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18. Rihanna In Giambattista Valli, 2015
Rihanna made it to the top of every best dressed list in 2015 with her Giambattista Valli Spring 2015 Couture gown. The pink cupcake gown was a daydream spun in tulle, and its high empire waist only made the silhouette all the more dramatic. Rihanna skipped out on the Grammys the year prior, so she had to make a memorable entrance. (Especially since she won the CFDA Fashion Icon Award the year prior. She had a reputation to uphold!)

She was the last one to arrive to the red carpet, which only increased the drama of her dress pick. While she worked with stylist Mel Ottenberg at the time, the way she chose her dress was extremely relatable. There were no runway presentations or designer meetings, like you would expect. She told E!'s Ryan Seacrest that when she saw the gown online, she knew she had to wear it for the big event. Couture might not be the same as online shopping Zara, but you have to love the image of Rihanna picking out her Grammy dress while on the couch, with Netflix going in the background.

When Rihanna shared the dress with her stylist, Ottenberg knew it was a winner. "I wanted Rihanna to wear something from the Haute Couture shows in January that nobody else would be thinking about. That dress spoke to me and it spoke to Rihanna, and I just sort of knew that was the one," he told Yahoo! Style. "All I cared about was doing a different silhouette. And nothing safe or minimal. I was more into going for something divisive and more fashion this time."

But Ottenberg knew that cinching the dress wasn't going to be easy. "I was stalking Matthew, the Giambattista PR, within an hour after the show."