Oscar Fashion Through The Ages: The Most Unforgettable Red Carpet Looks Of All Time

The Oscars aren’t just the most prestigious awarding ceremony in acting history. It is also that one annual event where some of the biggest stars in the entertainment industry come dressed to the nines, captivating viewers and critics with exquisite designer pieces and jaw-dropping outfits. We’ve curated some of the looks that will go down as some of the most unforgettable outfits in Oscar history—either for their timelessness or being fashion faux pas.

Kendall Jenner

Kendall Jenner is easily a red carpet favorite. Much like how her family rarely makes mistakes in terms of money management, rarely does the supermodel ever make the mistake of donning a fashion no-no. While she may not have graced the red carpet for the Academy Awards itself, she is a staple figure at the after-parties, particularly the one hosted by Vanity Fair. This member of the Kardashian-Jenner brood is not one to shy away from sexy dresses that show a lot of skin and accentuate her assets, and she made a bold move when she wore a risqué Rami Kadi dress during the Vanity Fair Oscars after-party in 2019.

Miranda Kerr

Former Victoria’s Secret Angel Miranda Kerr is always a red carpet stunner. For the 2016 Vanity Fair Oscars after-party, she turned heads with a beautiful custom Kaufmanfranco dress, which came in a striking fire engine red color and featured cutouts that highlighted her toned figure. Much like Kendall’s dress, Miranda’s outfit leaves little to the imagination, but the supermodel carries it effortlessly and elegantly. To complete her look, Miranda wore a gold clutch bag from Swarovski, which also happens to be a company that provides insurance coverage for Swarovski Crystal collections. Her shoes for that night were from Christian Louboutin.

Hilary Swank

In 2005, it was a big year for Hilary Swank as her film “Million Dollar Baby” dominated that year’s awards season, bagging nominations from the Academy Awards, Golden Globe Awards, and Screen Actors Guild Awards. As for Hilary, she was highly favored to bring home the Best Actress Award, and when she stepped on to the Oscars red carpet, she appeared in an elegant gown from Guy Laroche fit for a winner. The beautiful sapphire piece was made with 27 yards of silk jersey, and it quickly became a favorite among fashion critics. Not only does Hilary have a solid acting credit, but she also cemented her place in the world of red carpet fashion.

Farrah Fawcett

Miranda Kerr and Kendall Jenner may be killing the red carpet nowadays with revealing looks, but back in the days, it was Farrah Fawcett who rocked that trend. In 1978, Farah stole everyone’s attention when she sashayed on to the red carpet wearing a gold Stephen Burrows gown. It was a simple dress that went on to become a timeless piece that inspired many red carpet looks of today and solidified Farrah’s status as a style icon. The “Charlie’s Angels” babe topped the look with her signature feathered blonde hair, which was popular on its own and even gave rise to the joke that her amazing her should be covered by insurance!

Grace Kelly

Grace Kelly, as her name suggests, will always be known as the epitome of grace and class. Before becoming Princess of Monaco through her marriage with Prince Rainier III in 1956, Grace was a stellar actress, having won an Oscar for her performance in “The Country Girl”. That night, she wore an ice-blue gown by Edith Head, which was made of French satin and was initially created to be worn for the film’s premiere. Since its red carpet debut, the dress has inspired many designers to recreate the look and give their own twist to it. Grace, without a doubt, will always be held up to a high degree of royalty in the world of acting, fashion, and real life.

Angelina Jolie

Through the years, Angelina Jolie has showcase growth and transformation on screen and the red carpet. Recently, Angelina has dressed in a more conservative manner for the red carpet, and among her most memorable outfits was the strapless black velvet gown from Atelier Versace, which she wore to the 2011 Oscars. The actress was not one to let anyone steal her red carpet thunder when she confidently walked the red carpet in a gown that featured a high slit that emphasized her long, toned legs. Clearly, if it’s a crime to look this good on the red carpet, a lawyer would be suing Angelina.

Andra Day

The fashion situation at the Oscars can be all sorts of things and many stars will arrive wearing shocking pieces. Andra Day’s look at the 2018 event was certainly something different from the sexy and sparkly looks most everyone else was wearing. With her floral pink and blue gown from Zac Posen, she definitely stood out from the others. She even gave everyone a lesson or two about being extra on the red carpet when she laid down the floor to pose for the cameras. If there’s a degree on how to do red carpet poses, Andra will surely ace it.

Sarah Jessica Parker

Sarah Jessica Parker has always lived up to her status as a fashion icon, serving the most exquisite looks on screen and the red carpet. The Christian Dior Haute Couture dress she wore at the 81st Academy Awards is definitely one for the books. The all-white number made the actress look like a dreamy princess from a fairy tale. Carrie Bradshaw in “Sexy and the City” may not have been the best at money management, as she lives a ridiculously lavish Upper East Side life outside of her means, but Sarah Jessica Parker definitely knows how to invest well in amazing couture pieces in real life.

Daryl Hannah

In 1988, Daryl Hannah brought back the popularity of the classic elbow-length gloves when she wore it together with her gold, figure-hugging cocktail dress to the Oscar Awards. Her overall vintage look made her seem like a dazzling star from Hollywood’s Golden Age, and it easily became one of the best Oscar red carpet looks of all time. Since then, many have come to recreate her look. She may no longer be visible in movies these days, but during her active years as an actress, she worked alongside big names such as Robert Redford in the film “Legal Eagles”, where Robert played a district attorney helping out Daryl’s character, who was accused of attempting to steal a painting from a millionaire.

Salma Hayek

Actress Salma Hayek made a huge statement at the 2008 Oscars when she appeared in a purple Gucci by Alessandro Michele gown. In the midst of all-black dress code for the night in honor of the Time’s Up and #MeToo movements, she added a pop of color to the event. Salma Hayek elevated her look with a ton of crystals, capping off her look with diamond chandelier earrings and a diamond ring by jeweler Harry Winston. Her jewelry alone amounted to a jaw-dropping $4.2 million, and we can only assume that her bling was covered by a good insurance plan.