Marilyn Monroe's Best Fashion Moments of All Time – PEOPLE

Fashion

Contributor, PEOPLE
Both on screen and in public, Marilyn Monroe was as glamorous as could be, swathed in luxurious gowns that would go down in history as some of the most iconic of all time.
She often wore elegant looks created by costume designers like William Travilla in her films — and would pull some of the gowns for red carpet premieres, too. Photographer Milton Green’s wife, Amy Greene, relayed to Elizabeth Winder for her book Marilyn In Manhattan: Her Year Of Joy, “Whenever she needed something to go out, she’d go to her friend in the wardrobe department at Twentieth. She’d borrow something, and then the next morning she’d bring it back with a $50 bill slipped in.”
As for her most memorable fashion moments, there are few who aren't familiar with the plunging white halter gown with a pleated skirt she wore in The Seven Year Itch or the floor-length hot pink gown with an oversized bow that she titillated audiences with while performing "Diamonds Are a Girl's Best Friend" in Gentlemen Prefer Blondes.
The beige beaded gown that she wore to sing “Happy Birthday” to President John F. Kennedy in 1962 is equally as famous. Kim Kardashian wore the dress to the 2022 Met Gala. While Dr. Justine De Young of the Fashion Institute of Technology told PEOPLE the move was “irresponsible and unnecessary,” Monroe’s estate supported Kardashian, with Nick Woodhouse of Authentic Brand Groups (the company in charge of the estate) saying that Monroe would’ve celebrated the reality star’s choice of wardrobe.
Keep reading to revisit all of the other incredible fashion moments Marilyn Monroe created over the years.
For her wedding to neighbor James Dougherty, Monroe, then 16 and known as Norma Jeane Mortenson, chose a simple streamlined gown with ruched sleeves and a modest scoop neckline. The couple, who were wed for four years, married at the suggestion of Monroe’s foster mother to avoid sending her back to the orphanage, according to Dougherty. As he later told United Press International in 1990, per the Los Angeles Times, “I never knew Marilyn Monroe, and I don’t claim to have any insights to her to this day. I knew and loved Norma Jeane.”
For a portrait session in January 1946, Monroe wore a simple red crewneck sweater, a pair of houndstooth Bermuda shorts and a brown Western belt.
During another photo shoot in 1946, the future actress looked like a young Judy Garland in overalls and a red striped top with her hair in a red bow.
The actress wore this show-stopping number, which featured a tight bodice with an off-the-shoulder neckline and a tiered skirt embellished with bows, early on in her film career.
Shortly after being signed by 20th Century-Fox, the 21-year-old showed off a far more demure style than the one she would come to be known for during a 1947 photoshoot with Earl Thiesen. She stood in the grass in a floor-length robin's egg blue frock with floral embroidering at the bust, sleeves and skirt. The dress also featured see-through sleeves.
The same year she made her film debut, the starlet looked radiant while visiting talent agent Johnny Hyde in a pair of shorts that showed off her legs and a quarter-sleeve turtleneck with banded stripes at the arms and collar.
Monroe breathed new life into the little black dress with this off-the-shoulder version she wore in the 1950 film The Asphalt Jungle. She paired the number with black sheer tights and black heels.
The Hollywood legend was pictured in many different bikinis throughout her career, but this polka dot one circa 1951 is perhaps the most known. The suit featured ruffled trim for added flirtiness.
For her one and only appearance at the Oscars, where she presented the Academy Award for Best Sound Mixing, Monroe chose an ultra-glamorous, black off-the-shoulder princess dress. The gown was reportedly created for Italian actress Valentina Cortese for the 1951 film The House on Telegraph Hill.
The actress looked glamorous while wearing a lacy black robe over a pink gown to read fan mail shortly after the release of her latest picture, The Asphalt Jungle.
Dressed down in a black turtleneck and a pair of white capris, Monroe looked sharp and elegant for a series of photographs taken for Life magazine by photographer Alfred Eisenstaedt. Her outfit was later recreated by Ana de Armas for Netflix’s Blonde biopic.
