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11930: Carole Lombard and Gary Cooper
Getty ImagesCarole Lombard and Gary Cooper don their best nautical attire on a sailboat in 1930. The actress paired a loose collared shirt with military-style shorts and a black hat, while Cooper wore a sailor's cap and an ascot.
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21930: Greta Garbo
John Springer Collection//Getty ImagesGreta Garbo looks out on the horizon while relaxin on the deck of a boat. The film star is dressed casually in an oversized trench coat and sailor's cap.
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31930: Clara Bow
Getty ImagesClara Bow soaks up the sun on a sailboat. The silent film star paired a pleated skirt with a buttoned up vest for her afternoon on the water.
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41932: Greta Garbo
Getty ImagesGreta Garbo is illuminated in an all-white ensemble as she sprawls across the deck of a sailboat in the mid-1930s.
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51933: Bette Davis
Bettmann//Getty ImagesAlthough Bette Davis's boat is landlocked, the star still looks like a natural, as she poses on the bow in a one-piece bathing suit.
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61935: Lupe Vélez and Johnny Weissmuller
Imagno//Getty ImagesMexican-American actress Lupe Vélez joins her husband, Tarzan actor Johnny Weissmuller, on the bow of a sailboat. The look ready for a day on the sea, with Vélez wearing a navy sailor's cap atop her curls.
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71940: Dolores del Río and Orson Welles
Earl Theisen Collection//Getty ImagesDolores del Río and Orson Welles enjoy a day on the water, making use of the stern of their ship for a photo op. The actress casually places her foot on the wheel of the ship, as Welles smokes a pipe.
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81943: Lucille Ball and Desi Arnaz
George Rinhart//Getty ImagesLucille Ball and Desi Arnaz lean over the railing of a motorboat, while sporting skipper hats and bathing suits. Ball wears an oversized white button-down as a cover-up.
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91944: Humphrey Bogart and Lauren Bacall
Getty ImagesHollywood golden couple, Lauren Bacall and Humphrey Bogart, inspect the sails on a small sailboat. At the time, the couple was just beginning their love affair after meeting that year on the set of To Have and Have Not.
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101947: Rita Hayworth
Getty ImagesRita Hayworth strikes a pose in an elegant black one-piece while sailing in 1947.
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111947: Lena Horne
Bettmann//Getty ImagesAfter headlining shows in London and Paris, singer Lena Horne sets sail on the SS America. The singer was bound for New York City dressed in a velvet skirt and overcoat.
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121947: Errol Flynn and Rita Hayworth
George Rinhart//Getty ImagesErrol Flynn and Rita Hayworth match one another in high-waisted black shorts. The actress pairs hers with a black halter bikini top and a sailing cap, as Flynn shows her a sailing knot.
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131950: Ida Lupino
Getty ImagesIda Lupino spreads out on the teak deck of a sailboat. The actress even makes a point to match her pink floral skirt to the flower in her hair.
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141951: Audrey Hepburn
Pictorial Parade//Getty ImagesAudrey Hepburn lays across the bow of a motorboat during a day on the water. The stylish actress wears a gingham print skirt, white mock turtleneck, and woven sun hat.
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151951: Vivien Leigh and Sir Laurence Olivier
Keystone-France//Getty ImagesVivien Leigh dresses to impress aboard the RMS Mauretania with her husband, Laurence Olivier. The Hollywood couple sailed on the ocean liner from London to New York in 1951.
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161953: Jacqueline Bouvier and John F. Kennedy
Getty ImagesWhile they were engaged, Jacqueline Bouvier joined John F. Kennedy on his sailboat during a visit to Cape Cod. The future First Lady wears a sleeveless button-down blouse and high-waisted shorts.
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171954: Audrey Hepburn
Getty ImagesAudrey Hepburn poses for a promotional shoot using a prop sailboat in 1954. While the boat isn't actually at sea, the actress looks the part in a plaid button-down and white high-waisted shorts.
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181955: Ava Gardner
Getty ImagesAva Gardner leans against a taut rope on the bow of a sailboat during a day on the water. The film star looks relaxed with her sleeves rolled up and feet bare.
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191955: Grace Kelly
Getty ImagesLeave it to Grace Kelly to look just as elegant on a sailboat as she does at a movie premiere. The Hollywood actress wears a crisp button-down with a pair of high-waisted patterned trousers for an event at the Cannes Film Festival.
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201955: Janet Leigh and Tony Curtis
Silver Screen Collection//Getty ImagesJanet Leigh cozies up to her husband, Tony Curtis, in the front seat of a speed boat. Whether intentional or not, the Psycho actress's red pout perfectly matches the interior of the vessel.
Jennifer Algoo is the Visuals Director at Harper's BAZAAR. She is a graduate of the School of Visual Arts and has previously worked at Patrick McMullan Co. as well as completing internships at Martha Stewart Weddings, Vogue and CosmoGirl! Magazine. Jennifer covers royal, celeb and art content as well as overseeing all visual assets on BAZAAR.com. When she's not obsessing over the royals you can find her attempting to solve cold cases as an armchair detective, traveling and experimenting with new recipes.
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