Popsugar Entertainment Music Covers Harry Styles Covers "Somewhere Over the Rainbow" as Dorothy Harry Styles’s Dorothy Costume Is Almost as Iconic as His Britney Spears "Toxic" Cover 1 November 2021 by Victoria Messina Image Source: Getty / Theo Wargo My No.1 regret in life is not splurging on tickets for one of Harry Styles's Harryween concerts. The singer spent Halloween weekend performing back-to-back Love on Tour shows at Madison Square Garden in New York City, and goodness gracious, did he pull out all the stops for both gigs. On night one, Styles put his sheer lack of toxic masculinity on full display while dressing as Dorothy from The Wizard of Oz — glittery ruby slippers, short blue dress, hair bow, and all. After singing hits from his usual setlist, including "Golden", "Watermelon Sugar", and "Kiwi", he went off script and slipped in a dreamy cover of "Somewhere Over the Rainbow" to really make fans swoon. The very next evening, Styles returned to the same stage but swapped out his Dorothy getup for a lacy clown-inspired costume and face jewels. He wound up treating fans to a performance of his unreleased track "Medicine", as well as a sexy and unexpected cover of — are you ready for this? — Britney Spears's "Toxic". If you're ready for your Styles obsession to grow tenfold, check out all the Harryween photos and videos ahead, and then catch up on what other stars wore to celebrate the spooky holiday this year. Related: Wow, Jungkook's Cover of Harry Styles's "Falling" Sounds Like a Little Slice of Heaven Harry Styles Dressed as Dorothy For Harryween Night One Image Source: Getty / Theo Wargo 1 / 17 Image Source: Getty / Theo Wargo 2 / 17 Image Source: Getty / Theo Wargo 3 / 17 Harry Styles Singing "Somewhere Over the Rainbow" at Harryween Night One 4 / 17 More Videos From Harryween Night One @saintcloudthelabel We’re not in Kansas anymore ♬ original sound - SAINT CLOUD🦋 5 / 17 @saintcloudthelabel He did WHALE! And wait till the end omg the cutest #HARRYSTYLES #harryween ♬ original sound - SAINT CLOUD🦋 6 / 17 @saintcloudthelabel His eyelashes were acting up on him 😂😂 #harryween #harrystyles #laneone ♬ original sound - SAINT CLOUD🦋 7 / 17 @saintcloudthelabel During 1D days did we ever think we’d see Harry singing WMYB in a Dorothy costume? #harrystyles #harryween ♬ original sound - SAINT CLOUD🦋 8 / 17 Harry Styles Dressed as a Clown For Harryween Night Two Image Source: Getty / Kevin Mazur 9 / 17 Image Source: Getty / Kevin Mazur 10 / 17 Image Source: Getty / Kevin Mazur 11 / 17 Harry Styles Singing "Medicine" and "Toxic" at Harryween Night Two 12 / 17 More Videos From Harryween Night Two pic.twitter.com/aoepD1eetY— em (@selftitled) November 1, 2021 13 / 17 @saintcloudthelabel the cutest angel 👼 ♬ original sound - SAINT CLOUD🦋 14 / 17 @saintcloudthelabel We’re addicted to Harry does he know that he’s toxic? THIS WAS EVERYTHING 😭#harryween #harrystyles #TOXIC ♬ original sound - SAINT CLOUD🦋 15 / 17 @saintcloudthelabel “This is called edging” NO HE DID NOT ♬ original sound - SAINT CLOUD🦋 16 / 17 @saintcloudthelabel Ugh I love him sm 🥺 #harryween #harrystyles #wmyb ♬ original sound - SAINT CLOUD🦋 17 / 17 Music CoversCelebrity Halloween CostumesHarry StylesHalloween CostumesHalloweenMusic