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Evening Standard
Evening Standard
Lifestyle
Joe Bromley

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

(Getty Images)

At The Prince's Trust Urban Music Festival, 2004

(Getty Images)

At a MAC party, 2004

(Dave Benett)

At an event celebrating the life and music of Billie Holiday, 2004

(Dave Benett)

At the Ivor Novello Awards, 2004

(Dave Benett)

At a Blackberry party, 2004

(Dave Benett)

At Cannizaro Park Festival in Wimbledon, 2004

(Getty Images)

At the Mercury Music Prize awards, 2004

(Getty Images)

At the Q Awards, 2004

(Getty Images)

At the Brit Awards, 2005

(Getty Images)

Performing at Koko in Camden Town, 2006

(Getty Images)

At the Q Awards, 2006

(Dave Benett)

At the South Bank Show Awards, 2007

(Dave Benett)

At the Elle Magazine Style Awards, 2007

(Dave Benett)

At the Brit Awards, 2007

(Getty Images)

Performing at the Brit Awards, 2007

(Getty Images)

At the Universal / Island Records Brits after party, 2007

(Dave Benett)

At Coachella Music Festival with Kelly Osbourne, 2007

(Getty Images)

Performing at Shepherd's Bush Empire, 2007

(Getty Images)

At the MTV Movie Awards in California, 2007

(Getty Images for MTV)

Performing at the MTV Movie Awards in California, 2007

(Getty Images)

Performing at the Isle of Wight Festival, 2007

(Getty Images)

At the MOJO Honours List awards with Blake Fielder-Civil, 2007

(Dave Benett)

Performing on the Pyramid Stage at Glastonbury, 2007

(Getty Images)

Performing at Lollapalooza in Chicago, 2007

(Getty Images)

At the launch dinner of The Row with Mary Kate and Ashley Olsen, 2007

(Dave Benett)

Performing at the Mercury Music Awards, 2007

(AFP via Getty Images)

Performing at the Music of Black Origin Awards (MOBOs), 2007

(Getty Images)

At the MTV Europe Music Awards in Munich, 2007

(Getty Images for MTV)

At the Grammy Awards ceremony in London, 2008

(Getty Images for NARAS)

Performing at the Brit Awards, 2008

(Getty Images)

At the 46664 Concert In Celebration Of Nelson Mandela's Life, 2008

(Dave Benett)

Performing on the Pyramid stage at Glastonbury, 2008

(Getty Images)

Performing at the Rock in Rio festival in Spain, 2008

(Getty Images)

Performing at a club night in Camden, 2008

(Dave Benett)

Performing at T In The Park Festival, 2008

(Getty Images)

At Sadie Frost's closing party for her show 'Touched for the very first time', 2009

(Dave Benett)

At Westminster Magistrates Court with her father Mitch Winehouse, 2009

(Getty Images)

At Westminster Magistrates Court, 2009

(AFP via Getty Images)

At Universal Music’s Lucian Grainge’s VIP Party, 2010

(Dave Benett)

At the Reebok and VICEstyle.com launch party, 2010

(Dave Benett)

At the after show party for Tony Bennett's concert at Royal Albert Hall, 2010

(Dave Benett)

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