Pretty Woman: Julia Roberts Sounds Off on Her Best Red Carpet Looks

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For a self-proclaimed “not fashion-y” person, Julia Roberts has definitely taken her fair share of sartorial risks on the red carpet. There was the oversized men’s Giorgio Armani suit at the 1990 Golden Globes, the Old Hollywood–style blush gown that she co-designed with the Italian couturier for the 2004 Academy Awards, and, more recently, the bright red Dolce & Gabbana mini she donned at the 2013 Toronto Film Festival to promote August: Osage County. While the actress may be most known for her black and white choices, she's also proven time and again that she's not afraid to wear pops of color, and remains one of the stars to watch during awards season.

"I had a very whimsical sense of style," our September cover star told InStyle editor Ariel Foxman, as the actress reflected on her most well-known awards show outfits. "I clearly didn’t care what anybody thought about it." Her advice for tackling the red carpet? "It doesn’t matter how much you dress it up or bejewel it, it’s still you, and I feel like at the end of the day I have to feel like I’m myself." Our 20th anniversary has us feeling pretty nostalgic these days, so in honor of the September issue, we decided to take a walk down memory lane with one of Hollywood's dearest talents. Click through our gallery for Roberts's commentary on her most talked-about red carpet looks.

For more of our interview with Roberts, pick up the September issue of InStyle, on newsstands and available for digital download now.

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GIORGIO ARMANI, 1990

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Roberts made a gender-bending style statement at the 1990 Golden Globes when she arrived in an oversized Giorgio Armani suit, which she picked up off the rack at the store. "I loved the shape of it," she said. "For me, this was the epitome of being dressed up."

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RALPH LAUREN, 1999

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At the 51st Annual Emmy Awards, the front of Roberts's black fitted gown looked covered up, but the back incited oohs and aahs. "The dress was backless," she said. "Actually, it wasn't a whole lot of dress."

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ARMANI, 2001

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The actress looked elegant as ever at the 2001 Golden Globes in a long-sleeve Armani sheath. "It's simple and beautiful," she said. "I love those dresses that you put on and there's no fussing with it."

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VALENTINO, 2001

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Later that same year, Roberts stunned audiences at the 73rd Annual Academy Awards in a floor-length, black and white Valentino gown. "The Saturday before the show, I had lots of options but still didn't know what I was going to wear," she said. "The stylist pulled this out and said, 'I found this in the vault at Valentino and thought you'd like it.' I think it had been worn only once, nine years earlier, and they'd stored it away. It fit me perfectly." That same evening, Roberts took home a best actress statue for her role in Erin Brockovich.

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GIORGIO ARMANI, 2004

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At the 76th Annual Academy Awards, the actress donned yet another figure-flattering Giorgio Armani number, which she co-designed with the man himself. "People thought it was a 50-bazillion-dollar diamond brooch, but it was just a little costume pin!" she said.

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DOLCE & GABBANA, 2013

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Roberts opted for a pop of color at the August: Osage County première at the 2013 Toronto Film Festival. "That was a really fun night," she said. "I've always loved Dolce & Gabbana because they make things that you zip up and go, 'Done!'"

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DOLCE & GABBANA, 2014

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The actress wowed in another DampG frock, which she made her own by adding another layer on top. "I didn't know if I'd feel comfortable in the dress alone—I felt super-naked," she said. "My stylist, Elizabeth Stewart, knows I love tuxedo looks, so she smartly suggested we tailor a white shirt to wear under it. And it worked!"

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Pretty Woman: InStyle’s September Cover Star Julia Roberts on Her Best Red Carpet Looks