32 beautiful red carpet dresses that ooze old Hollywood glamour

Old Hollywood glamour is a timeless aesthetic and the style harks back to what many of us regard as the 'golden era' of fashion, beauty and entertainment.

Stars like Marilyn Monroe, Audrey Hepburn and Lauren Bacall are just a few of the most iconic old Hollywood icons. Rarely seen with hair out of place and always sporting perfectly winged eyeliner, these starlets dominated not just our screens but also entertainment news (and red carpets) for decades. They defined our understanding of what it means to be a film star and their influence on fashion and style trends is felt to this day. 

From Marilyn's iconic pink dress with a cinched waist to Audrey's sleek black column gown and tiara ensemble, there was nothing quite like an old Hollywood glamour dress - often characterised by their flattering cuts, impeccable tailoring and simplicity.

So, to pay homage to this amazing style era, we've put together a list of our favourite old Hollywood glamour dresses ever worn on the red carpet, from the stars of the day to modern-day takes on Hollywood glamour.

32 of the best old Hollywood dresses ever worn on the red carpet

Marilyn Monroe

A true old Hollywood icon, Marilyn Monroe was always going to have a place in this list of show-stopping dresses. In this picture, the Hollywood starlet dazzled in a gold lamé dress designed by Travilla, a dress that shimmered in the light and showcased her glamorous persona and trailblazing fashion sense that has remained influential for decades.

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Celebrity photographer Frank Trapper had a front-row seat to dozens of awards shows, premieres and events across the globe. In this collection of 1000 pictures, he takes us along the way, showcasing all the best (and most scandalous) looks of the time.

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Natalie Portman

Polka dots were a fashion staple in the era of old Hollywood, appearing on a huge range of clothing pieces, from structured blouses to skirts to headbands. Here, Natalie Portman stunned at the 2012 Academy Awards in a vintage Christian Dior gown from their spring/ summer 1954 collection. With a simple strapless design, fitted bodice and simple train, this red and black polka dot dress is a simple classic that shows old Hollywood glamour at its best on the red carpet. Portman also let her hair do the talking, with a carefully coiffed side fringe, deep side parting and sleek loose waves. 

Barbara Stanwyck

Barbara Stanwyck wore this super pretty gown at the 1941 Academy Awards, featuring delicate floral beading, scalloped neck and three-quarter length sleeves. Accessorised with a rather bling-y flower diamond necklace, flower earrings and a sparkly bangle, Barbara looked the epitome of old school Hollywood glamour (hairdo included!). 

Kim Novak

Large skirts and wide necklines are a staple of old Hollywood glamour. Here is actress Kim Novak in a dress with both of these design elements at the 1956 UK premiere of The Eddy Duchin Story in London. Its balloon-like sleeves that drape and sit beautifully appear to be made of silk while a large skirt gives movement and a touch of drama to the opulent gown. She completed the look with a curled updo - also typical of the era. 

Judy Garland

The Wizard of Oz star Judy Garland was the epitome of old Hollywood glamour in this picture. This dress is a classic old school Hollywood dress because of its luxurious fur neckline and plain figure-hugging silhouette. Paired with a classic short curled haircut, we can tell that Judy turned heads in this timeless dress.

Hattie McDaniel

Pictured accepting her Oscar for Best Supporting Role in Gone With the Wind, actress Hattie McDaniel wore this beautiful dress that incorporated plenty of florals into her look at the 1940 Academy Awards. Wearing a simple dress with a gathering just under the bust and a charming embellishment on the neckline, this dress is a wonderful old Hollywood dress that could easily be worn to this day.

Natalie Wood

Natalie Wood dazzled in this floral, sleeveless gown with a matching overcoat at the Academy Awards in 1958. With intricate detailing and shiny, eye-catching fabric, this dress didn’t need extravagant jewellery or big glamorous hair. Instead, a simple clutch bag, painted nails and simple sparkly jewellery accessorised the look, while eyeliner, arched brows and glowy skin makeup give it a feminine and elegant finish. 

Penelope Cruz

Wearing a dress that showcases its old-school Hollywood roots proudly, Penelope Cruz graced the red carpet in this vintage off-white tulle and embroidered Balmain gown from the 1950s. A strapless neckline, fitted bodice and delicate embroidered overlay give this gown an ethereal and light feel that is mirrored through to the bottom of the dress which features gathered tulle over the embroidery. Cruz embodies this era of old Hollywood too, with a sweeping fringe updo, tasteful diamond jewellery and a chic slim clutch, she looks as if she has stepped out of the Hollywood era.

