10 Award Winners Red Carpet Recap

Sandra Bullock, in Marchesa, Academy Awards 2010

She might be one of the highest paid actresses in Hollywood and a two-time Oscar nominee, but Bullock is not a risk-taker when it comes to dressing for red-carpet events. In keeping with her low-key approach to style, for the 2010 Oscars, where she won the Best Actress Academy Award for The Blind Side, she opted for a simple metallic-coloured gown. The shimmer might have been subtle, but she radiated elegance.

At just 10 years old, the daughter of Ryan O’Neal won Best Supporting Actress Oscar for her role in Paper Moon. She could have done the Shirley Temple thing and dressed in a sweet frilly dress but opted for a little satin tuxedo worn with gold platform shoes. She later said she was inspired by Bianca Jagger, who was dating her father at the time. The tux was perfect for her tomboy looks, and she appeared cool and confident as she marched up to the podium, made a six-second speech and accepted her award.

How do you dress for a high-profile event when you’re pregnant and keep it looking elegant and sophisticated? Portman positively looked blooming in a blush pink gown that looked effortless. And it hit the right notes with a single blood red rose appliqué, which put a single exclamation point on this masterly maternity gown.

This partially sheer gown was daring at the time. But the actress, with her fit and toned body, was known for wearing outfits that showed off her fantastic figure. The design by Lebanese designer Elie Saab was a perfect blend of Hollywood glam and sexy siren. Berry not only made history that night by being the first black actress to take home a Best Actress Oscar, for her role in Monster’s Ball, but this daring fashion choice also put the designer on the fashion map.

The stunning beauty – with serious acting chops, having won the Best Actress award for her role in Monster – channelled old-world Hollywood but with a modern edge. Her hair, soft cascading waves, was classic screen siren while her gown, a traditional fishtail style – shimmered delicately and revealed an exposed back. It was the right amount of sexy that showcased her youthful golden looks.

The sugary pink gown seemed like a good idea for America’s sweetheart to wear to the Oscars, where she took home the trophy for her role in Shakespeare in Love. But the ill-fitting bodice and overly long spaghetti straps did her no justice and made her appear awkward and ill at ease on her big night.

This legendary actress has been nominated an astonishing 19 times for an Oscar over the last 37 years. She has won three. Her latest was for her role as Margaret Thatcher in The Iron Lady. The stunning gold gown with a daring neckline was worthy of this accomplished actress.

While this gown was spectacular, it felt overpowering on the actress, whose demeanor is youthful, easy-going and carefree. A seriously dramatic gown that caused her to trip and fall as she went up to the podium to accept her Oscar that night.

This dress was deemed one of the most iconic red-carpet dresses by many fashion critics. Even the designer, Valentino, declared it a high point in his career when Roberts wore it and won the Oscar for her role in Erin Brockovich. While the graphic black and white design did indeed look stunning on Roberts that night, the only fail was her gigantic hairdo, which looked matronly opposite the modern clean lines of the dress.

The legend has been known to break all sorts of fashion rules. Way before Beyoncé, Rihanna and Kim Kardashian were wearing see-through gowns, Cher caused jaws to drop – including sending Jane Fonda into a laughing fit – when she wore this beaded number to accept her Oscar for her role in Moonstruck. Somehow it worked for Cher, and she looked flawless that night. Looking back at it now, it still looks like a fashion risk that was successful.