Not all fashions withstand the test of time, but these Oscar gowns, both classic and innovative, have held up over the years. It’s hard to say what about a dress makes it a victim to a passing fad, or makes it feel chic no matter how many decades have passed. But some select dresses that floated down Hollywood’s biggest red carpet have been cemented into pop culture history.Of course, that should be a goal when picking out a gown for the biggest night in movies — you want it to be timeless and sophisticated; a dress that will be looked back on and revered. While each of the following picks are jaw dropping and gorgeous, the selections become all the more interesting when you learn just how much time and effort went into choosing the dresses. Some starlets decided to switch dresses minutes before hopping into the limo and racing to the red carpet; others had two versions made just in case they didn’t like the original. Some dresses were so sexy that the actresses got typecast as sex idols, while others were straight off of the catwalk from Paris Couture Fashion Week. The following list of gowns have held up flawlessly over the years. From Angelina Jolie to Gwyneth Paltrow, Anne Hathaway to Penelope Cruz, check out some of the most gorgeous Oscar dresses to grace the red carpet since 2000.