Traveling the World in Style: Best Celebrity Vacation Outfits
Our second annual list of the most fashionable globe-trotters.

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.

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

David, Ralph, Dylan, and Ricky Lauren
East Hampton, 1977

Lapo Elkann and Shermine Shahrivar
Portofino, Italy, 2016

Jessica Alba
Portofino, Italy, 2012

JFK Jr.
Martha’s Vineyard, Massachusetts, circa 1980s

Gigi Hadid
Italy, 2016

Alicia Vikander and Michael Fassbender
Sydney, 2014

Beyoncé and Jay Z
Hawaii, 2016

Cara Delevigne
St.-Tropez, France, 2014

Prince William, Princess Diana, and Prince Harry
Lech, Austria, 1991

Russell Wilson and Ciara with her son, Future Zahir Wilburn
Enumclaw, Washington, 2016

Rosie Huntington-Whiteley and Jason Statham
French Alps, 2013

Gwen Stefani
Mammoth Lakes, California, 2014

Kendall Jenner
Vail, Colorado, 2016

Diane Kruger
Park City, Utah, 2014

Kate Moss
Courchevel, France, 2010

Katy Perry
Sun Valley, Idaho, 2016

Kate Middleton
Courchevel, 2016

Elle Macpherson
Aspen, 2015

Chanel Iman
Park City, 2014

Dakota Johnson
Aspen, 2015
Become a DEPARTURES VIP
Join our Weekly Newsletter