Lifestyle Style Harry Styles Dresses as Dorothy from 'The Wizard Of Oz' During Halloween-Themed Concert in N.Y.C. Harry Styles also added his own rendition of "Somewhere Over the Rainbow" to his setlist during his concert at Madison Square Garden By Nicholas Rice Nicholas Rice Instagram Twitter Nicholas Rice is a Staff Editor for PEOPLE Magazine. He began working with the brand as an Editorial Intern in early 2020, before later transitioning to a freelance role, and then staff positions soon after. Nicholas writes and edits anywhere between 7 to 9 stories per day on average for PEOPLE, spanning across each vertical the brand covers. Nicholas has previous work experience with Billboard, POPSUGAR, Bustle and Elite Daily. When not working, Nicholas can be found playing with his 5 dogs, listening to pop music or eating mozzarella sticks. People Editorial Guidelines Published on October 31, 2021 11:15 AM Share Tweet Pin Email Photo: 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. For more on Harry Styles' Dorothy Halloween costume and other top stories, listen below to our daily podcast PEOPLE Every Day. 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." Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer, from juicy celebrity news to compelling human interest stories. Theo Wargo/Getty Matt Damon Says He 'Knew Every Word to Every Song' at the Harry Styles Concert with His Daughters 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."