Everyone’s Favourite Mean Girl: Lindsay Lohan’s Style Evolution

Baby-faced and sporting an embroidered, pastel blue dress, baby LiLo was an undeniable cutie in her early red carpet days.

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There’s a Mean Girls joke here, and we’re gonna make it: “Lindsay Lohan wore army pants with flip flops – so we bought army pants with flip-flops”. Sorry, not sorry! FYI: army-everything was the style of the day, so from the start, it was clear Lindsay liked to keep up with the trends.

Sporting a velour tracksuit — and for some reason, accessorizing it with a crochet scarf — Lindsay Lohan stepped out in 2002 for a Britney Spears tribute event looking like a hot mess. We’re still trying to understand the flip-flops…

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The Freaky Friday star looks all grown-up at the 2003 Teen Choice Awards. In a sheer, belly-baring top and low-rise jeans, Lindsay Lohan makes it clear she’s no longer that baby-faced cutie from The Parent Trap.

2004 was a big year for LiLo, who released her debut album and had lead roles in two major motion pictures – with her role in Mean Girls working to cement her status as the Hollywood “it-girl” of the moment. On the romance front, Lindsay was dating That 70’s Show star Wilmer Valderrama, who she accompanied to the 2004 Latin Grammy Awards. For the occasion, Lindsay was all smiles in a floral slip dress and strappy heels.

Never forget, Valderrama was a celeb who was dating a teen — kind of gross and not OK.

Almost unrecognizable without her signature red locks, Lindsay Lohan spents the majority of 2005 playing with drastically different hair colours and fashion styles. Our favourte of this year would have to be her ultra-dark brunette phase, which had Lindsay rocking dramatic gowns, super-low cuts and bold beauty choices, like the red lip she wore to the AMA’s in 2005.

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A very blonde Lindsay Lohan turned heads in a fitted animal-print dress at the 2005 MTV Video Music Awards. Experimenting with her hair colour this year, LiLo seemed to have the most fun as a platinum blonde, matching her besties du-jour, Paris Hilton and Nicole Ritchie.

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2006 was a roller coaster year for Lindsay Lohan, whose film Just My Luck was panned by critics, while her performance in the dramatic film Bobby earned her praise and positive reviews. Dressed in a bright green, a-line mini dress, Lindsay stepped out for a photo call for Bobby looking the part of an indie-film star on the rise at the Venice Film Festival.

On the heels of her second DUI, box-office flops like I Know Who Killed Me, in which Lindsay Lohan played a stripper with a dual personality, it seemed LiLo’s career downturn in 2006 was spilling over into 2007. In spite of her personal and professional struggles, Lohan kept up with appearances, literally, as the actress continued to show face at every red carpet opportunity. For the Maxim Hot 100 party, Lohan sported a trendy bandage-style mini in a rainbow print and donned strawberry-blonde locks for the event.

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Lindsay Lohan is all about the legs, and she stuck to her love of flirty minis when she stepped out for the 2008 MTV Movie Awards. Whether Lohan was all smiles because she nailed this look — or over her budding romance with DJ Samantha Ronson — we may never know, but both her developing style and new romance seemed to represent an uptick in the troubled actress’ life.

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Newly single, her last debut album stalled indefinitely and coming off of a string of highly-criticized work projects, the era of LiLo seemed to be hitting a dead end. While the starlet looked healthy and happy in a low-cut sequin jumpsuit at the 2010 MTV Movie Awards, it seemed the actress had hit a major impasse in her Hollywood career.

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Looking bizarrely-blonde but otherwise chic on the red carpet of an amfAR event in 2012, Lindsay Lohan was beginning to make the Hollywood rounds as she laid out plans for a comeback. She would host Saturday Night Live for her 4th time as host to mixed reviews, star as Elizabeth Taylor in the TV film Liz & Dick, a role which she would garner her mostly negative press, and take on several television cameos, none of which would work to establish the comeback Lohan had probably been hoping for.

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Dabbling in new professional arenas, Lindsay Lohan premiered in her first stage performance in 2014. A lead in Speed the Plow, a role originally played by Madonna, Lohan received generally negative reviews. On the style front, the fashion chameleon continued to explore new styles in beauty and fashion, wearing an iridescent long-sleeve midi dress to an after party for Speed the Plow.

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Through personal and professional missteps, one thing that has remained consistent for Lindsay Lohan is her love of a red carpet. Dressed up in a floor-length black gown with a super-high slit and fishnet stockings, Lohan proves there’s always a little room in life for glam.

Lindsay Lohan has always had a fascination with vintage themes, in particular, anything to do with the Marilyn Monroe era, and this comes through in her choice of styling for a 2017 amfAR event. The hair, the pearls, the cut of the dress, it all feels very retro – and while the nod to throwback trends is sweet, the look is a miss on Lohan.

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No glitz, no feathered coat, no towering stilettos — it’s taken most of her years in the spotlight, but Lindsay Lohan finally nailed a “casual look” when she was spotted in New York in 2018. Wearing a monochromatic tan pantsuit with sneakers and oversized sunglasses, Lohan looks chic, understated and, in the best way possible, on-trend.

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Fashion can sometimes be a little harsh — and Lindsay Lohan’s look for St Laurent Spring/Summer 2019 was exactly that. With super pale skin, slicked-back hair, sharp angles and exaggerated proportions, this was definitely one for the couture books. Working this ensemble at a 2018 preview during Paris Fashion Week, Lohan proved she can adapt to the high-fashion and work it with the best of them. You go, LiLo.

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One thing you have to love about LiLo, she finds a party anywhere she goes — even if it’s just a party of one. Looking adorable in a white feather-detail mini dress with a full skirt, Lohan twirls up a storm at an event for Melbourne Cup Day and has us feeling some serious FOMO for missing out on quite possibly the best backdrop for the ‘gram ever.

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Having started to buy up nightclub venues in Greece in 2016, Lindsay Lohan signed on for a reality TV show with MTV that would follow her role as an owner of a new Mykonos beach club. The show would be cancelled after just one season.

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In a (surprise, surprise) sparkly mini dress, Lindsay Lohan was right at home on the red carpet while attending a gala in 2019. With promises of new music and film projects on the horizon for 2020, we’re hoping to see more of LiLo this year — but less of these outdated glitzy dresses.

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