It was the halcyon days of 2018 and the pop singer and fashion icon wore a pair of Uggs to — where else? — the Coachella music festival.
Not your average pair, like the classic boots made famous by a Juicy Couture-clad Lindsay Lohan at the height of her Us Weekly fame in the early aughts. This pair was a collaboration with the Belgian designer Glenn Martens of the avant-garde label Y/Project, who exploded the ostentatiously unsexy style to Brobdingnagian proportions, yielding a version that was high-heeled, slouchy and reached well above mid-thigh. A picture of Rihanna in the wader-like footwear amassed more than 3.3 million likes on Instagram, and even Vogue couldn’t resist their strange allure.
“The C.F.O. was not super-excited about them,” Andrea O’Donnell, the Ugg brand president, recalled. After seeing a CNN news segment of the Y/Project runway show in which they were unveiled, “he came in and said, ‘Tell me that I didn’t see thigh-high boots, on a catwalk, worn by a man,’” she said, laughing.
Ms. O’Donnell had been hired in 2016 to help reposition the brand with consumers who associated Ugg with the classic boot in its purest form: shin-high, slip-on, mocha brown and lined in sheepskin. It was a casual style, to be worn with yoga pants while running errands. Ugg wanted to widen its image to encompass more fashion-forward associations.
And Ugg had lost its luster. Once the boot du jour for carefree socialites and off-duty starlets, it had become part of the uniform of a certain upwardly mobile consumer with bland bourgeoisie taste. The label was hardly the first to experience this trajectory. It’s a common one in fashion: Things that once had an air of exclusivity and mystique are then fully absorbed by the culture. Uggs were beloved but mass market.
Ms. O’Donnell, who came from the luxury department store Lane Crawford, moved to Santa Barbara, Calif., where Deckers, the Ugg parent company, is based, and got down to work, initiating a series of high-profile collaborations to inject some glamour into the label.