For her part as Rose Loomis in Niagara, Monroe wore a cropped suit jacket and a matching pencil skirt with a strapless blue top with a bow at the side.
One of Monroe's most iconic looks is the hot pink strapless number she wore for her "Diamonds Are a Girl's Best Friend" number in Gentlemen Prefer Blondes.
“I took a brilliant candy-pink silk peau d’ange made in Paris and flattened that to a giant billiard felt with an overlay of silk,” designer William Travilla said in 2011’s Dressing Marilyn, per Vogue. “Apart from the two side seams, the dress was folded into shape rather like cardboard. Any other girl would have looked like she was wearing cardboard, but on screen I swear you would have thought Marilyn had on a pale, thin piece of silk. Her body was so fabulous it still came through,” he explained.
Travilla accessorized the famous dress with a pair of matching opera-length gloves. As for the oversized bow at the back, it was stuffed with horse hair to help it maintain its shape.
Travilla was also behind the sexy gold lamé getup Monroe was briefly spotted in during Gentlemen Prefer Blondes. The halter-style design featured a plunging neckline and sunburst pleating with an open back. It was also skintight, with Monroe reportedly needing to be sewn into it.
The actress later wore it to the Photoplay Gold Medal awards dinner, where she took home the award for most popular female star.
Though the pink dress from Gentlemen Prefer Blondes is the one most-oft referenced, the orange fishtail gown Travilla created for the film is also memorable. With ruching down the front and a beaded center, the dress is said to have caused theater-goers to gasp when the actress appeared in it alongside costar Jane Russell, who looked equally radiant in her own beaded black sequin gown.
The matching wedding dresses that Monroe and Russell wore in Gentlemen Prefer Blondes were far more dramatic than any of the dresses the blonde bombshell wore for her real-life nuptials to Dougherty, Joe DiMaggio and Arthur Miller. Designed by Travilla, they featured a mock neck, a sheer lace bodice with voluminous bell sleeves and a pleated tulle skirt. They also buttoned halfway up the back.
Monroe and her Gentleman Prefer Blondes costar Russell looked gorgeous in near-matching halter dresses while having their hand and footprints immortalized in wet cement at the Grauman's Chinese Theatre. Though both gowns were cut to the mid-calf, Monroe's featured eyelet detailing throughout while Russell's had a polka dot print.
"Marilyn and I were invited to add our footprints to those already cemented in at Grauman's Chinese Theatre on Hollywood Boulevard. We were both wearing summer dresses and high heels as we posed, arms linked together, for the photographers. We were thrilled beyond words," Russell later remembered of the moment in her eponymous autobiography.
Even the swimwear for How to Marry a Millionaire, which was designed by Travilla under Charles LaMeire, looked couture. This red one-piece featured diamond pins at the hip and chest.
For the premiere of How to Marry a Millionaire, Monroe once again turned to Travilla for her wardrobe. The resulting look reportedly took six hours of prep, as she had to be sewn into the dress. It featured a sheer nude underlay and white French lace by Sophie Hallette, which Travilla personalized with sequins. It was topped it off with a white fur stole and Monroe’s signature opera gloves.
Monroe went against the traditional grain for her wedding to second husband DiMaggio, selecting a dark-colored button-down suit with a furry Peter Pan collar for their city hall ceremony.
While Monroe posed for more than 50 photos for photographer Milton Greene, the most famous was undoubtedly the 1954 Ballerina Sitting series he did with the actress — one shot of which was named as one of the top three photographs of the century by TIME magazine. Its success was due in large part due to the stunning white tulle-and-satin frock Monroe wore by New York designer Herbert Kasper. Though the dress didn’t quite fit (it was two sizes too small), requiring her to hold up the front of the bodice, she reportedly took it “in stride.”
1954's There's No Business Like Show Business saw Monroe team up with Travilla once more to bring his flashy garments to life. Here, she's seen in a form-fitting gown with beaded embellishments that crescendo into a dramatic pouf at the bottom of the skirt.
