Harry styles
OCTOBER 30: Harry Styles performs onstage at Harry Styles “Harryween” Fancy Dress Party at Madison Square Garden on October 30, 2021 in New York City. (Photo by Theo Wargo/Getty Images for HS)

Harry Styles has undoubtedly been pulling off some iconic fashion moments (peruse) since he began his second Love On Tour stretch in September. For his wardrobe, the singer continues his long-standing relationship with Gucci’s creative director Alessandro Michele wearing looks from printed suits to sequined vests designed by the luxury Italian house. 

Being the hardcore Halloween fan he is, it was the 27-year-old singer’s Madison Square Garden concert (dubbed Harryween) Saturday evening that really showed his love for fashion. Clicking his bedazzled ruby slippers three times, Styles transforms himself into Judy Garland’s iconic character Dorothy from the 1939’s classic, The Wizard Of Oz. The former One Direction member wore a blue and white gingham puff sleeve shirt dress nearly identical to the one worn by Dorothy in the film–naturally, his was custom Gucci.

Harry styles
Harry Styles and his band wearing Gucci for the “Harryween”

Styles missed no details when it came to the look. He paired the look with red tights and a matching bow in his hair. Even a plush dog in a picnic basket resembled Dorothy’s puppy Toto that sat on the side as he performed throughout the night. Harry wasn’t alone in his over-the-top costume; The Wizard of Oz theme was a group affair. His band filled out the remainder of the film’s cast, including the Good Witch, the Wicked Witch, Scarecrow, Tin Man, The Wizard of Oz, and The Cowardly Lion all in–you guessed it, Gucci.

Styles stayed in character performing his own rendition of “Somewhere Over the Rainbow” from The Wizard Of Oz, alongside his lineup of hit songs like Watermelon Sugar, really bringing the moment full circle.