While Malia Obama has been living her best life in New York—dining at Soho spots like Café Select and Emilio’s Ballato, interning for the Weinstein Co., partying with Lena Dunham and Jenna Lyons—her parents have been taking their own gap year across the Atlantic, venturing across Italy without political obligations. Earlier this week, Barack and Michelle Obama were spotted in the small Tuscan town of Montalcino, roaming the ancestral homeland of good wine, high art, and olives. (Nearby Florence might get all the attention for its historic galleries of Renaissance art, picturesque plazas, and excellent food, but Montalcino is really where the vineyards get good.)
The former first lady always cuts a chic silhouette, even when dressing for a state dinner or international audience. While in the White House, she worked with her aide Meredith Koop to select looks for each event, choosing labels and pieces with both geopolitical and sartorial resonance. She was an early adopter of designers like Brandon Maxwell and Jason Wu, for whom her stamp of approval proved a massive boon; for the Obamas’ final state dinner, with Italian prime minister Matteo Renzi and his wife, she wore spectacular Atelier Versace. But in Italy, she has cut loose, adapting her already canny sensibility for vacation.
Her wardrobe, which has consisted largely of open-shouldered tops and trousers, demonstrates Michelle is truly, finally, deservedly off duty. While the internet set itself ablaze when she appeared for a portrait in a sleeveless dress near the beginning of her husband’s tenure—how scandalous—on this vacation, she answers to no one. She caused a bit of an internet furor yet again in Italy, albeit a more appreciative response: Her open-shouldered, lace-up white Club Monaco top, paired with BCBG cargo pants and an Elizabeth & James cuff, was both on trend and a departure from her more staid White House looks.
It’s actually quite a daring ensemble, slouchy and revealing. She might just as well be heading for the beach as a touristing excursion around Italy. Whatever the occasion, she’s in consummate vacation mode.
Her next Tuscany look was a one-shouldered pink blouse by the Finnish designer Teija, a Burberry alum, paired with cropped white pants. (The top is already almost sold out, proving the Michelle fashion effect hasn’t been diluted since she departed the White House.) She stopped for gelato—chocolate—and wandered through the narrow cobbled streets as passersby whipped out their phones to capture a rare sighting of Michelle post-D.C.
Michelle Obama Might Be the Best Dressed First Lady Since Jackie O
Michelle Obama in Alexander McQueen at a state dinner in Washington, D.C., January 2011.
Michelle Obama in Azzedine Alaïa in Baden-Baden, Germany, April 2009.
Michelle Obama in Ralph Lauren in London, England, May 2011.
Michelle Obama in Michael Kors on The Tonight Show with Jay Leno, January 2012.
Michelle Obama in Thom Browne at President Obama’s second inauguration in Washington, D.C., January 2013.
Michelle Obama in Carolina Herrera at a state dinner in Berlin, Germany, June 2013.
Michelle Obama in Marchesa at the White House Correspondents Dinner in Washington, D.C., May 2014.
Michelle Obama in Bibhu Mohabaptra at the Congressional Black Caucus dinner in Washington, D.C., September 2014.
Michelle Obama in Zac Posen at the BET Black Girls Rock! special in Newark, New Jersey, March 2015.
Michelle Obama in Mary Katrantzou in London, England, June 2015.
Michelle Obama in Christopher Kane in London, England, June 2015.
Michelle Obama in Carolina Herrera at the arrival of Pope Francis in Joint Base Andrews, Maryland, September 2015.
Michelle Obama in Vera Wang at a state dinner in Washington, D.C., September 2015.
Michelle Obama in Tanya Taylor in Washington, D.C., March 2016.
Michelle Obama in Jason Wu at a state dinner in Washington, D.C., March 2016.
Michelle Obama in Carolina Herrera arriving in Havana, Cuba, March 2016.
Michelle Obama in BCBG at the opening ceremony for the Invictus Games in Orlando, Florida, May 2016.
Michelle Obama in Naeem Khan at the Nordic state dinner in Washington, D.C., May 2016.
Michelle Obama in Hugo Boss speaking with Oprah in Washington, D.C., June 2016.
Michelle Obama in Marni in Monrovia, Liberia, June 2016.
Michelle Obama in Proenza Schouler in Marrakech, Morroco, June 2016.
Michelle Obama in Peter Pilotto in Marrakech, Morocco, June 2016.
Michelle Obama in Proenza Schouler arriving in Madrid, Spain, June 2016.
Michelle Obama in Preen in Madrid, Spain, July 2016.
Michelle Obama in Christian Siriano arriving at a memorial for police officers killed in Dallas, Texas, July 2016.
Michelle Obama in Christian Siriano at the Democratic National Convention in Philadelphia, Pennsylvania, July 2016.