Gene Tierney

Actress Gene Tierney wore this interesting dress on the red carpet at the premiere of the film The Egyptian in New York. Highlighting her classic beauty, the dress featured a floral print throughout and a rather eye-catching knotted bodice that sat just on her neckline. She finished the look off with a bold lip (naturally) and a curled bob.

Donna Reed

Donna Reed wore this timeless strapless gown with a sweetheart neckline and full skirt to the 1954 Academy Awards. A lace overlay underneath silk gives this dress plenty of drama and shape, tastefully contrasted by an asymmetrical panel starting on the left-hand side of the dress. A perfectly styled curled fringe and simple shiny jewellery makes this ensemble a classic example of old Hollywood glamour. 

Susan Hayward

Posing proudly with her Oscar, here is Actress Susan Hayward at the 1959 Academy Awards. Wearing a dress with simple spaghetti straps, a v-neckline and a tight-fitting waist, this black dress is an old Hollywood classic. With subtle flower embellishments all over the dress, this simple, tailored look shows that less can be more. Her huge '50s lashes give this look the perfect flirty finish.

Audrey Hepburn

Audrey Hepburn wore a stunning off-white Givenchy dress with a delicate floral pattern and cinched waist to the 1954 Academy Awards. She accessorised with white gloves, a simple updo and her signature cat-eye eyeliner that became synonymous with the icon’s work in films like Breakfast at Tiffany’s and Roman Holiday. This eyeliner is one of many timeless black eyeliner looks you can recreate to suit your mood and style! 

Vivien Leigh

Gone with the Wind star Vivien Leigh wore this gorgeously feminine satin gown to the 1940 Academy Awards. With a v-neckline and elaborate flower pattern, this dress epitomises old Hollywood style, owing to its floral pattern and simple design. A fresh short bob with tight curls, chunky jewellery and separated, fluttery eyelashes complete Leigh’s outfit.

Renée Zellweger

Bringing old-school Hollywood glamour into the 21st century, Renee Zellweger wore this beautiful lemon yellow vintage Jean Dessès dress from the 1950s at the 73rd Academy Awards. The gown featured a strapless bodice and long draping fabric that flowed from the bust down the middle of the dress to the floor. Her hair fits in with the theme of old Hollywood too, with sweeping curls that have been styled to one side, while the accessories add the perfect amount of sparkle to this vintage-feel outfit. 

Bette Davis

Bette Davis wore this unforgettable gown at the 1939 Academy Awards. With an iconic feathered neckline and a full bouncy skirt, this dress truly embodies the glamour of the era and its pioneering approach to design and style. Her hair is styled in sections of a tightly curled updo, ensuring the bold feathered neck remains the star of the show. The actress is pictured here with the award that she won for her performance in Jezebel.

Jane Russell

Jane Russell wore this uber-glamorous gown on the red carpet in the '50s. Highly sparkly and with a strapless neckline, Jane Russell captured the essence of old-school Hollywood glamour with a fur shawl and timeless white gloves. Elegant dangly earrings and simple makeup complete the ensemble. 

Olivia De Havilland

British-American actress Olivia de Havilland wore this gown on the red carpet at the 1947 Academy Awards. Featuring a fitted bodice, a strapless neckline and a full skirt, this dress has a gorgeous flower motif that flows from the top of the dress and down one side. Embellished with beads and sequins, this dress is a firm old-school Hollywood classic that we simply love.

Winona Ryder

Pictured here at the 2000 Academy Awards red carpet, Winona Ryder opted for a vintage dress, designed by Pauline Trigère in the 1940s, according to Vogue Arabia. Featuring a strong, structured neckline and simple column design, the actress updated the classic dress by pairing it with minimalistic makeup and a laid-back hair style.

Jayne Mansfield

American actress and '50s bombshell Jayne Mansfield was known for her sometimes risqué looks. Here she is at the 1958 Golden Globe Awards wearing a simple yet staple dress design from the old Hollywood era. With a deep neckline, thick straps and a high waist, Mansfield oozed glam in the showstopping gown. Matching gloves topped with a seriously impressive diamond bangle and heels with a bow on the front complete this beautiful old Hollywood outfit. 

Doris Day

Acting legend Doris Day was an old Hollywood icon. This wonderful picture shows the actress in a floaty, floral lace overlay dress with a matching collared coat and chic gloves. Its high-neck and simple design ensures the delicate overlay is the main focus of the look, and is tastefully accessorised with a layered pearl bracelet and pearl earrings. 

Rita Moreno

Proving that a good dress deserves to be worn again, Rita Moreno wore this gorgeous dress on the red carpet at both the 1962 and 2018 Academy Awards! The timeless dress featured a high neck on its first outing but was tailored to a more modern, strapless design for its second appearance, with a simple, fitted bodice which perfectly complemented its flared skirt with a gold flower pattern. Moreno’s hair also gives a nod to the style of days gone by, as she wears a black velvet headband. 

