Lily Allen burst onto the music scene in 2006, with hits including “Smile”, “LDN” and “Knock ‘Em Out” – but it wasn’t just her music that drew attention.
Pairing ballgowns with trainers and flat caps with eyeliner, Allen created a look that set her apart from other pop stars.
Now, as she prepares to turn 40 this May, the singer is taking a more refined approach to fashion, whilst also dipping her toe back into the archives.
Speaking to Vogue in 2024, Allen reflected on her evolving fashion sense, noting a renewed confidence in her appearance.
“Today, Brooklyn Mom me is feeling pretty again for the first time in a long while,” she said.
Fashion’s 20-year rule seems to be true, as the original Lily look of a pretty dress and sneakers is trending once again this season, this time with drop waist dresses and ‘sneakerina’ trainers.
“As I approach 40,” Allen said, “I find myself revisiting it again too.”
Here’s a look back at her fashion evolution throughout the years:
2006
After a year of uploading demos to the social media network MySpace, Allen debuted her album Alright, Still in July 2006. It was an immediate hit, with the singer performing at V Festival that August.
Allen wore an extravagant strapless pastel ball gown, with silver chain necklaces and an optic white trucker cap.
It was this performance that cemented Allen’s personal brand of vintage dress and trainers – a style philosophy that carries on to this day.
2007
Allen’s love of loud dresses was immortalised in a collection with the high street retailer, New Look, in 2007.
The collaboration, called Lily Loves, featured spaghetti straps, frills and vintage-inspired prints, evocative of the ensembles the singer sported on stage.
Of course, Allen didn’t forget footwear, and featured retro Converse-style sneakers, with Eighties geometric shapes emblazoned on the canvas.
The year 2007 was also when Allen first performed at Glastonbury Festival, hitting the right notes in her trademark trainer-and-prom dress look.
Allen wore a Fifties-style fuchsia strapless gown, with matching pink lipstick and a pair of white and pink Nike Air Jordans.
2008
In 2008, Allen began to experiment with her trademark look – from shoes to dresses to hair dye.
Her red carpet appearances and stage performances featured a new cult classic for the singer: peep-toe Christian Louboutin heels.
At the Cannes Film Festival, Allen wore a sheer black Chanel dress, which marked the beginning of a long-term love affair with the brand.
In the summer, Allen had dyed her hair bubble gum pink and started to opt for more relaxed silhouettes on stage.
The star frequented three-quarter-length jeans, relaxed tanks and elevated accessories, such as her Chanel earrings she wore at the O2 Wireless festival.
Meanwhile, Allen’s off-duty looks leaned into the smart casual-clubbing trend of the decade, featuring peplums, pencil skirts and sheer tights.
2009 and 2010
In 2009, Allen once again performed at Glastonbury, following the release of her second album, It’s Not Me, It’s You, which featured now classics such as “The Fear” and “Not Fair”.
This time, Allen stepped out in a plunging periwinkle jumpsuit with a ruffled neckline and purple wig.
Off stage, Allen sported the boho-meets-rock ‘n’ roll aesthetic – donned by the likes of Kate Moss and Sienna Miller – in a chiffon and sequin jacket layered over a vest and black jeans.
It was from here on out that Allen began to sport more grungy and gothic apparel, wearing a black, torn knitted dress and sparkling tights to T in the Park.
Come the end of the decade, Allen actively showed her loyalty to Chanel, stepping out on several red carpets wearing the label.
Allen wore a Chanel cream and silver sequinned drop-waist dress with a Peter Pan collar to the 2009 Q Awards in October, showcasing a more relaxed side-swept shag cut of her classic fringe.
In February 2010, Allen wore a Chanel gothic metallic black gown with a red and gold neckpiece to the BRIT Awards.
The star styled the look with a black and burgundy smoky eye and her trademark black bangs.
2011
Allen married her first husband, builder and decorator Sam Cooper, in 2011 at St. James Church in Cranham, Gloucestershire.
Allen wore a lace vintage-inspired cream gown by French designer Delphine Manivet.
The dress featured sheer sleeves, a fluted bottom and a 3ft train, paired with Rupert Sanderson shoes.
The singer later announced she was hiding a baby bump under the swathes of lace, which would be her eldest daughter, Ethel.
During this pregnancy, following a traumatic stillbirth of her son, George, in 2010, Allen kept a relatively low profile.
Her pregnancy wardrobe featured her old favourites – including floaty mini dresses, Fifties-style peacoats and peep-toe heels.
2014
By the mid-2010s, Allen’s style had taken a modern twist, following the release of her third album, Sheezus.
Allen stepped out in eclectic pieces – combining fun accessories and smart stilettos with vivid block colouring – more evocative of what her style is today.
She combined bright accessories with collared shirts, blending her playful taste with more mature design details.
2018
In 2018, following the release of her fourth album No Shame, Allen began using vivid colours more in her wardrobe – from fluorescent limes to potent purples.
She also experimented with shape and silhouette, opting more for streetwear over her previous shirts and dresses.
2020 – today
From the 2020s, Allen has pared back her style, sporting far more classic styles from polo necks to tweed trench coats.
In 2022, Allen wore a strapless black Givenchy dress with black floral appliqué to the Olivier Awards.
She paired the look with a matching Givenchy leather bag and diamante pointed pumps.
And just like in 2008, the star is still sporting her favourite French label Chanel, apparent in the monochromatic set she wore to the pre-Bafta party last year.