9. Anne Hathaway
At the 2011 Academy Awards, Anne Hathaway emerged as the perfect embodiment of Hollywood glamour as she walked the red carpet and hosted the show in a lavish red gown. The pillar-box gown made of silk faille was a Valentino design, and was reportedly worth $80,000. It was a strapless gown that perfectly highlighted her $10 million worth of Tiffany & Co. necklace. She had her signature red lipped smile on all night during which she changed eight times, but the Valentino was the priciest.
8. Jessica Biel
The third actress to slip into a $100,000 worth of dress by Chanel at the 2014 Oscars, and become one of the actresses to wear the most expensive Academy Awards dresses, was Jessica Biel. The embellished blush column gown had a series of silver buttons, to match the silvery subtlety of the shade of the dress, gave a particularly striking look from the back. The strapless piece smoothly framed her form and flowed into a train. She teamed it with Tiffany & Co. Blue Book Collection.
7. Kate Winslet
At the 2007 Academy Awards, Kate Winslet hit the $100,000 mark with the decadent Valentino creation she wore. The vintage one-shoulder dress was of a pleasantly unusual pale sea-foam green shade. The drape around the bodice extended to an over-the-shoulder train, adding to the glamour of the gown which hugged her figure up to the knee, to flare gently below that. The ensemble, complete with a chic up-do, got her voted the best dressed actress at the event by fashion-patrons.
6. Audrey Hepburn
At the 1954 Academy Awards, Audrey Hepburn looked sublime as she stepped on the stage to receive her award for her role in Roman Holiday, appropriately in the customized version of the final dress she wore in the movie. The original design of the ballgown was altered for the event, to cut its bodice straight across at the front, and into a plunging back, including thin straps. Its original cost being unknown, the ivory lace Edith Head creation was auctioned in 2011 for a whopping $131,292.
5. Elizabeth Taylor
In 1999, Elizabeth Taylor became one of the actresses to wear the most expensive Academy Awards dresses, when her 1970 Oscars vintage dress was auctioned for a massive $167,500, though it is unclear as to what the original cost was. The periwinkle and violet chiffon number was an Edith Head creation, and its plunging neckline perfectly accentuated her frame. Her iconic look was completed with violet eye-shadow and a 69-carat diamond necklace, a gift from her husband Richard Burton.