.com

Alicia Vikander and Michael Fassbender

Sydney, 2014

Beyoncé

Beyoncé and Jay Z

Hawaii, 2016

Pierre Suu / Getty Images

Cara Delevigne

St.-Tropez, France, 2014

Julian Parker/UK Press via Getty Images

Prince William, Princess Diana, and Prince Harry

Lech, Austria, 1991

Ciara/Instagram

Russell Wilson and Ciara with her son, Future Zahir Wilburn

Enumclaw, Washington, 2016

Bauer-Griffin

Rosie Huntington-Whiteley and Jason Statham

French Alps, 2013

Terma/SL/FAMEFLYNET PICTURES

Gwen Stefani

Mammoth Lakes, California, 2014

MiamiPIXX/SBMF/FAMEFLYNET

Kendall Jenner

Vail, Colorado, 2016

Alo Ceballos / Getty

Diane Kruger

Park City, Utah, 2014

Bauer-Griffin

Kate Moss

Courchevel, France, 2010

Katy Perry/Instagram

Katy Perry

Sun Valley, Idaho, 2016

Bauer-Griffin

Kate Middleton

Courchevel, 2016

Fame Flynet

Elle Macpherson

Aspen, 2015

Alo Ceballos/GC Images

Chanel Iman

Park City, 2014

Goodwin/Dunkin D/AKM-GSI/FAMEFLYNET

Dakota Johnson

Aspen, 2015

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