Harry Styles also added his own rendition of "Somewhere Over the Rainbow" to his setlist during his concert at Madison Square Garden
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Harry Styles performs, in Dorothy from "The Wizard of Oz" costume, with Toto dog onstage at Harry Styles "Harryween" Fancy Dress Party at Madison Square Garden on October 30, 2021 in New York City.
Credit: Theo Wargo/Getty

Harry Styles channeled Dorothy Gale this Halloween season.

On Saturday evening, the 27-year-old singer took part in the first of his two Halloween-themed shows at New York City's Madison Square Garden, where he dressed up and performed on stage as Judy Garland's iconic character from 1939's The Wizard Of Oz.

Wearing a blue and white dress reminiscent of the one that Garland wore as Dorothy in the popular film, Styles completed his look with rosy red cheeks, red tights and a matching bow in his hair — alongside a pair of ruby red Gucci slippers, of course!

While Styles performed, a picnic basket and a fake dog meant to look just like Dorothy's Toto from the movie also sat beside the former One Direction member onstage.

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And staying true to character, Styles also sang his own rendition of "Somewhere Over the Rainbow" from The Wizard Of Oz, alongside staple performances of songs already featured on his setlist, including "Watermelon Sugar" and "Golden."

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Harry Styles performs onstage at Harry Styles "Harryween" Fancy Dress Party at Madison Square Garden on October 30, 2021 in New York City.
Credit: Theo Wargo/Getty
Harry Styles performs onstage at Harry Styles "Harryween" Fancy Dress Party at Madison Square Garden on October 30, 2021 in New York City.
Credit: Theo Wargo/Getty

Styles kicked off his delayed Love on Tour concert series in September after he released his second solo album, Fine Line, in December 2019, just a few months before COVID-19 hit the United States.

At each of his tour stops, the singer has dressed in eccentric and colorful outfits, which comes as no surprise given Styles' love for fashion and experimenting with different looks.

Styles, who became the first man to land a solo cover of Vogue when he graced the December 2020 issue in a lace-trimmed dress and tuxedo jacket, previously told the publication that he doesn't like "limiting" himself when it comes to the outfits he chooses to wear.

"Clothes are there to have fun with and experiment with and play with. What's really exciting is that all of these lines are just kind of crumbling away," he told the outlet. "When you take away 'There's clothes for men and there's clothes for women,' once you remove any barriers, obviously you open up the arena in which you can play."

"I'll go in shops sometimes, and I just find myself looking at the women's clothes thinking they're amazing. It's like anything—anytime you're putting barriers up in your own life, you're just limiting yourself," Styles added. "There's so much joy to be had in playing with clothes. I've never really thought too much about what it means—it just becomes this extended part of creating something."