2007: Kate Winslet

Titanic star Kate Winslet is a living legend. While that title gives her some privileges in the industry, it can also bring a certain degree of pressure, especially during red carpet events. Fortunately, the actress has an incredibly talented team of stylists to help her prepare for and rock the Oscars’ red carpet every time!

A moment that fashion enthusiasts will never forget is her 2007 Oscar look from Valentino. Not only did the mint green silk dress land Winslet a spot among that year’s best-dressed actresses, but it also landed her a seat among the most expensively dressed celebrities during the Academy Awards. According to Vanity Fair, Winslet’s Valentino gown cost a staggering $100,000! That’s just the dress. The value of Winslet’s outfit is twice higher if we factor in the Chopard pieces of jewelry and the Bulgari clutch bag. If that doesn’t make an iconic outfit, I don’t know what will.