20 of Ariana Grande's most daring looks

Ariana Grande 2012 Emmy red carpet look was a vivacious backless halter gown with a flowing skirt.

Grande's transition from an age-appropriate teen sensation to a daring pop sensation was slow and steady. Many of Grande's early looks seemed like she was trying to define her style, likely explaining her experimentation with statement colors like crimson here.

Her 2012 Emmys red carpet gown was the beginning of her halter dress era, which persisted for years.

Ariana Grande rocking a neon-lit two-piece outfit back in 2013 was an epic fashion moment for her.

Around this time, Grande had just released her first album, and she was finding her own style as a budding pop-star.

The bright neon-lit outfit that she wore to perform at the 2013 Country Music Awards alongside Little Big Town was unique, and solidified her as an artist to watch, and potential style icon.

Watch the performance here.

Ariana Grande loves a good two-piece, and her gold performance outfit at the 2014 American Music Awards is one of the most eye-catching two-pieces she's ever worn.

The golden outfit sparkled under the stage lights, illuminating Grande's golden hues and added substantially to her style evolution. 

Watch the performance here.

A leather Moschino minidress looked top-tier on Grande at the 2014 MTV Video Music Awards.

In the beginning of Grande's career, she was a sweet Nickelodeon teen sensation, but soon after her intro into the music scene, she blossomed into a full-fledged woman.

After transitioning from kid-star to pop-star, Grande began experimenting with her look, and grew more daring.

Her leather Moschino look at the 2014 MTV VMAs was one of her first daring red-carpet looks, separating her from her former child-star image tastefully. She paired it with matching thigh-high leather boots, adding to the drama.

The 2014 Bambi Awards showcased Ariana Grande in a sultry light, with her sheer bodysuit and thigh-high boots.

"Cutely seductive" is how we'd describe Grande's outfit.

The dress that Grande wore to the 2014 American Music Awards showed just enough skin through its patterned lace.

This look, designed by MT Costello, was pure elegance, and was very much on theme for the typical looks that was popular for Grande around this time: sheer dresses, red lips, and high ponies.

Watch the performance with The Weeknd here.

Grande on the 2015 Grammys red carpet was a bold moment in her fashion evolution, as she wore a white gown with a daring slit and back cutouts.

Around the mid-2010s, Grande's red carpet looks often consisted of neutral colors and cutouts.

This white and metallic Versace dress Grande wore to the 2015 Grammys showed quite a bit of skin, and was the beginning of her experimentation with being more daring.

Grande's gown she performed in at the 2015 Grammys also had daring cutouts, this time a keyhole cutout on her torso.

Sophisticated keyhole gowns with a moderate amount of cleavage were one of Grande's signature looks during this stage of her career.

Watch the performance here.

At the 2016 Billboard Music Awards, Grande wore a black gown with another thigh-high slit and cutouts, this time with electric-blue accents.

Some of Ariana Grande's best red carpet looks involve her in sleek cutout dresses, like the one she wore to the 2016 Billboard Music Awards.

Once again, she made Versace proud when she wore their haute couture section of their collection, Atelier Versace, to the 2016 Billboard Music Awards.

The lacy black off-the-shoulder Alexander Wang crop top and matching black high-waisted slacks she wore to the 2016 MTV Video Music Awards were a sassy approach to business-casual.

Straying away from gowns and tight-fitting dresses, Grande popped up at the 2016 MTV VMAs celebrity carpet in a classy two-piece look that managed to balance both the sophisticated slacks and the on-trend tiny crop top.

At the 2016 American Music Awards, Grande's red carpet look consisted of a lacy spaghetti-strap bustier and white Alexander McQueen slacks.

When Ariana Grande finds a style that works for her she loves to stick to it, as evidenced by her back-to-back high-waisted pants looks.

The ruffled trench coat gown and diamond choker that Grande wore during the closing sequence of her 2017 "Dangerous Woman" tour is simply iconic.

An edgier side of Grande was displayed during her 2017 "Dangerous Woman" tour.

