If award show newbies need inspiration for the impending awards show season, there's a smarter source than Rachel Zoe and company. The new guard should turn to the few true originals who still break fashion rules (yet still own their looks) whenever the flashbulbs pop.

"There are two points in your life when you can take risks: when you're very young, and when you're older, because you've lived through everything," says celebrity stylist Phillip Bloch. "Those women are kind of 'been there, done that.'"

In his forthcoming book, "The Shopping Diet" Bloch celebrates women of a certain age who choose to grow old disgracefully. "She's the kind of woman who has traveled the world, and picks up things along the way so they become part of who she is. It's not just her wardrobe but her medals of honor." These women are more devil-may-care than "Devil Wears Prada."

"Anytime a woman expresses who she is on the red carpet, I applaud it," adds Rob Zangardi, whose client roster includes Rihanna and Rachel McAdams. "And these women who don't play it safe? They're an inspiration to the younger stars to take chances. And as a stylist, I appreciate that." (Translation: maybe Zangardi won't have to call in so many snooze-inducing LBDs next year.)

This awards season, some of the prissier Fashion Police may class these women as repeat offenders, but the red carpet would be dull without them (not to mention that Joan Rivers and co. would be out of a job). It may be easy to pillory fashion risk takers of a certain age, but it's through visionaries – whether YSL's trouser suit or Rudi Gernreich's monokini - that fashion advances.

We've spotlit our ten favorite fashion outliers and asked our two fashion savants to examine what makes them true originals.