Before Ariana Grande wowed the world with her Glinda-inspired fashion moments, she was best known for her signature high ponytail paired with oversized sweaters and boots. Now, she’s opening up about the unexpected reason behind that iconic baggy look she wore for so many years.
The Wicked actress recently sat down with Vogue to revisit 21 past fashion moments, reflecting candidly on a particularly vulnerable period in her life between 2017 and 2018. While looking at a photo of herself leaving her former New York City apartment in an oversized black sweater, matching thigh-high boots, a green purse wrapped around her waist, and a high ponytail, she admitted, “This was a very strange time in my life.”
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Ariana Grande Reveals Why She Used to Wear Oversized Sweaters and Boots All The Time
“I was processing a lot, and I always wanted to hide away in something really cozy. But I remember that the boots still made me feel c—t,” she explained.
The 32-year-old went on to share that fashion simply wasn’t a priority at the time. “I genuinely, at the time, did not have the mental energy to consider clothing. So, the easiest thing for me was to throw on a sweatshirt and a c—ty boot and that was how it happened,” she said, before adding as she turned to the next look, “I’m sorry to say it, this was just the honest truth.”
Between 2017 and 2018, the singer went through one of the most challenging and transformative chapters of her life and career—one defined by unimaginable tragedy, intense public scrutiny, and personal growth.
In early 2017, Grande was in the midst of touring her third studio album, Dangerous Woman, when tragedy struck. On May 22, 2017, a suicide bomber detonated an explosive in the foyer of Manchester Arena in England as fans were leaving her concert, killing 22 people and injuring hundreds. Grande later spoke openly about developing PTSD and severe anxiety in the aftermath of the attack. Shortly after, she shared a heartbreaking message on X, writing, “broken. from the bottom of my heart, i am so so sorry. i don't have words,” while her team released a statement mourning the lives lost.
Ariana Grande's Tumultous 2017 and 2018
Less than two weeks later, on June 4, 2017, Grande returned to Manchester to host the One Love Manchester benefit concert, raising millions of dollars for victims and their families. Nearly a year later, in April 2018, she released “No Tears Left To Cry,” her first single since the bombing, signaling resilience and a desire to move forward.
Her personal life soon unfolded under intense public attention. In May 2018, Grande began dating comedian and Saturday Night Live star Pete Davidson, and the two became engaged just weeks later. However, in September 2018, tragedy struck again when her former boyfriend, rapper Mac Miller, died from an accidental overdose. Grande paid tribute to him as her “dearest friend,” publicly grieving the loss.
By October 2018, amid overwhelming grief, she ended her engagement to Davidson. Just weeks later, in November 2018, she released the record-breaking single “Thank U, Next,” a candid reflection on love, loss, and healing.
