Get in loser, we’re going through all of Lilo’s most iconic fashion moments.
We often don’t give Lindsay Lohan enough credit for her impact on fashion and culture across the last two decades. The starlet, who rose to fame in a myriad of Disney films, quickly became the name on everyone’s lips with her iconic acting performances (The Parent Trap, Freaky Friday, Mean Girls…), two studio albums, a never ending stream of paparazzi pics and her singular fashion sense that we all wanted to emulate. From the mini dresses, low-rise jeans and strappy heels of her Y2K era to the mid-noughties LA glam that caught the eye of The Bling Ring teens, Lindsay served up looks with a dose of her playful sense of humour. Even into the early 2010s she continued to define trends of the moment through fashion lines and enviable street style.
Now, the actress, model, singer, socialite, fashion designer, i-D cover star, Mykonos club owner, Masked Singer judge and viral dancing meme is back with her new festive Netflix movie, Falling For Christmas. It’s reportedly only the first of multiple projects the icon has in the works with the streamer, meaning the Lilo renaissance has well and truly begun.
While we expect there will be many more iconic fashion moments from the unstoppable star, we look back at some of her best outfits to chart her style evolution from the 90s to today.
At a movie screening in New York, 2001
We saw Lindsay wearing army pants and flip-flops, so we bought army pants and flip-flops. Before that iconic line had even been thought up by Mean Girls writer Tina Fey, our Lilo had already paraded this laid-back style at an HBO event in Southampton, New York. Wearing distressed patchwork khaki trousers with a navel-grazing fitted black vest, platform flip-flops, a chunky beaded choker and what looks like an Apple watch but is definitely not an Apple Watch, the look — alongside her Juicy Couture tracksuits — is emblematic of Lindsay’s Y2K style: cute and casual with a little bit of grunge.
At the Teen Choice Awards, 2003
With a slew of successful Disney films now under her belt, and the body-switching comedy Freaky Friday days away from release, Lindsay arrived at the Teen Choice Awards alongside her co-star Jamie Lee Curtis to present the Choice TV Comedy Actor award (to Ashton Kutcher for That 70’s Show). Lindsay’s look was fun and daring with a black bra under a sheer frilly cardi-top and the ultra low-rise jeans that would become integral to her signature style.
At the Mean Girls premiere, 2004
Lindsay has always had an affinity towards Marilyn Monroe, the late actress, singer and ‘bombshell’ model of the 50s who was likewise hounded by the press. At the premiere of Mean Girls — the film that took Lilo from child star to a 00s teen tour de force — the star wore her go-to: a mini-dress, in a breezy white style that had clear nods to her idol. Lindsay would continue to honour Marilyn throughout her career from ringleted hair on the covers of New York Magazine and Playboy, to whatever this bizarre comedy sketch is and reading excerpts from Marilyn’s diary for a 2012 documentary.
At a movie premiere in LA, 2005
A Lindsay Lohan vs Paris Hilton movie may be in the works
Around this time, Lindsay hired stylist to the stars Rachel Zoe who was the go-to fashion oracle for Nicole Richie, Paris Hilton and Mischa Barton, and pioneered the LA ‘boho-chic’ style. Tabloids and fans alike noticed that Lindsay’s style had stepped it up a notch, which was fitting for the major household name she had quickly become. Making an appearance at the premiere for the Brangelina spy film Mr & Mrs Smith, Lindsay showed off a sultry metallic Gucci gown and Chloe heels with her newly platinum beachy hair.
At a fundraiser with Nicole Richie and Tommy Hilfiger, 2006
Alongside Marilyn and the 50s, Lindsay style was also inspired the flapper girls of the Roaring Twenties. Arm in arm with designer Tommy Hilfiger and then BFF Nicole, before chatting the night away with other icons of the moment, Gossip Girl’s Michelle Trachtenberg and One Tree Hill’s Sophia Bush, Lindsay stunned in this animated crystal-white fringe mini-dress.
At the MTV VMAs, 2008
A recurring theme within the fashion history of Lindsay Lohan is the whimsy and silliness she loves to express in her sartorial choices. The press were of course going to talk about her anyway, so why not give them something to talk about! And where better to do so than the ever controversial MTV VMAs. Take this seemingly normal dress she wore to the 2008 ceremony — the year Britney won her first Moon Man and everyone was arguing about purity rings. The minimal House of Holland fitted garment featured fun open zip detailing across Lilo’s boobs and butt, cheekily visible when she turned around or moved her hair.
At Bloomingdale’s, 2009
a few of the most memorable celebrity fashion lines
In 2008 Lindsay released a collection of leggings under her new fashion line 6126, the name a reference to Marilyn’s birthday. From dramatic cut outs to excessively high waists, pockets and lace panelling, each design had fittingly Lohan-esque names like “fame”, “lust” and “star”. The leggings were a huge success, selling at retailers across the US including the Kardashian’s DASH store, and they eventually led to an expansive clothing collection in 2010. i-D’s Mahoro Seward even noted that “Lindsay made leggings so hot that between 2008 and 2013, an entire micro-generation of teenage girls literally only ever wore leggings and sweaters on trips to regional shopping centres the nation over.” The power that that has.
At the Liz and Dick movie premiere, 2012
Lindsay was cast to play another one of her bygone icons: silver screen starlet Elizabeth Taylor, in the 2012 Lifetime movie Liz and Dick. The film would follow the actress’ tempestuous relationship with Richard Burton. who she met on the set of Cleopatra. An avid fan, Lindsay had previously paid tribute to the star on the Karl Lagerfeld-shot cover of Interview magazine in 2006. At the premiere for the movie, the starlet served Old Hollywood glamour in a svelty Donna Dashini gown and chic stole.
At the Falling For Christmas premiere, 2022
The news that our queen was making her return to a lead role in a mainstream movie after 13 years sent us feral (the last was 2009’s Labor Pains). Lindsay arrived at the premiere in a floral-embroidered Valentino naked dress that was fittingly mesmerising for her glorious cinematic comeback. Falling For Christmas is a festive remake of the 1987 movie Overboard, with Lindsay playing a spoilt heiress with amnesia who is taken in by a local hottie (Glee’s Chord Overstreet) and learns to live like a normal person. The best thing about the movie though? For its soundtrack, Lindsay recorded a new version of the song “Jingle Bell Rock”, a song famed for the iconic choreography and slutty Santa looks of The Plastics in Mean Girls. Lindsay knows how to keep her stans fed.
