Amy Winehouse Will Forever Be the Queen of Retro Rockabilly Style

This week, it was announced that a new Amy Winehouse biopic is in the works from Fifty Shades of Grey director Sam Taylor-Johnson. The film will aim to document the late English singer’s spectacular rise and fall, and Twitter was instantly abuzz with speculations around which actor will portray the iconic singer-songwriter (a current fan-favorite? Lady Gaga). It’s an impossible role to fill: Winehouse’s unique musical sound—blending elements of jazz, soul, rhythm, and blues—and one-of-a-kind look, complete with her signature beehive and retro rockabilly dresses, is a challenge to replicate on-screen. In honor of the news, Vogue is taking a look back on the late singer’s inimitable wardrobe.

Since making a splash with her debut album, Frank, in 2003, Winehouse never strayed from being authentically herself. She had a consistent love for both retro sounds and style. For performance outfits, she frequently borrowed from the 1950s (although she added her own grunge to them). Rockabilly style emerged in the South during the decade, when rock music began taking over the airwaves; Women began wearing shapely halter dresses—often in polkadot prints—and high-waisted pencil skirts, also tying their beehive hairdos up with a bandana. It’s a look that Winehouse began really adapting when she released her second album, Back to Black, in 2006—an influential record that would skyrocket her to global stardom, thanks to her hits such as “Rehab,” “Back to Black,” and “You Know I’m No Good.”

Photo: Getty Images

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.