1. Grammy award winning singer and style icon Nelly Furtado reviews her best and worst fashion moments and reveals which of her outfits she'd like to keep as an heirloom for her daughter, and which outfits she'd just as soon leave in the closet, when we ask her "What Were U Thinking?"

More On Nelly's Style

  1. Nelly reveals the designers responsible for her "fun, funky, and casual outfit."

  2. Nelly explains how one of her biggest hits inspired this insane bird outfit!

  1. From funky folk to sexy glam, see how Nelly’s style has evolved in our photo recap!

  2. Take a look back at the statement-making outfits Nelly's rocked on stage.

  1. Nelly’s stylist AND designer Charlene Roxborough chats about the style of her long-time client.

  2. Which of Nelly's looks best fits your personality? Take the quiz and find out!

About Nelly Furtado

What would happen if we took your favorite fashionable celebs, showed them five outfits they've worn out in public over the years, and asked them "What Were U Thinking?" You're about to find out!

This time, we're asking Nelly Furtado. From "I'm Like a Bird" to "Promiscuous Girl" to "Mi Plan" Nelly Furtado has been skillfully changing her look to reflect the mood of each of her hit albums. When Nelly first burst onto the scene in 2000 with her album "Whoa, Nelly!" everyone stood up and took notice. Here was a young woman with tremendous talent – a beautiful voice, a skilled songwriter, and very easy on the eyes. But Nelly was still a kid, and her fashion sense hadn't totally evolved yet to where she could rock loads of different styles. Instead, Nelly tried to brand herself so that the public would recognize her whether they knew her name and face or not. She would get sent loads of clothes by Miss Sixty and Fornarina and basically wore a uniform of a tank-top, jeans, sneakers, hoop earrings, and wristbands. Until of course, she got the news that she was heading to the Grammy Awards, where she would eventually win Best Female Pop Vocal Performance for her song "I'm Like a Bird." After choosing a gorgeous white Armani dress, Nelly wound up on best dressed lists everywhere, and everyone began to see the girl in the jeans and tank tops emerge into a beautiful fashionable woman.

After that, Nelly began to have fun with her fashion choices. She took on a folk/hippie-esque look to promote and perform in support of her second album "Folklore." The album featured a mismash of different styles of music, musicians, and instruments. Nelly tried hard, but the album didn't strike a chord with the public and the critics the way "Whoa, Nelly!" did. So it was time for a major change a few years later, on her mega-smash album "Loose." Nelly took on the persona of a super sexy, urban "Promiscuous Girl," which was the name of the hit single she made with super producer Timbaland. During this period she always wore slinky skirts, long sleek hair, and projected an ultra-fashionable hip-hop vibe. To some of her earlier fans, Nelly had changed her look and persona so drastically from the sweet little girl with a heart of gold that they couldn't go along with it – but Nelly just persisted, and in the end she was proved right. Her new style brought her a whole new audience of men and women.

Now with "Mi Plan," Nelly's new sure-to-be-a-hit Spanish-language album, she's taking a distinctively Latin look. Nelly who has Portugese roots, is no stranger to this style – and we can't wait to see what looks she's gonna come up with for this tour! No matter what her musical style is, Nelly's fashion is always there as a complement and always on point. And that's what makes her a true fashion icon.

Past Guests

  1. We asked Jessica Szohr 'What Were U Thinking?' on October 21. Watch the episode now!

  2. We asked Ashley Greene 'What Were U Thinking?' on October 12. Watch the episode now!

  3. We asked Kim Kardashian 'What Were U Thinking?' on September 21. Watch the episode now!

  4. We asked Kristin Cavallari 'What Were U Thinking?' on September 9. Watch the episode now!

  5. We asked Keri Hilson 'What Were U Thinking?' on August 24. Watch the episode now!

  6. We asked Adrienne Bailon 'What Were U Thinking?' on August 10. Watch the episode now!

  7. We asked Kelly Osbourne 'What Were U Thinking?' on July 27. Watch the episode now!