When you see an oversized sweatshirt, a high ponytail, and thigh-high heeled boots, one name instantly comes to mind: Ariana Grande.
Over the last decade, Grande has not only dominated the charts with her eight Billboard Hot 100 No. 1 singles and five Billboard 200-topping albums — including Sweetener (2018), thank u, next (2019), and Positions (2020) — but she has also made waves with her evolving style and signature glam.
When she first emerged with hits like “The Way” featuring Mac Miller and “Baby I” in 2013, Grande channeled the vintage charm of her debut album Yours Truly, sporting ’50s-inspired dresses, a wavy half-up-half-down ponytail, and sky-high pumps, a striking contrast to the fiery red hair she wore during her Nickelodeon days.
By 2014, following the release of her smash-hit album My Everything, she embraced a new look with cat ears, an even higher ponytail, revealing onstage leotards, and the now-iconic oversized sweatshirt paired with thigh-high boots. Then came her Dangerous Woman era in 2016, which marked another shift. With edgier, more provocative lyrics, Grande traded her cat ears for latex bunny ears, along with bustiers, slacks, and bold black chokers.
When she unveiled the Grammy-winning Sweetener, fans were surprised to see her rocking platinum blonde hair. Her wardrobe didn’t change drastically, but by the time she released thank u, next the following year, her style had grown darker in tone, both in color palettes and overall mood. For Positions, she embraced ’60s-inspired glamour, complete with honey-brown hair, floral designs, and voluminous, retro hairstyles.
As Grande prepares to step into the next phase of her career with her upcoming album Eternal Sunshine and the highly anticipated Wicked films, let’s take a look back at how her style has transformed over the years.
#1. 2009
Ariana Grande made a statement at the 2009 AFI Festival, arriving in a forest green dress that perfectly complemented her fiery red hair. This early look showcased her playful yet bold style, hinting at the fashion evolution that would follow as her career skyrocketed.
#2. 2009
At Variety’s 3rd Annual Power of Youth Event on December 5, 2009, at Paramount Studios in Los Angeles, the “Tattooed Heart” singer embraced a more edgy look. Ariana Grande rocked a leather skirt paired with a floral top, blending softness and boldness, and offering a glimpse of her evolving style.
#3. 2010
Ariana Grande dazzles in a floral romper paired with sky-high pumps at the Make A Wish Foundation event, hosted by Kevin and Steffiana James, at Santa Monica Pier on March 14, 2010, in Santa Monica, California. Her chic
#4. 2010
Ariana Grande showcased her fiery red hair in a sleek, straight style and rocked a figure-hugging nude-tone bandage dress at the 2010 MTV Movie Awards, turning heads with her effortlessly chic look.
#5. 2011
Ariana Grande embraced a laid-back style with a slicked-back ponytail, denim jeans, and a tan tank top during her visit to Broadway Names With Julie James on SiriusXM’s On Broadway channel at the SiriusXM Studio.
#6. 2011
Ariana Grande dazzled at the Malan Breton Spring 2012 fashion show, wearing a glamorous dress featuring a sparkling, bedazzled bustier.
#7. 2012
Ariana Grande made a chic entrance at 102.7 KIIS FM’s Wango Tango, wearing a strapless floral dress paired with nude pumps.
#8. 2012
Ariana Grande embraces her Yours Truly aesthetic with a floral, light blue two-piece outfit at Variety’s Power of Youth event.
#9. 2012
At the premiere of The Twilight Saga: Breaking Dawn – Part 2, Ariana Grande showcases a stunning transformation in a beautiful floral full-length gown, complemented by a sleek, dark brown ponytail.
#10. 2013
Ariana Grande looks ethereal in a delicate pink semi-sheer dress at the 2013 Radio Disney Music Awards.
#11. 2013
While performing at the 2013 MTV Video Music Awards, Ariana Grande embraced her brunette roots in a dazzling sparkly purple ensemble.
#12. 2013
As if her performance of “Tattooed Heart” wasn’t already a showstopper, Ariana Grande secured her “star is born” moment at the 2013 American Music Awards, where she won New Artist of the Year, stunning in a sparkling red evening gown.
#13. 2014
At the following year’s American Music Awards, Ariana Grande made a bold statement with swooped bangs, donning a racy black lace gown. During the event, she performed a medley of her biggest hits from My Everything, including “Problem” and “Love Me Harder.”
