The Coolest Vintage Photos of Celebrities on Vacation
For your warm-weather mood board.
Obviously, celebrities have always taken luxurious vacations. But pre-social media, celebrity vacation imagery was very different—not a curated shot, or a far-off paparazzi picture, but a low-key, "normal" photograph that wouldn't look out of place in a family photo album. (You know, if your family were celebrities.)
Vacation style also used to be more formal than it is today. So when we look back at photos of celebrities on vacation, we see chic style, glamorous backdrops, and unexpectedly wholesome moments. So we rounded up the coolest examples.
Paul Newman and Joanne Woodward
Here, Paul Newman is on location filming the movie Exodus; he and wife Joanne Woodward pose for a picture while sightseeing in Jerusalem. This is 1959—the couple had married one year prior and would welcome their first daughter this same year. Their matching polo shirts are incredibly chic!
Cary Grant
I'll just leave the original 1938 caption here: "Returning from a vacation in Europe, Cary Grant, strong, silent man of the movies, takes pot shots with his camera at the New York skyline, as he comes up the bay on the S.S. Ile de France. Also on board the ship is Phyllis Brooks, whom Grant is to marry in the near future." His signature suit is as dapper as ever.
Deborah Kerr
Now this is a view. British actress Deborah Kerr is on holiday in the mountains (potentially Switzerland) circa 1966. Frankly, her all-white tonal outfit, with polished button-down and capris, is the platonic ideal of a vacation outfit. Bonus points for that chic chignon.
Ryan O'Neal
Here, Love Story actor Ryan O'Neal and his then-wife, American actress Leigh Taylor-Young, are on holiday in London with their son, Patrick O'Neal. Leigh in particular looks so glamorous in her black trousers, double belt, and scarf tied around the shoulders.
Joan Caufield
As the original 1954 caption notes, "Actress Joan Caufield and her husband, producer Frank Ross, leave for a 13-week vacation abroad Wednesday and they expect to do a lot of sight-seeing. That's why Joan is taking along a dozen pairs of extra shoes." That is...a relatable problem, I'm going to be honest.
Shelley Winters
Could someone look any more apres-ski? Shelley Winters chills out (literally) in Sun Valley, Idaho, circa 1949. The pretty red sweater with contrasting stripes at the arm is already a weather-appropriate look, but the matching lip is even better.
Roger Moore and Dorothy Squires
Look how young Roger Moore looks here! This is his second wife, Welsh singer Dorothy Squires, and they're arriving on vacation at London Airport in 1957. Squires is an absolute delight here; her white shades and skirt suit are so luxe, and I love the stuffed panda.
Janet Leigh and Tony Curtis
Janet Leigh and Tony Curtis, who were married at the time, are aboard the "Lurline" cruise ship and headed to Honolulu, Hawaii. The Psycho actor is a vision in a canary-yellow one-piece; she and Curtis were married from 1951 to 1962, and this is circa early 1950s.
Ingrid Bergman
Per the 1952 caption, "Swedish actress Ingrid Bergman giving her son, Robin, a piggyback while on holiday in Portofino in the Tigullio Gulf, Liguria, Italy." Bergman, in shorts and a striped collared tank, somehow manages to look relaxed and put-together.
Raquel Torres
Quoth the 1933 caption: "Raquel Torres...dons silks and rides a mount just to see how it feels to be a jockey, during a vacation at Agua Caliente, popular Mexican racing and gambling resort." Torres makes equestrian-wear look extremely chic, thanks to those knee-high boots.
Carmen Miranda
Portuguese-born Brazilian actor and singer Carmen Miranda arrives at Grand Central for a vacation in New York. Insert joke about how she's not wearing her signature fruit hat, which was a huge part of her on-screen persona. But I love that head wrap and enormous coat!
Anjelica Huston And Assaf Dayan
Anjelica Huston And Assaf Dayan relax in the Piazza Navona in Rome. The two are there to film A Walk With Love and Death (filmed by Huston's father John); this is probably a picture of them between filming scenes. That pleated mini and patterned tights are stunning.
Kim Novak
Vertigo actor Kim Novak sits at Piccadilly Circus during a televised sightseeing tour of London. Despite the very obvious staging (including curious onlookers), she looks highly relaxed. That polka-dotted dress is gorgeous and architectural, and the pumps are pretty—if a bit unrealistic for long bouts of walking.
Joan Crawford
We normally know Joan Crawford in the context of her intense film roles. So this photo feels particularly joyful. She might also look so content and blissful because, as the caption notes, "The 47-year-old actress recently wed American industrialist Alfred Steele and they are honeymooning in this famous island resort [at Capri]."
Katharine Hepburn
May we all look so effortlessly chic getting off a plane as Katharine Hepburn. She's on a trip to New York; "Carrying heaps in her arm, she hurries from Newark Airport after arriving on the TWA air liner Sky Chief." I love a long coat, and this one's perfection.