Michelle Obama in Brandon Maxwell at a state dinner honoring the first family of Singapore in Washington, D.C., August 2016.
WASHINGTON, DC – SEPTEMBER 08: First lady Michelle Obama speaks during the President’s Committee on the Arts and the Humanities poetry reading to honor student poets at the White House, September 8, 2016 in Washington, DC. The first lady honored five students with the nation’s highest honor for teen poets presenting original work. (Photo by Mark Wilson/Getty Images)
Michelle Obama in Naeem Khan at the Phoenix Awards dinner in Washington, D.C., September 2016.
Michelle Obama in Self-Portrait at the Broadway Shine a Light event in New York, New York, September 2016.
Her husband got all the attention during their yachting jaunt earlier this year, hobnobbing with his close personal friends like Bruce Springsteen in Tahiti and kitesurfing in the Caribbean with billionaire Richard Branson.
But in Italy—not that it’s a competition—it’s Michelle’s show. (Barack, for his part, has loosened up his collar, foregoing a tie and jacket.) Michelle Obama is, at last, off duty and doing the most—at least for now.
How to Jet Set Like Barack Obama
For one of his most high-profile, post White House appearances, the former president went kitesurfing in the Caribbean with Sir Richard Branson. Sure beats watching a James Comey hearing.
Obama is reportedly staying at Marlon Brando‘s private resort at the Tetiaroa atoll in French Polynesia. Brando fell in love with Tahiti while filming his 1962 movie Mutiny on the Bounty and then bought the resort. The 35-villa resort is known for its celebrity clientele, breathtaking white sand beaches, and its commitment to sustainability. Not a bad spot to work on those memoirs.
Villas at The Brando resort, where Obama is reportedly staying, start at around $2,000 a night. Each villa has its own private beach area and plunge pool, making it perfect for couples, like the former president and the stylish former First Lady Michelle Obama.
Right after President Trump’s inauguration (and a quick trip to Palm Springs), the Obamas flew off to Sir Richard Branson’s private Caribbean retreat, Necker Island. They went kitesurfing and yachting with Branson, and enjoyed some well-deserved vacation time here. Typically, you need to book out the whole island (up to 34 people for $80,000 per night) to stay here, but, you know, he’s the former leader of the free world. Check the website to find one of the individual rooms that occasionally become available.
Between the water sports (sailing, paddleboarding, stand up paddle polo), spa treatments, and daytime excursions, Necker Island is a lifetime removed from Washington D.C.
Doesn’t Obama look happy? Doesn’t he look ecstatic to no longer have to hear the phrases filibustering or congressional hearing on a regular basis? What’s that noise? Sorry, it’s hard to hear all the way up here as you’re kitesurfing above the Caribbean, which just happens to be one of the must-do activities on Necker Island.
Obama played a round of golf at Mid-Pacific Country Club in Kailua, Hawaii recently. Though his trip was brief, he was spotted dining at Noi Thai Cuisine with his sister and one of his other go-to favorite spots, Buzz’s Steakhouse in Kailua. He has a vacation home in Kailua, which is just over the Ko’olau Mountains toward the Windward side of Oahu. He typically likes to dine at local restaurants and play golf while he’s on island, and that’s exactly what he did this time around. This side trip to his home state was a stopover on his way to French Polynesia.
Obama knows Hawaii well, having been born in Honolulu, and throughout his presidency the 50th state offered a comfortable refuge far removed from the Washington scrum. Here, Obama enjoys a traditional “shave ice” from the popular Island Snow at Kailua Beach Center in Kailua, Hawaii.
In January, the Obamas retreated to the Palm Springs home of Michael S. Smith, who redecorated the White House when the Obamas lived there, and James Costos, ambassador to Spain and Angora during Obama’s presidency. The 11,000-square-foot home, designed by architect Howard Lapham, overlooks Sunnylands, which was once owned by Walter and Leonore Annenberg and played host to many past presidents. The kept a relatively low profile during their trip to Palm Springs, but we’re guessing Obama played a few rounds of golf while he was there (hopefully with his hat backwards). You can’t rent out this specific Thunderbird Heights home, but you can find other sprawling estates for rent nearby on Airbnb.
According to the latest reports, Barack and Michelle Obama, along with close personal friends like Bruce Springsteen, Oprah, and Tom Hanks, are all hanging out together and sailing around French Polynesia on the yacht of billionaire entrepreneur Larry Ellison.
In early April, they all met up and ventured to Vanilla Island for lunch, making their way to Taha’a (pictured here) later in the day.
And if they stick to their current trajectory, they’ll make landfall in Bora Bora before returning to The Brando, where the former president will likely resume work on his memoirs while staying as far away from the White House as possible.
Supermodel Natalia Vodianova has a girl crush on Julia Roberts in Pretty Woman: