It’s undeniable that British pop culture would be different if Lily Allen didn’t exist. Ever since she appeared on the radio in 2006 with her hit single “Smile”, she has cemented herself as a pillar of British music. Her clever social commentary wrapped up in breezy pop melodies have paved the way for today’s artists, from Charli xcx to PinkPantheress. Allen’s latest album, West End Girl, has received critical acclaim and internet praise for its scathing storytelling and biting lyrics.
And she is just as creative and daring with her fashion as with her music. Allen was one of the main proponents of indie sleaze fashion in the 2000s. She would wear prom dresses with trainers and Chanel bags on red carpets, just because she could. But now that she’s turned 40, Allen has embraced the more elegant side of fashion, often wearing classic, chic dresses that accentuate her silhouette. Being the rebel that she is, Allen also never shies away from pairing different colours, textures and fabrics together to create something uniquely her. Here are some of our favourite outfits from Lily Allen.
Lily Allen in a prom dress
September 9, 2006 performing onstage at Bestival in the Isle of Wight wearing a prom dress
Photo: Tabatha Fireman/Redferns
Allen was known for her eclectic wardrobe and punk approach to fashion: she only cared if she had fun in her clothes. And during the early years of her career, she really did. In 2006 at Bestival, a discontinued music festival on the Isle of Wight in the UK, she performed in a quintessential white prom dress featuring layers upon layers of tulle. But what did she choose to wear with the dress? Grey sneakers, a pink bob wig and bunny ears. Classic Allen.
Lily Allen in Vivienne Westwood
February 16, 2014 attends the EE British Academy Film Awards 2014 in London wearing Vivienne Westwood
Photo: Samir Hussein/WireImage
Music rebel meets fashion rebel. Lily Allen and Vivienne Westwood teamed up at the 2014 BAFTAs, and the results were surprisingly colourful and fun. Lily Allen wore a dress with a bright orange corset, a neon pink train, an oversized orange bow that wrapped around the waist and draped off her back, and a pink feather headpiece tucked behind her hairdo. This was a bold but fashionable step up for Allen, who was remembered by early fans for her prom-dress-and-sneakers stage looks.
Lily Allen in Fendi
November 29, 2021 attends The Fashion Awards 2021 in London wearing Fendi
Photo: Justin Goff Photos/Getty Images
While Allen can pull off the indie sleaze and the whimsical, she showed us that she can be just as sophisticated as well. At the 2021 Fashion Awards in London, Allen stepped out in a clean-cut Fendi ensemble. The outfit’s key piece was a backless silver satin waistcoat, which paired with matching wide-leg trousers, and a thin belt around her waist. Though we love the adventurous and playful fashion choices of her past, sometimes, less is more.
Lily Allen in Chanel
June 10, 2024 attends the Chanel Tribeca Festival Artists Dinner in New York
Photo: Sean Zanni/WireImage
Allen and Chanel go way back: She had a close relationship with Karl Lagerfeld, starring in the campaigns for Chanel’s Cocoon bags in 2009 and performing on his Spring/Summer 2010 runway. But her Chanel look for the Tribeca Festival Artists Dinner in 2024 was by far the most tasteful. Allen wore a yellow embroidered vest with a strawberry pattern, paired with a maxi skirt in pastel pink and blue stripes. The ensemble was super feminine, but the red tips in Allen’s hair gave it her signature edge.
Lily Allen in Anna Fleischle
April 3, 2026 at the Chicago stop of her West End Girl tour wearing Anna Fleischle
Photo: Emma McIntyre/Getty Images for Live Nation
Right now, Allen is embarking on a world tour to promote her latest album, West End Girl. The tour fashion has spread like wildfire on the internet, thanks to Anna Fleischle, the production and costume designer of the tour. The most head-turning look of them all is Allen’s own revenge dress, or should I say, receipt dress? The dress features receipts of things her ex-husband, David Harbour, allegedly bought for other women. The receipts are held up for the crowd to see, and span the entire length of the stage. Allen has always had a sharp tongue in her music, but this proves she’s not afraid to speak her truth in her fashion as well.
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Matt ChauCredit
Photo: @lilyallen via Instagram