Monroe revisited a similar silhouette to the belted strapless one she donned in Gentlemen Prefer Blondes while attending the 1954 premiere of There's No Business Like Show Business, albeit with an added fur stole and a more streamlined fit.
The former model looked chic even when dressed down, as evidenced by the black-and-white striped turtleneck she was photographed in at her Palm Springs, California, home garden.
For her turn as a bar singer in River of No Return, Monroe performed in a red number with swirly black sequine embroidery and delicate beaded off-the-shoulder straps.
In 1954, Monroe performed for U.S. troops stationed in Korea in a sparkly purple spaghetti strap design. The dress was recently put on display in Bendigo, Australia, in 2016.
Everyone remembers the moment when Monroe's dress blew up over the subway grate in The Seven Year Itch. The plunging halter piece became a huge part of the actress's legacy.
Monroe reportedly wore two pairs of undergarments in order to keep the crowd from getting an eyeful while filming the scene, which took place in New York at 1 a.m. Fellow actress Debbie Reynolds later purchased the gown for $200 and sold it for over $4 million in 2011.
Another costume from The Seven Year Itch, the "tiger gown" featured black stripes over gold fabric, a slit and a tulle train. The actress also paired the look with black evening gloves.
Monroe was all smiles in 1955 when she posed for a picture in a black evening gown with a unique, yarn-like shoulder strap at one side, a strapless bustline and a mermaid tail. She previously wore the piece to the 1952 Hollywood Foreign Press Association award ceremony.
Monroe looked every bit the movie star while lounging on a white satin sheet and a white fur coat in a red brocade evening gown with spaghetti straps. She accessorized with long, dangling diamond earrings, black tights and pumps.
Smiling in a belted trench coat, Monroe looked chic and at ease outside her Brentwood, California, home.
The screen siren broke royal protocol with the gold lamé gown she wore to meet Queen Elizabeth II at a 1956 screening for The Battle of River Plate at the Empire Theatre in London. Guests were asked to dress “conservatively” and “in a suitable manner to meet royalty,” according to the 2022 book When Marilyn Met the Queen. However, Monroe’s dress, though initially covered by a matching cape, was cut low enough to show the top of her décolletage, directly ignoring the ask not to wear anything “so low-cut that they showed too much cleavage.”
The ensemble reportedly earned the Hollywood A-lister a "brief look up and down" by the Queen, who is said to have later told a friend, "I thought Miss Monroe was a very sweet person. But I felt sorry for her, because she was so nervous that she had licked all of her lipstick off."
The sleek black satin slip dress, which Monroe was photographed in while hosting a press party in 1956 is right in line with the makeover she reportedly received from photographer Greene's wife, Amy, several years prior.
An excerpt from Elizabeth Winder’s book, Marilyn in Manhattan: Her Year of Joy, revealed that Milton was “exasperated” with the star’s off-screen clothing sense, reportedly telling her, “Look. … You have something that looks fantastic on screen, but you walk around like a slob.” As Winder explained in the book, “[Marilyn would] just go back to the old clothes she was used to — slacks cut too short that never really fit, blouses that never really had the right lines.”
As the story goes, Milton even enlisted Amy to help Monroe with her closet needs. "She went to her good friend, the designer Anne Klein, and said, 'Listen, I have a friend and she's an actress' — I never told Annie who it was — 'and I need some clothes because she has no fashion sense and I have to dress her up,' Amy recalled. "And Annie said, 'Come and get what you want. The result was a capsule collection of black sheaths and slips, sexy but simple and perfectly in tune with Marilyn's aesthetics."
According to the book, once she found her style groove, Monroe had cheaper versions of the couture looks made.
While Monroe wore a pencil skirt and a simple shirt for her official courthouse wedding to playwright Miller, she had a another look lined up for a secondary ceremony in the form of a Norman Norell gown with an empire waist, a ruched neckline and a tea-length skirt. She topped it off with a short-but-sweet veil.
