20 Years Later, Amy Winehouse’s Unmistakable Personal Style Still Feels Ahead of Its Time

Jason Sargent Wednesday, October 28, 2026

Kristen BatemanTue, October 27, 2026 at 5:26 PM UTC

Amy Winehouse Redefined Pop Star StyleDaniel Boczarski - Getty Images

With her swoop of jet-black beehive hair, sharp-as-a-knife cat-eye eyeliner, and skinny jeans, Amy Winehouse defied the neat, overly curated pop star style of the early aughts. Rather than looking like everyone else, she was a purely individualistic amalgamation of vintage and her own curated, undone personal style pulled from the aesthetic of her local Camden in London as well as her favorite style stars like her grandmother and Brigitte Bardot.

Twenty years after the release of her second and final album, Back to Black, it’s impossible to ignore the late singer’s influence on music and fashion. With a new exhibition in London showcasing her iconic looks, a massive tribute concert, Back to Black’s special 20th anniversary re-release, and 2008 fashion on the rise, Winehouse’s style is as important as ever.

Andy Willsher - Getty Images

She wore white tank tops, little denim shorts with black leather studded belts and tiny gingham dresses. Winehouse’s tattoos, visible black and red bra straps, and thick gold chains were as key to her look as her hair and makeup (the cat-eye eyeliner, which she proudly did herself). Beyond winning five Grammy Awards in one night, she defined a short but impactful era. “I don’t want to be the prettiest or the sexiest or whatever. I just want to look different and to look like me,” she told The Guardian in 2004. Early on, Amy Winehouse worked with the stylist Lou Wood for photo shoots. “One day she turned up in a massive pair of high heels and hot pants, carrying a guitar,” she recently told The Independent. “We were walking for five hours,” she says, laughing. “She wasn’t a manufactured artist. She had her own mind definitely, and her own style.” Winehouse also collaborated with her longtime friend Naomi Parry as a stylist.

Paul Bergen - Getty Images

Carlos Alvarez - Getty Images

Winehouse pulled from the retro style of 1950s and 1960s icons who wore pedal pushers, tight sweaters, and denim, and made it her own, piling on the accessories like belts from Topshop or jumbles of gold, real and fake, curated from a mix of places ranging from her grandmother to street markets. At the Brit Awards in 2007, she wore a bright lemon yellow minidress by Preen with a scarlet heart Moschino bag and cherry red hoop earrings with white polka dots. She often mixed prints like plaid with leopard print. She named Elizabeth Taylor, Miles Davis, and Busta Rhymes as her style icons. She even inspired Chanel’s pre-fall 2008 collection, with Karl Lagerfeld famously citing, “She’s beautiful and gifted. And I very much like her hairdo. Amy is the new Brigitte Bardot.”

But perhaps her most iconic style was her ballet flats, which she famously wore ’til they were blackened, torn, and shredded to the ground. She bought some of her signature pink satin ballet shoes in bulk from Freed of London, a dance shop near Covent Garden. They were frequently replaced by her stylist as they disintegrated from Winehouse’s concerts and running around. Even if she loved a sky-high heel, she could be seen changing into ballet flats midway through some of her shows.

It was never a costume and it was impossible to replicate. In an era of polished and overly curated fashion, Amy Winehouse made imperfection iconic.