Old Hollywood Dresses That Are Still Setting The Fashion Trends Today

The concept of Old Hollywood encompasses the golden age of film alongside the glamour cultivated by Jazz Age icons and silver-screen stars. Roughly ranging from the 1920s to the 1960s, this era of cinema explored major technological advancements in filmmaking while helping evolve the idea of "celebrity" to what we know it as today. Naturally, just as classic films continue to influence contemporary filmmaking, the Old Hollywood aesthetic is still informing red carpet trends today. 

In truth, Old Hollywood glamour isn't just one precise style. Not only did makeup and hair techniques shift with the evolution of technology, but the aesthetic manifested differently for different stars. For instance, Audrey Hepburn embodied a sense of effortless elegance in tailored pieces and classic accessories, while Marilyn Monroe pushed boundaries as a glittering bombshell. While distinct in their personal style, both women are considered icons of Old Hollywood glamour today. 

Even so, there are certain elements and vibes associated with the label. For one, Old Hollywood glamour balances sophistication and luxury with accents like jewels, evening gloves, and voluminous curls. In terms of dresses, expect silky fabrics, body-skimming silhouettes, and strapless necklines. With all this in mind, it's clear which Old Hollywood dresses inspired contemporary stars today, and some of these tributes are downright iconic.

One of Audrey Hepburn's most recognizable looks originates from "Breakfast at Tiffany's." In the 1961 film, she wears a black sheath dress designed by Givenchy and costume designer Edith Head, accessorizing with elbow-length gloves, a small tiara in her updo, and a five-strand pearl necklace featuring a glittering diamond at the throat. The polished glamour of this unmistakable Hepburn ensemble has been referenced and recreated endlessly in subsequent decades, with Anya Taylor-Joy among many celebs to bring the look into the modern era.

The blond beauty fittingly stepped out at a Tiffany and Co. launch event wearing a black, trumpet-shaped gown with beading along the neckline and down the skirt. She styled the vintage Dior piece with a sophisticated updo, a ruffled jacket worn at her elbows, and an assortment of white-yellow jewelry from the launch.

Audrey Hepburn's influence goes beyond "Breakfast at Tiffany's," with the glittering ball gown she wore in "My Fair Lady" being another of her many iconic looks. The ivory-colored evening dress, designed by Cecil Beaton, combined a '60s-style sheath silhouette topped by gossamer tulle with ornate embroidery inspired by 1910s fashion. Hepburn also wore a showstopping choker that extended to her collarbone and a voluminous bouffant topped with a tiara.

While the regal look has been reinterpreted across various runways, Kendall Jenner modernized the ball gown for the 2021 Met Gala. Designed by Givenchy, the piece emulated the intricate embroidery seen in the film, but used sheer fabric to create the popular "naked dress" appearance over a subtle, nude-tone corset. Jenner completed her Old Hollywood ensemble with a thick, sparkling choker and a more pared-back updo. Clearly, modern interpretations of Hepburn's refined style can take many forms.

Marilyn Monroe continues to be one of the most enduring figures of Old Hollywood. The hot pink dress she wears during her performance of "Diamonds are a Girl's Best Friend" in the film "Gentlemen Prefer Blondes" ranks among the most iconic. Not only does the strapless, bow-adorned look land among Monroe ensembles filled with hidden meaning, but it also provided endless fashion inspiration for subsequent decades.

For instance, "Where is My Husband!" singer Raye stepped out at the 2021 Brits Awards in a custom, bright pink gown from Etro that featured sequins along the neckline, pink gloves, and a thigh-high slit in the skirt. "I am so obsessed with the Fifties and Sixties," she told Harper's Bazaar. "I think that style of dressing is just so flattering on a curvy woman — it's all about just embracing our hips and boobs and I just love it."

The sheer gown that Marilyn Monroe wore to sing "Happy Birthday" to President John F. Kennedy in 1962 continues to set trends today. Designed by Bob Mackie and created by Jean Louis, the figure-hugging piece created the illusion that sparkling crystals were dotted directly onto the skin, and was styled with the star's signature bob and a pair of chandelier earrings. Despite using a popular silhouette of the era, the gown epitomized Monroe's ability to push the boundaries of acceptable fashion.

