The Best-Dressed Moments From Old Hollywood’s Awards Show Heyday

Between the polished studio stars, the juicy lore, and that magical movie lighting that made pores disappear and eyes sparkle, it’s easy to get swept up in the dreaminess of Old Hollywood. Plus, how cool is it that the storied awards shows that punctuate each season of TV and film today were still in their nascency, most having been started between the ’20s and the ’40s? Like today, the screen sirens back then walked the red carpet decked out in the most glamorous fashions, befitting the stars of new media. 

We can’t stop thinking about Elizabeth Taylor’s corseted gown and darling little pixie haircut, Joan Collins’ bubble skirt, or the ‘fit Grace Kelly wore for one of her last Hollywood appearances before she picked up the title of Princess of Monaco. In short, the leading ladies who made our list had some truly iconic awards show moments, and we’ve got the pics to prove it.

Singer and actor Doris Day would win four Golden Globes over her career, but she picked up the first one of those at the 15th annual ceremony in Hollywood in 1958. The “Pillow Talk” lead won the World Film Favorites honor, and she accepted her award, presented by Gene Kelly, dressed in a full circle skirt made voluminous with layers of cloud-like tulle. The star paired that with a cropped double-breasted white jacket, and — for an added touch of ooh-worthy dark glamour — long black opera gloves. 

The British Academy Film Awards — also known as the BAFTAs — was only on its third annual go-round when British actor Honor Blackman attended the ceremony, in London in May 1950. The star was a Bond girl in 1964’s “Goldfinger,” and she even made a brief cameo in “Bridget Jones’s Diary.” On this night, Blackman foreshadowed the funkiness of the ’80s a bit, donning a black gown with a nipped waist, jewels along the bodice, and featuring petal-like folds. She accented the dress with white mesh fingerless gloves and a sculptural necklace.

Elizabeth Taylor was a regular during award show season, walking the red carpet and, we imagine, flitting around in the banquet halls. Taylor attended the 25th annual Academy Awards in Hollywood in March 1953 with her then-husband Michael Wilding. The star chose a corseted gown that was anything but quiet luxury, adorned in embroidery, jewels, and layers of tulle at the bust and down the skirt. Her trademark brunette hair was the perfect complement. 

The 30th annual Academy Awards took place in March 1958, and British-born actor Joan Collins attended wrapped in a strapless dress with a fitted bodice, pointed bust, and a full bubble skirt with an asymmetrical hem. The long white gloves that stretched nearly the length of her arms added an extra punch of romance. Best known for her role in ’80s soap opera juggernaut “Dynasty,” Joan Collins’ Cannes look at 92 proved stealing the show isn’t just for the young. 

The 28th annual Academy Awards were held in Hollywood in March 1956, and Grace Kelly was a much buzzed-about attendee, draped in a white ball gown decorated with flowers and cape shawl that delivered, aptly, both bridal and royal vibes. The following month, the model-turned-actor would marry Prince Rainier of Monaco, taking on the title of Grace Kelly, Princess of Monaco. With this move, she effectively retired and left Hollywood to be a full-time noble, wife, and mother. 

Dinah Shore was invited to the 10th annual Primetime Emmy Awards in Los Angeles in April 1958. For the ceremony, she opted for a gown in a simple silhouette made special with swirls of sequins and stones that reminds us of a work of modern art. It’s so delightfully whimsical and fitting for a performer who, that night, accepted an award for her long-running variety show, “The Dinah Shore Chevy Show.” The gloves added an incredible detail that, even now, inspires the fans to discover more ways to embrace the dramatic opera glove trend.

Hattie McDaniel won Best Supporting Actress at the 12th Academy Awards held at the Ambassador Hotel in Los Angeles in February 1940, making her the first Black actor to win an Academy Award. McDaniel, who won for “Gone with the Wind,” was invited to the ceremony only after producer David Selznick challenged the venue’s “no Blacks allowed” policy. Still, she wasn’t allowed to mingle with her white co-stars but was instead forced to sit at a small back table. This photo was snapped later in 1945, showing McDaniel holding her historic award draped in a luxe sequin-covered shrug that sparkled and shone.

A regular on the red carpet during awards show season, this throwback pic of Grace Kelly from the 1955 Oscars highlights one of her most chic looks ever. What the star wore to the 27th annual Academy Awards oozed quiet glamour and sophistication, with the delicate double spaghetti straps, the soft pistachio color, and the subtle draping. We especially love her pulled-back hair, coral lip color, and barely-there jewelry. Kelly won the Best Actress trophy on this night for her role in “The Country Girl.”

Victoria Shaw was one of the stars in attendance for the 13th annual Golden Globe Awards in Los Angeles in February 1956. On this night, Shaw took the stage to accept the Most Promising Newcomer award for her role in “The Eddy Duchin Story,” dressed in an ultra chic look that felt expensive yet playful. Shaw wore a strapless gown in a metallic-like fabric covered in polka dots and satiny pointy pumps. 

Equal parts charming and cheeky, multi-hyphenate Carmen Miranda popped out for the 13th annual Academy Awards in February 1941. “The Brazilian bombshell” —  born in Portugal but raised near Rio de Janeiro — wore a long gown with intricate beading and embroidery, and cutouts on the sides (a sexy move for the time, no doubt.) She paired the dress with a funky yet glamorous white fur coat and a striped headpiece, a version of the accessory that will always be associated with the performer and that perfectly captured her playful spirit.