#14. 2014
Ariana Grande radiates My Everything vibes in this eye-catching snowflake-themed two-piece leotard during her performance at the 2014 Hot 99.5 Jingle Ball.
#15. 2015
At the 2015 Grammy Awards, Ariana Grande dazzled in a stunning white and silver gown, complemented by her sleek dark brown high ponytail, as she celebrated her dual nominations.
#16. 2015
Ariana Grande delivered a quintessential performance at Madison Square Garden in 2015, rocking a black leotard, thigh-high boots, a half-up, half-down ponytail, and iconic cat ears—truly a winning look!
#17. 2016
To kick off the 2016 GMA Summer Concert Series, the “Into You” singer sported a flannel tied around denim shorts, paired with thigh-high boots and a sparkling black bustier for a chic, edgy look.
#18. 2016
At the 2016 VMAs, the “Side to Side” singer embraced her slacks era, donning a daring black lace crop top paired with sleek black pants. While she may have lost all five of her nominations that night, she certainly made a stylish statement!
#19. 2016
The multihyphenate made a bold style change with a fresh set of bangs and baggy stone-gray cargo pants during her appearance on The Tonight Show Starring Jimmy Fallon.
#20. 2016
Grande exuded femme fatale vibes during her Dangerous Woman Tour, rocking a jet-black ensemble that featured thigh-high boots, an oversized puffer jacket, and a sleek black leotard.
#21. 2018
At the 2018 Billboard Women in Music Awards, where she was celebrated as Woman of the Year, Grande showcased her signature high ponytail, pairing it with a strapless lavender dress, chic mauve boots, and elegant diamond jewelry.
#22. 2018
To debut the lead single “No Tears Left to Cry” from Sweetener on The Tonight Show Starring Jimmy Fallon, Grande showcased a wavy blonde ponytail and a vibrant pink dress.
#23. 2019
During her 2019 headlining set at Coachella, affectionately dubbed “Arichella” by fans, Grande fully embraced her pop star persona in a striking plum outfit featuring dramatic oversized shoulders and a bare midriff.
#24. 2020
At the 2020 Grammys, where her thank u, next album was nominated for four awards but did not win, Grande made a stunning statement in an ethereal gray Giambattista Valli Haute Couture gown.
The dress featured a tiered tulle skirt, beautifully complemented by a bumped two-tone ponytail. She arrived at the 62nd Annual GRAMMY Awards held at the Staples Center in Los Angeles on January 26, 2020.
#25. 2020
For the official photoshoot promoting her 2020 album Positions—which debuted at number one on the Billboard 200 and featured the chart-topping title track—Ariana Grande channeled ’60s vibes with a stunning jade green two-piece ensemble.
She accessorized with vibrant green flower earrings and styled her hair in a high, eye-catching updo that reached for the sky.
#26. 2021
For the promotional photos announcing her role as a judge on The Voice, Ariana Grande dazzled in a flapper-inspired black fringe dress paired with matching black pumps, perfectly capturing the glamour of the era.
#27. 2021
At the 2021 iHeartRadio Music Awards, where she made her performance debut of “Save Your Tears (Remix)” alongside The Weeknd, Ariana Grande stunned in a silky eggplant Rat and Boa crop top paired with a floor-length skirt, showcasing her elegant yet bold style.
#28. 2021
In these promotional photos for The Voice, Ariana Grande opted for earth tones to create a softer vibe. She paired her dark brown ponytail with a green-brown top, khaki slacks, and sparkly heels, blending elegance with a relaxed style.
#29. 2023
While attending the Wimbledon Tennis Championships, the “7 rings” singer embraced a preppy look with a stylish ensemble featuring black pointed pumps, a gray short-sleeve knitted crop top, and a coordinating A-line midi skirt.
#30. 2023
Divas gonna diva! While out and about in NYC, Grande showcased her elegance in a classy black evening gown, complemented by a sleek blonde ponytail and a sultry red lip as she signed autographs for her fans.
#31. 2024
At the start of 2024, Ariana Grande launched her Eternal Sunshine era with the Hot 100 chart-topping single “Yes, And?” In the music video, which pays homage to Paula Abdul and Bob Fosse, Grande dazzled in a striking black and white Rodarte bodysuit.