Doja Cat put an edgy spin on the look when she attended the Grammy Awards in 2022, wearing a sheer, crystal-adorned gown over a baby blue corset. The "Say So" singer styled the Versace pieces with platform heels and a spiky, bleached-blond hairstyle. The resulting look takes clear inspiration from Monroe, but with a modern, alternative twist, pointing to Old Hollywood's enduring influence.

Josephine Baker's status as a Jazz Age icon includes her dazzling and theatrical wardrobe. While touring America in the '50s, she took the stage in a memorable evening gown that exuded Old Hollywood glam. The custom Dior piece consisted of a strapless neckline and a fitted silhouette, featuring beaded embellishments that tapered off toward the hemline. The bombshell completed the ensemble with a large fur coat, intricate hair pieces, and opera gloves.

Yara Shahidi honored Baker when attending the 2021 Met Gala, working with Dior to create a gown inspired by the cultural icon's onstage look. The "Grown-ish" actor wore a taupe-toned gown adorned with silver and white embroidery and fitted with a train and veil made of gold tulle. "My goal was to pay homage to [a] powerhouse renegade black American artist," she told Vogue. "I just hope I was able to do that."

While Shirley MacLaine might be better known for classic films like "The Apartment" and "The Trouble With Harry," her starring role in "What a Way to Go!" was paired with several showstopping, Edith Head-designed looks that are truly unforgettable. When Sabrina Carpenter walked the red carpet at the 2025 Grammys, she definitely had MacLaine's backless dress, blond wig, and cigarette holder on her mind. 

The "Espresso" singer wore a powder blue dress by JW Anderson with a chain of teardrop diamonds hanging down her back, ending with a glittering round jewel suspended just above her coccyx. Carpenter made the dress her own with feather embellishments around the waist, styling the piece with a curly updo that completed the Old Hollywood vibes.

Joyce Bryant is another Old Hollywood icon who continues to inspire modern trends. The jazz singer rose to fame in the '40s and '50s, with her figure-hugging stage wardrobe created by influential costume designer Zelda Wynn Valdes. The California native was pictured on the cover of her album "Runnin' Wild" in one of Valdes' deep-cut creations, with the gown's sweetheart neckline and ruched bodice pictured in black and white against the cover's bright orange background.

Zendaya paid homage to Bryant alongside other Black icons at the Golden Globes in 2025. Styled by her long-time collaborator Law Roach, the actor stunned in a satin dress from Louis Vuitton that paired a figure-hugging silhouette with a dramatic train. While the orange hue and strapless neckline feel like direct inspiration, Zendaya completed her vintage glamour with a curled bob more reminiscent of cited reference Dorothy Dandridge.

Grace Kelly is another memorable Old Hollywood icon, and the "Rear Window" star's wardrobe was defined by traditional femininity and timeless elegance. The dress she wore to the 1955 Academy Awards, where she accepted the award for Best Actress for her role in "The Country Girl," is a great example of her classic style. The Edith Head design was made of a stunning silk, featuring double spaghetti straps and draping across the hips.

Elle Fanning embodied this classic glamour when virtually attending the Golden Globes in 2021. She was pictured in a silky mint green Gucci gown adorned with rhinestone straps and a sweeping train, completing the look with silver heels and a sleek bun. "I have always loved the classic glamour of women like Grace Kelly and wanted to pay homage to them," she told Vogue.

Rita Hayworth cultivated a femme fatale reputation, and her role in the 1946 film "Gilda" was a prime example of this bombshell persona. The silky black dress she wears in the classic movie ranks as one of her most frequently referenced. Crafted by Columbia Pictures designer Jean Louis, the sheath gown consisted of a strapless neckline and asymmetrical draping gathered at one hip. The piece was styled with her signature loose curls and a pair of matching evening gloves.

Nicole Kidman added to the list of celebrity revenge dress moments we could never forget by taking inspiration from the Old Hollywood icon. After filing for divorce from Keith Urban in October 2025, the Aussie walked the runway for Vogue World: Hollywood in a Chanel gown featuring additional ruching at one shoulder and a leg-baring slit. Clearly, Kidman can do bombshell just as well as her classic inspiration.