While Winehouse favored retro silhouettes for her stage style, it may come as a surprise that many of her ensembles were not sourced from vintage shops—rather, they were cultivated for her by Winehouse’s costume designer, Naomi Parry. A close friend to Winehouse, Parry began working as the singer’s stylist in 2006, and she wanted to amp up the fashion flavor that Winehouse was already embodying at the time. “Her look had started to develop during her early years in Camden, largely influenced by the characters living there—the rockabillies, punks, ska and indie kids,” Parry has said. (Winehouse’s casual off-duty looks often consisted of simple tanks, paired with skinny jeans and peep-toe pumps.)
For her performances, Parry first began by pulling things for the star that fell in line with her throwback sensibility. At the 2007 Brit Awards, for one, she styled Winehouse in an acid yellow Preen dress with a red heart Moschino bag; Later, she changed into a red and black Armani Privé number plucked from the label’s archives, featuring a ruffled skirt and halter neckline. “No matter what I put her in, Amy was very much the architect of her ultimate appearance,” Parry told the Sydney Morning Herald last year. “It didn’t matter how armed I was with the correct underwear, tit tape, sewing kit, safety pins—she would always add the Amy edge, the imperfection of the look that ultimately was the ingredient that made her unique.” Winehouse’s signature satin ballet flats, for instance, was all Amy.
As Winehouse’s stardom rose, Parry then began creating custom pieces for Winehouse for the stage too. Many of these pieces were displayed in a 2020 at the Grammy Museum, titled Beyond Black: The Style of Amy Winehouse. In 2011, Parry designed several retro mini dresses for Winehouse to wear during her European tour, which ultimately ended up never happening (the singer died in July that year). For her final performance in Belgrade, the singer wore a striped Naomi Parry dress. Several would-be designs from the tour saw Parry riffing off this same love for bold prints and bodycon, sweetheart silhouettes.
With conversations continuing to buzz around what the performance (and fashion) will look like in the upcoming Winehouse biopic, one can only hope that they can properly capture the star’s beautiful, one-of-a-kind spirit. Her distinctive personal style has only continued to influence fashion designers—remember Jean Paul Gaultier’s 2012 couture tribute to her?—and even in 2022, her rock and roll fashion attitude clearly still lives on and is not any less thrilling to behold. She was in a league entirely of her own.
Below, more of Winehouse’s best fashion moments.