The Kennedys
On vacation in Gstaad, Switzerland, Jackie, Caroline, and John Kennedy look like they're having a blast sledding. (This was in 1966, a few years after the passing of JFK). It's very difficult to look luxurious in a warm puffer jacket, but Jackie's doing it with ease.
John Wayne and Sophia Loren
I honestly just love this photo and need to know more: John Wayne and Sophia Loren go sightseeing in Rome in between filming Legend of the Lost. Together, they climb over a gate while Loren speaks animatedly. I need to know more about that coat and patterned jumper.
Jerry Hall
Model Jerry Hall is photographed with her daughter, Elizabeth Jagger, while the two vacation on Mustique circa 1991. The two are both enjoying a snack and clad in gorgeous summer dresses. Honestly, it feels quite perfect for a casual island vacation.
Debbie Reynolds and Eddie Fisher
Debbie Reynolds and Eddie Fisher vacation over the July 4, 1954, holiday in Las Vegas, Nevada. This is before the two were wed in 1955; if you're unfamiliar, the union ended abruptly when Fisher left Reynolds for Elizabeth Taylor (Reynold's best friend). I will say: I love that gorgeous patterned swimsuit.
Lucille Ball
What I love about this photo is how relaxed Lucille Ball looks. For a performer who relied so heavily on energy and verve, it feels surprising to see her chill while on vacation at the Roney Plaza Cabana Club. Also, that vest and trouser combo is top-notch.
Grace Kelly
The erstwhile Grace Kelly, now Princess of Monaco, sits with her children Albert and Caroline on a snowy sled in 1962. They're in Gstaad, Switzerland, and everything about Grace's outfit is perfect: the cable-knit sweater, the fuzzy hat, the cigarette-style pants, and (of course) those warm slipper boots.
Ingrid Bergman and Roberto Rossellini
This basically looks like a photo from a movie, and no wonder. The original caption notes, a bit cheekily, "From a balcony of the Grand Hotel, Ingrid Bergman, movie star, and Roberto Rossellini, Italian director who she wed after divorcing Dr. Peter Lindstrom, look at the world go by—that part of the world that travels on the Grand Canal of Venice—during their recent visit to the resort."
Jackie Kennedy
Jackie Kennedy, who was by this point married to Greek business magnate Aristotle Onassis, walks up the steps to the Acropolis in Athens. She was apparently joined by Greek friends on the sightseeing tour. Jackie's vacation style was always second to none, and this shift dress and sandals work perfectly with those sunglasses.
Elizabeth Taylor and Richard Burton
There was always a ton of media scrutiny on Elizabeth Taylor and Richard Burton—especially since they started their affair while married to other people. Here, the two are on holiday in Israel in 1975. They'd divorced in 1974 and remarried this year, and the public was fascinated. She's so colorful in yellow!
Raquel Welch
Actor-singer Raquel Welch is visiting the Colosseum in Rome here. This is 1966, the same year that One Million Years B.C. was released—making Welch an international star. I love that signature beehive, the simple spaghetti-strap dress, and those gorgeous kitten heels.
Rita Hayworth
Here, Rita Hayworth vacations at Megeve in the French Alps with her two daughters. Hayworth was a fan of headwear, and this white scarf is extremely chic (and thematic in the snow!). The rest of the outfit is simple and tonal, and those gloves look quite warm.
Princess Diana
Princess Diana had enviable vacation style. Here, she plays on the beach with Princes William and Harry; this is Necker Island in the British Virgin Islands, owned by Richard Branson. The leopard print bathing suit and matching sarong are pitch perfect for a casual but upscale beach trip.
Faye Dunaway
Celebrities always have better airport style than the rest of us. See also: Faye Dunaway headed to London on vacation. The fur-lined jacket, boots, and hat lend a nice cohesion to the whole look. I love that her gorgeous waves make her look literally windswept.
The Beatles
Beatles riding donkeys! They're on a beach in Weston-super-Mare before a concert in 1963. This is a perfect example of what I mean when I say vacation style used to be quite formal. They're all wearing button-down shirts and, in John and George's case, full jackets.
Audrey Hepburn
Audrey Hepburn's posing for photos on a golf course at the Bürgenstock resort, Switzerland, in 1954. (Some of the photos show off her golfing skills and posing with then-husband Mel Ferrer). The two were married in Switzerland that same year, and these photos may be for a profile of their relationship. That simple white frock is stunning.
Brigitte Bardot
Per the 1956 caption, "Brigitte Bardot takes time out from relaxation at the famed resort of Cortina to pose for photographers." This was right around the time she starred in And God Created Woman, launching her to superstardom. There's some really awesome layering at play here, including the thin shirt under her sweater.
Elizabeth Taylor and Richard Burton
So much of the coverage around Richard Burton and Elizabeth Taylor was focused on the drama of their relationship. So I love this family-centric picture while they vacation on the French Riviera in 1965. Also, I love Taylor's chunky jewelry and sunny top.