Jennifer Garner

Orange is not a colour often associated with old Hollywood gowns, but that doesn’t make it any less of a striking choice on the red carpet. Case in point - Jennifer Garner's vintage Valentino gown from the 70s, which she wore at the 2004 Vanity Fair Oscar Party. While it may not be from the era of old Hollywood, we think it is a pretty good nod to the golden days of film and television but with a more modern take on colour. Featuring a high one-shoulder design and a dramatic silk train, it reminds us of the sweeping yet figure-skimming style of dress from the '50s and we love it. 

Lauren Bacall

This beautiful look from Hollywood legend Lauren Bacall captures the drama and excitement of film premiers in the golden age of Hollywood. This floor-length dress with a deep neckline was beautifully accessorised with a fur shawl, kitten heel shoes and typical 1950s curls that were perfectly placed and styled, one of the many timeless hairstyles of the decade.

Reese Witherspoon

Wearing a vintage Balmain gown from the 50s to the 2006 Academy Awards, Reese Witherspoon took serious inspiration from old school Hollywood glamour and we absolutely approve! Studded with sequins and beads in a tiered style and with a wonderful slightly full skirt, this dress no doubt turned heads on the red carpet. Witherspoon’s hair is also a quiet nod to the 50s, featuring a middle parting and just a touch of texture in an up-do. Glam pendant drop earrings complete this gorgeous look. 

Loretta Young

Loretta Young wore this striking strappy gown with lots of ruffles and layering at the 1948 Academy Awards. Its interestingly placed tiers make this a rather outlandish dress compared to the typically slinky numbers characteristic of the era, but it no doubt turned plenty of heads on the red carpet. Matching gloves and a glamourous curled updo complete the look.

Marlene Dietrich

Marlene Dietrich was an icon of the golden age of Hollywood, and here she is photographed at the 1932 premiere of the film Arrowsmith. Wearing a tastefully chic velvet wrap dress with fur sleeves, she exudes old Hollywood glamour. Finger-waved hair and a side parting complete this classy look. 

Marisa Tomei

Old-school Hollywood gowns were often monochromatic and featured plenty of ruffles. Here, we can see that to be completely true as actress Marisa Tomei wears a navy blue ruffled dress by Charles James from the 1950s. Featuring a sweetheart neckline and an asymmetrical tulle ruffle skirt, this dress was deservedly brought out of storage for the 2011 Academy Awards, proving its timeless appeal. Marisa’s hair is also loosely based on the 50s red carpet style with deep-set waves and a side parting. Bright and modern jewellery gives this look a pop of colour. 

Sophia Loren

A screen icon, Sophia Loren has given us so many memorable style moments both on and off the screen. Captured here wearing a stunning gown complete with a rather dramatic floral and feathered neckline and a fitted waist that flows into a voluminous chiffon skirt, this dress captures Loren’s charm and deep understanding of style. Her iconic black eyeliner and big updo complete the look.

Elizabeth Taylor

Elizabeth Taylor wore this fun and romantic Dior gown with a full, puffy skirt and floral embellishments to the 1961 Academy Awards. Paired with her signature lavish jewellery (to be precise, ultra bling-y earrings) and memorable rounded up-do, this dress has all the best-loved design elements of old Hollywood glamour. 

Ginger Rogers

At the 1941 Academy Awards, Ginger Rogers chose a gorgeous flowing, chiffon gown with a halter neckline and delicate lace bodice underneath that was designed by actress-turned-designer Irene Gibbons. The draping peplum waist and sheer layered skirt make this dress a more future-thinking dress from the era of old school Hollywood style. Pictured here with James Stewart and Bob Hope, Rogers proudly holds her Oscar statuette. A flower headband completes this feminine ensemble. 

Ava Gardener

Ava Gardener was an icon of the screen and the red carpet. Giving us so many memorable style moments over the years (who could forget her jaw-dropping gowns from The Barefoot Contessa?!), this dress is no different. Covered in sequins and with the classic halter-neck style, the dress was paired with elegant matching gloves and a seriously impressive tiara. The look was completed with gorgeous red lipstick and sculpted cheekbones. 

Grace Kelly

At the 1955 Academy Awards, Grace Kelly proved her status as a fashion icon when she wore this  iconic ice-blue satin gown by Edith Head. Complete with a matching clutch and a classic side-part up-do, Grace epitomised sophistication in this strappy dress that showcases the true glamour of old Hollywood fashion.