Grande's tour fashion designer and stylist, Bryan Hearns and Law Roach, produced looks for her that were an amalgamation of street fashion and haute couture, taking Grande's style to a new level.

Taking a futuristic approach to her fashion, Grande went to the 2018 MTV Video Music Awards dressed in a Wonder Woman-inspired metallic minidress and gunmetal-gray thigh-high boots.

Grande's warrior-like 2016 MTV VMAs look consisted of a silver strapless bustier, a pair of metallic biker shorts (which were under her metallic miniskirt), and thigh-high Le Silla boots. She looked ready for combat.

At the 2018 Billboard Women in Music Awards Ariana Grande glowed in a lavender dress with a bubble skirt with matching over-the-knee suede boots.

The Christian Siriano dress worn by Grande at the 2018 Billboard Women in Music Awards was a more mature version of looks Grande used to wear when she was still coming up the ranks as a Nickelodeon star.

Grande is great at conveying innocent beauty in her looks, and the ultra-short, ultra-feminine pink dress she wore on a 2018 episode of "The Tonight Show With Jimmy Fallon" adorably proved that.

Grande's spaghetti-strapped cotton-candy-colored Cecilie Bahnsen babydoll dress and her signature suede thigh-high Le Silla boots is one of her most standout styles.

One of Ariana Grande's most ethereal and adventurous looks is her 2018 Met Gala gown, which paid homage to the Catholic church and its influence on fashion.

Grande did the custom Vera Wang dress so much justice that it's one of her best and most daring looks to date, given the structure and design of the Met Gala gown.

Although Grande's stylist Law Roach kept her aligned with the 2018 Met Gala theme, he also intentionally made the overall look still Grande-appropriate. 

"It was just all about romance with her," Law Roach told Women's Wear Daily. "There is a bit of drama there, there is a silhouette that we are used to seeing her in but, of course, more elevated and more appropriate for the event. It is very recognizably Ariana Grande, for sure."

Stepping onto the world stage during her 2019 "Sweetener" tour, Grande wore a monochromatic red bondage-inspired two-piece with matching platform boots.

With input from famed celebrity stylist Law Roach, Grande was able to wear some of her best ensembles on her 2019 "Sweetener" world tour.

"I always like to say if you put anyone behind a screen with a long pony, an A-line skirt, an over-the-knee boot, the first thing that comes to everybody's mind is now Ariana Grande," Roach told People. "I really do think that one of her ponytails will end up in the Smithsonian one day, that's how iconic I believe that ponytail is."

This look specifically consisted of a belted crop top with puffy sleeves, a studded leather skirt, and thigh-high patent leather boots and, of course, her ponytail.

The pretty-in-pink cowgirl outfit that Grande wore for a performance on season 21 "The Voice" would definitely make Dolly Parton proud.

Everything about this look screamed country-chic, and the fabulous monochromatic color scheme was designed by the one-and-only Prabal Gurung. She added a string of pearls, elbow-length gloves, and a white cowboy hat to complete the look.

Grande's peacock-patterned two-piece outfit during season 21 of "The Voice" is one of her chicest looks yet.

Her petite frame was accentuated by both the high-waisted pencil style miniskirt and the long-sleeved bustier crop top featuring padded shoulders.

The vibrant shades of blue and green capture your attention, much like a peacock would.

Grande's choice to wear an outfit designed by Sohee Park is testament to her new daring fashion outlook.

Classified as a new-gen couturier, Sohee Park's designs are vibrantly illustrative pieces inspired by escapism, and best summarized as demi-couture. 

Grande stunned on the 2020 Grammys red carpet in a custom Giambattista Valli ruffled gray ball gown.

At the 2020 Grammys, Grande reached peak excellence in her fashion journey — Insider even named her one of the best-dressed of the night. She looked like total fashion royalty in this gray gown, paired with her signature high ponytail and opera-length gray gloves, styled by Law Roach.

During E!'s 2020 Grammys coverage, correspondent Zanna Roberts Rassi shared that Grande's frequent fashion collaborator and stylist Roach told her that "the moment [Ariana] tried this on, he burst into tears and [Grande] was like, 'well, this is the dress then.'"