For the premiere of The Prince and the Showgirl, the first production from Monroe's company, Marilyn Monroe Productions, the entrepreneur dazzled in a fitted satin dress with a mermaid silhouette. She paired the ensemble with full-length gloves and a satin stole.
Australian costume designer Orry-Kelly won an Oscar for his fashion designs in Monroe’s 1959 film, Some Like It Hot, in which she wore this black-and-nude cocktail dress with beaded fringe and butterfly appliqués. It has been said that the dress was so tight, the star had to be lifted on top of the piano she sang on in it.
Monroe wore yet another of her film designs to the premiere of Some Like It Hot when she stepped out in an embellished ivory crepe gown with bugle beads that swung loosely at the bottom. Fans would later see the gown in 1960's Let's Make Love, for which Dorothy Jeakins was the costume designer.
The film legend bundled up in a luxe fur coat while boarding a plane at La Guardia airport en route to Chicago for the premiere of Some Like It Hot.
In a departure from her usual ultra-tight evening gowns, costume designer Dorothy Jeakins outfitted Monroe in a chunky cable-knit Aran sweater from Cleo Ltd and a pair of sheer black tights.
The Golden Globe winner’s ensemble for The Misfits may have been simple — she wore a brown belt, a white cotton voile blouse and a pair of Lady Levi’s (the first line of jeans for women) — but the costume had a major style impact. According to Vogue U.K., it was this very getup that helped popularize denim for women.
It wasn’t the first time she’d donned the look, either: Monroe also wore Foremost JCP jeans for 1954’s River of No Return, which were auctioned off by Tommy Hilfiger in 2017. The designer also reportedly gifted jeans previously worn by Monroe to both Britney Spears and Naomi Campbell.
Monroe threw it back to a popular '30s style with the houndstooth-printed coat she wore over a solid dress while touching down by way of jet in New York City.
Monroe took home her third Golden Globe Award in 1962. For the occasion, she donned a green sequined gown with a draped neckline designed by Norman Norell. She finished the look with a pair of sparkly diamond earrings.
Everything had to be skintight,” Norell reportedly said of designing for the starlet in the 2017 book Marilyn in Manhattan: Her Year of Joy. “You had to reinforce every seam or everything would break.”
The gown, which went on to become one of Norell’s most famous designs, was sold at Christie’s for $96,000 and worn by Kardashian to a Met Gala after party.
“To top off my night after The Met, I had the honor of changing into Marilyn Monroe’s Norman Norell dress that she wore to the Golden Globes in 1962 — where she received the Henrietta Award For World Film Favorite,” Kardashian wrote on Instagram in May 2022. “In my quest to find the Jean Louis hand-beaded dress that I wore to the gala, I discovered @heritageauctions owned Marilyn’s iconic green sequined gown. … It will forever be one of the greatest privileges of my life to be able to channel my inner Marilyn in this way, on such a special night.”
Apart from her pleated white dress in The Seven Year Itch, Monroe is also remembered for the $12,000 sparkler she wore while singing "Happy Birthday" to President John F. Kennedy at Madison Square Garden in New York ahead of his 45th birthday on May 19, 1962.
Sketched by Bob Mackie at the age of 23 and crafted by Jean Louie, the sheer beige number featured 2,500 hand-sewn crystals. The custom piece was so form-fitting that Monroe reportedly had to be sewn into it. She also forwent undergarments despite the 18-inch slit in the back.
The gown was first sold at a Christie’s auction in 1999 for a cool $1.27 million. In 2015, however, it was purchased by Ripley’s Believe It Or Not for a record-breaking $4.81 million. The figure beat the previous record of $4.6 million set by another item of Monroe’s: the pleated dress she so famously wore for The Seven Year Itch.
Kardashian borrowed the gown for the 2022 Met Gala, which had a theme of “In America: An Anthology of Fashion,” wearing it on the steps of the Met before changing into a replica. As she relayed to Vogue, “Nowadays everyone wears sheer dresses, but back then that was not the case. In a sense, it’s the original naked dress. That’s why it was so shocking.”
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