Quick—think of Cher at the Oscars. What's the first image that comes to mind? Perhaps the 1986 feathered headdress or the bedazzled and barely there gown from 1988? The bikini-and-sarong luau look from 1974? The singer is known for her all-out style on the red carpet. But—surprise, surprise—she's had some rather lovely and elegant moments too, such as the above beaded slip and shawl from 1984. The pink metallic satin dress she wore to her Academy Awards debut in 1968, meanwhile, was downright demure—by Cher standards, at least. 

Now this is how glamour is done. There's no shortage of allure on the red carpet, but Lauren Hutton in a draped goddess gown—by the high priest of Seventies glamour, Halston—and a fur chubby at the 1975 Oscars sets the bar. Her hair is natural; her makeup, fresh-faced… The look is breathtaking in its simplicity. 

High drama when it comes to award-show fashion isn't always a good thing. Just think of all the worst-dressed lists we devour with zeal—those red-carpet fails are heavy on the theatrical. But here's an example of a showstopper done right: Faye Dunaway attending the 1968 Oscars for Bonnie & Clyde in this gothic, extravagantly trimmed outfit. Fun fact: It was designed by Theadora Van Runkle, the costume designer behind Dunaway's trend-sparking wardrobe in that film. 

This one makes the list because it's the dress that launched a thousand memes—not to mention the vogue for soaring, nose-bleed side slits both on and off the runways.