Amy Winehouse's life in looks: her 42 most memorable outfits from Koko Camden to Glastonbury
Talk of Amy Winehouse has taken over London once more, following the premiere of Sam Taylor-Johnson’s biopic Back to Black — a glossy flick which sees actor Marisa Abela slip into late, great singer’s Fred Perry polos and ballet pumps.
Winehouse’s shoe of choice is a TikTok magnet and runway trend today — but there should be no mistaking the Tears Dry On Their Own singer was as original in her music as she was anti-fashion in her look. Reeboks, skinny jeans and a pea coat served her better at Brits after parties than stilettos, and any “style evolution” largely involved a graduation from knee length, body-hugging midi dresses to the pouf-skirt minis and slapping-great leather belt which went on to became her stage signature. That, and the beehive, which she first created with hairstylist Tracey Cahoon in 2000.
By way of a fashion stylist, Winehouse began working with her friend Naomi Parry following the 2006 release of the Back to Black album. According to Parry, Amy “always had a clear idea about how she wanted to look. She said, “we found a style that she was really comfortable with, and it became synonymous with her. It was like her armour — she put that on and became Amy Winehouse.”
Her most memorable outfits moved from Karen Millen black, rose-printed corset midi dresses and tropical cotton minis worn to perform at Koko in Camden and the Hammersmith Apollo in the mid noughties, through to the navy, floral appliqué Luella strapless mini (complete with cocktail umbrellas in hive) at Glastonbury in 2008. There was the yellow Preen ‘power’ dress — black, lacy bra on show — at the Brits 2007, a Dolce & Gabbana black cotton mini which she wore to win five Grammys in 2008, and a Vivienne Westwood ‘Anglomania’ skirt suit for a trip to Westminster Magistrates Court in the summer of 2009.
While she dabbled with designer brands — and they did her, notably Karl Lagerfeld who paid tribute to her for the Chanel Pre-Fall 2008 collection — her own uniform of vest tops, micro shorts, leather jackets and denim remained the most Winehouse. A pair of Miss Sixty jeans, on display at the Design Museum's 2021/2022 exhibition Amy: Beyond the Stage exhibition, perhaps sum up her style best: worn out, and customised with red embroidery to read ‘Amy’ on the leg, and across the back pocket: ‘Sinatra is God’.
Amy Winehouse’s 42 most memorable outfits:
At the Brit Awards, 2004
At The Prince's Trust Urban Music Festival, 2004
At a MAC party, 2004
At an event celebrating the life and music of Billie Holiday, 2004
At the Ivor Novello Awards, 2004
At a Blackberry party, 2004
At Cannizaro Park Festival in Wimbledon, 2004
At the Mercury Music Prize awards, 2004
At the Q Awards, 2004
At the Brit Awards, 2005
Performing at Koko in Camden Town, 2006
At the Q Awards, 2006
At the South Bank Show Awards, 2007
At the Elle Magazine Style Awards, 2007
At the Brit Awards, 2007
Performing at the Brit Awards, 2007
At the Universal / Island Records Brits after party, 2007
At Coachella Music Festival with Kelly Osbourne, 2007
Performing at Shepherd's Bush Empire, 2007
At the MTV Movie Awards in California, 2007
Performing at the MTV Movie Awards in California, 2007
Performing at the Isle of Wight Festival, 2007
At the MOJO Honours List awards with Blake Fielder-Civil, 2007
Performing on the Pyramid Stage at Glastonbury, 2007
Performing at Lollapalooza in Chicago, 2007
At the launch dinner of The Row with Mary Kate and Ashley Olsen, 2007
Performing at the Mercury Music Awards, 2007
Performing at the Music of Black Origin Awards (MOBOs), 2007
At the MTV Europe Music Awards in Munich, 2007
At the Grammy Awards ceremony in London, 2008
Performing at the Brit Awards, 2008
At the 46664 Concert In Celebration Of Nelson Mandela's Life, 2008
Performing on the Pyramid stage at Glastonbury, 2008
Performing at the Rock in Rio festival in Spain, 2008
Performing at a club night in Camden, 2008
Performing at T In The Park Festival, 2008
At Sadie Frost's closing party for her show 'Touched for the very first time', 2009
At Westminster Magistrates Court with her father Mitch Winehouse, 2009
At Westminster Magistrates Court, 2009
At Universal Music’s Lucian Grainge’s VIP Party, 2010
At the Reebok and VICEstyle.com launch party, 2010
At the after show party for Tony Bennett's concert at Royal Albert Hall, 2010
