(Content warning: This story mentions mental illness.)
Amy Winehouse has always stood apart from her high-charting counterparts in the music industry, not only for extraordinary talent, diverse musical influences, and relatable themes, but also for her authentic and deeply personal fashion sense. Amy turned heads in the fashion world with her unique style. Maxine Builder for Bustle Magazine points out that in 2007 (the year Winehouse won a Grammy for Record of the Year), “…Karl Lagerfeld cited Winehouse as an inspiration for Chanel’s collection, while Brooklyn Vegan hypothesized that ‘Amy Winehouse’ was the year’s most popular Halloween costume.”
Amy divided audiences with her unapologetic attitude, but one thing that even critics could agree on was that throughout her experimentation she was completely herself, acting as a trailblazer for female artists often pushed into boxes.
Pop music today is dominated by a variety of influential women, and a memorable style is critical to your persona as a musician. Developing a clear visual identity gives fans an idea to support the story of their music. Amy changed things for a lot of female musicians by normalizing confessional and publicly vulnerable storytelling. Amy, like many others, used fashion a form of rebellion against societal standards. Winehouse took stereotypically feminine aesthetics and juxtaposed them with her unfiltered and vulnerable storytelling discussing topics that, in the United Kingdom’s musical climate in the early 2000s were shied away from.
Her track “Mr. Magic (Through the Smoke)” along with many more focus on addiction, similarly to “I Heard Love Is Blind” and “You Know I’m No Good,’ discussing infidelity. This was notable during a time when the music industry was much more formulaic, and in turn, standards about general freedom of expression were much stricter. Amy was asked in a 2006 talk show appearance about whether her management agency—who had also worked with artists like the Spice Girls, widely criticized for their industry-fabricated image—had attempted to change her in any way.
Winehouse paid the question no mind, replying, “I’ve got my own style, and I wrote my own songs, and when someone has so much of something already, there’s very little you can add.” Her personal style, which drew inspiration from retro pin-up girls and rockabilly fashion, was just one aspect of what made Amy so memorable in the competitive pop landscape.
She leaned into traditional counterculture aesthetics with bright red lipstick, thick angled eyeliner, old-school tattoos, and a voluminous beehive inspired by soul musicians from the 1960s. During her early career, most of her fashion statements were laid back, but that’s not to say they were plain. Instead, the way she wore her clothes gave her a sense of effortlessness, as seen on the cover of her first album Frank, where she was photographed in her pajamas walking her dogs past the trash. Winehouse typically worried more about authenticity than about perfection.
Her fashion sense was always focused on maximizing drama and incorporating bold pieces with emotional imagery. Some examples of this are roses in her hair, delicate corsets, head scarves, heavy makeup, and long red nails. Amy enjoyed pushing visual boundaries, immortalized by her iconic black beehive hairstyle, shapely defined dresses, oversized hoop earrings, extra short miniskirts, and dynamic layering.
Winehouse uses her sensuality to point out the irony of a male-centered world, presenting herself as almost a caricature of “womanhood.” Amy wore lots of polka dots, gingham, and satin while sporting tall heels and pearl necklaces with her lacy lingerie deliberately peeking out from under her outfit. She made femininity and sensuality her own, taking historically feminine pieces like ballet flats and vintage dresses and contrasting them with her unapologetic, brash attitude.
Amy defies presumptions about what “femininity” means, refusing to let her self-expression be governed by societies’ expectations. Musically, her impact and genius in contemporary jazz is unparalleled, which is notable especially as an artist in a genre that had little mainstream representation for anything taboo at this point in time. Her persona allowed her to retain an image of grace and allure, even at her messiest, and her musical talent was profound enough to remain at the center of her work.
Her fashion sense during the hardest periods of her life was incredibly raw. During her public breakup with Blake Fielder-Civil, she often experimented with androgyny and utilitarian styles, donning polo shirts and skinny jeans. Similarly, she leaned into darker aesthetics when going through times of immense struggle, famously depicted in her music video for “Back To Black.” She wore her heart on her sleeves and used her clothing as a means of coping with her reality.
Amy’s lyrics were relatable and engaging to audiences in part because they were authentically tragic. The most vulnerable parts about her lifestyle unfortunately were at the foremost of her life in the public eye; she was often mischaracterized by tabloids to reinforce a narrative of irresponsibility and recklessness. Daily Mail published headlines reading “Back to beehive as Wino drinks until 4am” and the Mirror wrote “Amy Winehouse’s drunk face doesn’t surprise us anymore.”
Amy struggled with her self-esteem and mental health from a young age. She saw a psychiatrist who medicated her for her anxiety and alcohol disorder, yet she refused medication for her bipolar disorder which, left untreated, increases the likelihood of continuing her substance abuse. Amy had a history with severe bulimia that also went largely unacknowledged by herself and those close to her, making her still the more vulnerable. There are suspicions that beyond her parents’ traumatic separation, her father was also manipulative of Amy and her success into her final years. The media preyed on her self-destructive tendencies yet failed to support the artist or bring attention to the emotional abuse going on behind the scenes.
Amy’s impact is insurmountable. She opened doors for female musicians to exist as morally gray, emotionally complex, and open about their weaknesses. The impact of her unique sense of self is best put by Vogue writer Anja Stankovic: “She allowed women to be complicated in pop music without requiring them to explain their complexity in the end.” Similarly to her unique sense of style, her lyrics required no one else’s approval except her own. Today, we can take inspiration from Amy’s undying desire to express herself authentically while paying homage to the history of the artists that came before, both in her raw, soulful music and in her unique visual style.
If you or someone you know has an eating disorder and needs help, call the National Eating Disorders Association helpline at 1-800-931-2237, text 741741, or chat online with a Helpline volunteer here.
If you or someone you know is seeking help for mental health concerns, visit the National Alliance on Mental Illness (NAMI) website, or call 1-800-950-NAMI(6264). For confidential treatment referrals, visit the Substance Abuse and Mental Health Services Administration (SAMHSA) website, or call the National Helpline at 1-800-662-HELP(4357). In an emergency, contact the National Suicide Prevention Lifeline at 1-800-273-TALK(8255) or call 911.
If you or someone you know is seeking help for substance use, call the SAMHSA National Helpline at 1-800-662-HELP(4357).