Amy Winehouse: Inside the Music Legend’s Fashion Legacy

It’s been nearly 14 years since the world lost Amy Winehouse, the jazz, soul, and R&B legend whose distinctive style and vocals left an indelible mark on both music and fashion. While some of us may be too young to have experienced the Amy Winehouse era at its fullest, we are definitely old enough to appreciate and memorialize the enduring presence of the singer’s noteworthy style in contemporary fashion.

Winehouse’s blend of 1950s pin-up glamour with edgy and post-punk modernity not only set her apart during her time, but it continues to inspire designers and fashion enthusiasts alike. Her signature beehive hairstyle, bold winged eyeliner, and retro outfits resonate with younger generations who rediscover her, cementing her status as a timeless style icon.

Amy Winehouse’s style can be defined as more than just fashion, it was a contradiction in motion. Drawing inspiration from vintage wear but never bound by it, her look captured a spirit that expertly integrated elements of nostalgia while still remaining provocatively modern. Central to her image was the essence of rockabilly, a style from the 1950s derived from the popularity of early rock ‘n’ roll and working-class Americana. Winehouse reimagined the pin-up curls, polka dots, and pencil skirts through a grungier lens. She was also inspired by Betsey Johsnon’s playful, retro designs, incorporating similar pieces into her personal style.

Nevertheless, Amy reinvented the rockabilly style for the 21st century, making it entirely her own and taking the fashion world by storm in the process. While she clearly paid homage to mid-century aesthetics, her take was uniquely individualistic—an original spin that boldly diverged from the dominant fashion trends of the 2000s. In an era defined by low-rise jeans and mini skirts, her retro silhouette stood out as a striking and refreshing contrast. It quickly became an instantly recognizable staple of her personal brand and an essential part of her appeal (Novato, 2023). Her look offered a refreshing alternative and infused 50s rockabilly with a renewed sense of vigor. Unlike the more modest sensibilities of that era, Amy wasn’t afraid to show skin; she frequently performed and appeared in curve-hugging bodycon dresses, deep necklines, visible lace bras, sky-high pumps that amplified both her femininity and defiance.

“She would always add the Amy edge, the imperfection of the look that ultimately was the ingredient that made her unique.”

Her longtime stylist and close friend Naomi Parry (2021) says in her book, Amy Winehouse: Beyond Black, “Of course, no matter what I put her in, Amy was very much the architect of her ultimate appearance. It didn’t matter how armed I was with the correct underwear, tit tape, sewing kit, safety pins, etc; she would always add the Amy edge, the imperfection of the look that ultimately was the ingredient that made her unique.” That word, “imperfection,” was everything. Even in full glam, there was always something undone—a smudge of liner, a fallen curl, a strap slipping out of place. Amy’s style felt real, emotional, and lived-in. There was beauty in the imperfection. For Amy and Naomi, fashion wasn’t just about looking good: it was about storytelling, it was frankness, it was candor. Her style mirrored her music: vintage yet visceral. That’s exactly why it continues to resonate. Like her lyrics, Amy’s look wasn’t curated to please. It was built to be remembered.

In 2021, the Design Museum in London hosted Amy: Beyond the Stage, an exhibition that offered an intimate look into the life and legacy of the singer. Among the displays were handwritten lyrics, home videos, and studio memorabilia. There were curated selections from her personal wardrobe, including her iconic red heart-shaped Moschino bag worn at the 2007 BRIT Awards (Allaire, 2022). The exhibit contextualized her clothing as part of her storytelling. It presented her clothing as visual extensions of her artistry, identity, and vulnerability.

Other garments have also appeared in fashion retrospectives, including the GRAMMY Museum in Los Angeles and the Jewish Museum in London, where a 2013 show titled Amy Winehouse: A Family Portrait displayed some of her most recognizable outfits. These pieces, forever preserved behind glass, speak to the visual language she created. One that was deeply personal and culturally resonant.

Fourteen years after her tragic passing, Amy Winehouse’s style continues to hold cultural weight, not just for its visual impact but for what it represented. In an industry often defined by ultra-manufactured trends and image control, her fashion style was unapologetically personal. Amy wore what she liked, regardless of whether it was considered appropriate or in style. That resistance to conformity, paired with her reverence for vintage aesthetics, made her stand out at the time and ensured her influence remained relevant years on.

Today, as conversations around fashion center around authenticity and individuality, Amy’s wardrobe feels less like a relic of the past and more like a blueprint. Artists, fans, and designers continue to look to her not just for inspiration but for reassurance that being imperfect is just as important as being expressive.

Writer's Instagram: @marlombana

Article Sources

Allaire, Christian. “Amy Winehouse Will Forever Be the Queen of Retro Rockabilly Style.” Vogue, 14 July 2022, https://www.vogue.com/slideshow/amy-winehouse-best-fashion-moments. Accessed 9 April 2025.

Novato, Olivia. “Inside the Fashion Legacy of Amy Winehouse.” CR Fashion Book, 23 August 2023, https://crfashionbook.com/inside-the-fashion-legacy-of-amy-winehouse/.

Parry, Naomi. Amy Winehouse: Beyond Black. Abrams, 2021.

Photo Sources

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