Today, artistry extends far beyond musicianship. As they ascend the charts, artists are armed with tightly curated teams, spanning makeup artists, stylists and photographers. Together, they construct a manicured image for adoring fans to lap up - it takes a village, after all.
To throw another cliché into the mix, Rome wasn’t built in a day - and neither was Lily Allen’s wardrobe. Since bursting onto the Noughties music scene with her 2006 hit Smile, the British singer has held space in the imagination of millennials across the country.
Feisty, outspoken and peppy, the BRIT Award winner gained widespread recognition for her raw lyrics and upbeat tunes. Her clothing choices only bolstered her success, with colourful prom dresses becoming something of a signature in the early days.
© GettyLily’s wardrobe matured with her, with brands such as Chanel and Fendi knocking on her door. Appearances at The Fashion Awards and the Chanel Tribeca Festival Artists Dinner became an annual event in her calendar, leading to an evergreen carousel of statement looks.
Following the release of her album, West End Girl, on October 24, which detailed the breakdown of her marriage with actor David Harbour, all eyes have been on Lily. Read on to unearth her most iconic outfits from across the years.
Lily Allen’s most iconic fashion moments:
© Getty ImagesCFDA Fashion Awards 2025
Lily looked to Colleen Allen's spring/summer 2026 collection for her CFDAs 2025 look. Her co-ord featured a cream silk bralette adorned with delicate lace-trimmed embroidery, while the barely-there top was styled with a floor-length, ivory silk skirt that boasted a sheer lace panel.
© WireImageChanel Tribeca Festival Artists Dinner
Aptly wearing head-to-toe Chanel, the singer attended the Chanel Tribeca Festival Artists Dinner back in 2024. She opted for a mismatched co-ord featuring a strawberry-dotted top and pastel pink longline skirt with striped detailing.
© WireImageBRIT Awards 2014
Lily looked zesty with a lime-tipped updo as she graced the red carpet at the The BRIT Awards 2014. A floor-skimming, sequinned navy gown with a fluted tail and a raised neckline made for a disco-inspired after-hours look.
© FilmMagicMet Gala 2022
Once again sporting Chanel with a flick of fringe, Lily stepped onto those oh-so famous steps in New York to attend the 2022 Met Gala celebrating the theme 'In America: An Anthology of Fashion.'
© Getty ImagesBRIT Awards 2007
A classic Lily Allen look, the star hit the floor at the 2007 BRIT Awards in a prom-style frock complete with a strapless design, a ruched waistband and a vibrant teal satin construction.
© FilmMagicFashion Awards 2021
A backless, silver-blue jumpsuit by Fendi was the musician's choice of ensemble for the Fashion Awards 2021. A belted waistband and cut-out panels made for striking additional detailing.
© WireImageThe Serpentine Gallery Summer Party 2025
The Serpentine Gallery Summer Party 2025 saw the songwriter serve up monochrome magic in 16Arlington. She slipped into a strapless black gown with whimsical feathered detailing and a sculpting silhouette. A large polka dot print peppered the skirt of the garment.
© Dave Benett/Getty ImagesCharles Finch & Chanel Pre-BAFTA Party
A beaming Lily arrived at the Charles Finch & Chanel Pre-BAFTA Party back in 2020 sporting one of her most colourful looks to date. She slipped into a lime green and sky blue lace gown with a ruffled caped effect, topped off with a quilted, velvet Chanel bag.
© Getty Images2025 Planned Parenthood Gala
Channeling her inner Ariel, Lily attended the 2025 Planned Parenthood New York Gala sporting a glimmering sea green skirt paired with a cropped gold top. She housed her evening essentials in a cookie-topped bag by Puppets & Puppets.
