See Ariana Grande's Most Daring Looks of All-Time

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Ariana Grande has become a style icon over the years.

Whether she’s on the stage or on the red carpet, the “Thank U, Next” singer loves to push the fashion limits in daring ensembles. From high heels to cut-out dresses, fans love Grande’s sense of style. In just a few days, Grande is up for nine awards at the 2019 Billboard Music Awards. The 25-year-old singer is nominated for Top Artist, Top Female Artist, Billboard Chart Achievement Award, Top Billboard 200 Artist, Top Hot 100 Artist, Top Streaming Songs Artist, Top Song Sales Artist, Top Radio Songs Artist and Top Social Artist at the May 1 ceremony.

As we gear up for the award show, we’re hoping Grande hits the red carpet and serves another iconic fashion moment, like the one she gave us at the 2016 Billboard Music Awards!

In celebration of her Billboard honors, we’re looking back at Grande’s most daring looks of all time! Let’s take a trip down fashion lane with these style moments!

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Coachella Cool

The Grammy winner hit the Coachella stage in this glittery number during her headlining performance in April 2019.

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Tour Style

Lady in red! The singer took the stage during her opening night concert of her Sweetener World Tour in this stylish red ensemble, complete with red hot boots!

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"Loofah of the Year"

For the Billboard Women in Music 2018 event in December, Grande donned a lavender Christian Siriano dress. “loofah of the year,” Grande captioned a photo of herself in the outfit.

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Wicked Wardrobe

While performing for the TV special, A Very Wicked Halloween: Celebrating 15 Years on Broadway, Grande dressed up in this green number, complete with green lipstick and eye makeup. 

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God Is a Woman

Golden goddess! Grande performed in this golden outfit at the 2018 MTV Video Music Awards.

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Bikini Besties

Grande teamed up with Nicki Minaj for the song “Bed,” both donning bikinis in the track’s music video.

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Met Gala Debut

Grande made her Met Gala debut in May 2018, walking the red carpet in Sistine Chapel-inspired Vera Wang dress. “I’m wearing Vera Wang,” she told E! News on the carpet. “I’m very happy to be her date tonight…this is a painting I’m wearing.”

Shortly before making her debut at the 2018 fashion event, which had the theme “Heavenly Bodies: Fashion and the Catholic Imagination,” Grande hinted at her ethereal dress on Instagram, sharing of picture of Michelangelo‘s The Last Judgement.

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"Gumdrop" Glamour

“I look like a gumdrop, is it OK?” Grande joked with Jimmy Fallon in May 2018 while appearing on The Tonight Show.

In response, the late-night host told the singer she looked like the “most beautiful gumdrop.”

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Surprise Performance

In April 2018, Grande made a surprise appearance at Coachella, performing her song “No Tears Left to Cry” in this purple ensemble.

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Lovely in Lace

Grande donned a lace crop top for the 2016 American Music Awards red carpet, pairing the top with white pants and a snatched ponytail.

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Ponytail Perfection

Grande worked her signature pony in this American Music Awards look in 2016. The artist took the stage at the ceremony to perform “Side to Side” with Nicki Minaj.


Overalls Outfit

While on the red carpet at the Hairspray Live! press junket in Nov. 2016, Grande paired overalls with a bralette.  

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Billboard Beauty

The Nickelodeon alum wore this blue Atelier Versace dress to the Billboard Music Awards in May 2016.

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Grammys Goddess

In Feb. 2015, Grande hit the red carpet at the Grammys in this asymmetrical Versace dress.

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See-Through Sensation

For one of her performances at the American Music Awards in Nov. 2014, Grande donned a see-through lace dress.

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Lady in Red

Grande brought the glamour in this red sequined gown at the 2013 American Music Awards.

Watch E!’s Live From the Red Carpet: The 2019 Billboard Music Awards special on Wednesday, May 1 starting at 6 p.m. followed by the 2019 Billboard Music Awards telecast at 8 p.m. on NBC!

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