Fame10 Fashion Evolution: Lindsay Lohan

Published on May 2, 2014. Updated April 4, 2017

Remember back when Lindsay Lohan was one of the most fashionable young stars in Hollywood? It seems that numerous DUIs and jail stints aren’t good for the fashion sense. Not only is Lindsay no longer an in-demand actress, she can’t seem to pull it together on the red carpet anymore either.

Let’s take a look at the troubled starlet’s fashion evolution…

Premiere of Freaky Friday – 2003

Lindsay Lohan looked fresh-faced and innocent in this gold and black lacy dress at the premiere of “Freaky Friday.”  Even though she was only 16-years-old at the time, it wouldn’t be long before we saw this young, rosy-cheeked starlet everywhere.

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Teen Choice Awards – 2004

The “Freaky Friday” star dressed casually for the Teen Choice Awards where she secured her title as “teen queen.” She also took home four awards including best movie actress in a comedy and best big-screen hissy fit for her part in “Mean Girls.”

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Premiere of Herbie: Fully Loaded – 2005

Lindsay Lohan looked stunning at the premiere of “Herbie: Fully Loaded.” She shined in this watermelon-colored Valentino country dress with white polka dots.  It was the perfect mix of cute and chic! We don’t think Lindsay has ever looked better – she looked every bit the movie star!

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Premiere of Mr & Mrs Smith – 2005

With help from her stylist Rachel Zoe, the “Parent Trap” star was well on her way to becoming a full-on style icon! Lindsay wore this fitted Gucci dress with Chloe heels and a Tods Scala Pochette clutch with so much confidence that it was hard to believe that she was only 19-years-old at the time!

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Cartier Declare Your Love Day VIP Cocktail Reception – 2006

For the Cartier Declare Your Love Day VIP Cocktail Reception, Lindsay Lohan donned this black and white Hervé Léger halter dress. Even though the dress totally flattered the young starlet’s trim figure, Lindsay wasn’t the picture of health, appearing tired and wan.

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Prairie Home Companion Premiere – 2006

The A list star lit up the red carpet at the premiere of  “A Prairie Home Companion” in this one-of-a-kind Donna Karan gown.  In 2006, it appeared that young Lohan had the world at her fingertips. She was beautiful, talented, and she owned the red carpet with sass and style.

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MET Gala – 2007

Never one to miss an event, Lindsay Lohan attended the MET gala wearing a silk tuille gown by Zac Posen with custom-made Bally satin heels. Even though she looked divine, you’ll notice that the young starlet wasn’t looking as vibrant in these photos. This was coincidentally around the same time that Lindsay’s legal problems began.

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Chanel Cruise Show Presented by Karl Lagerfeld – 2007

The “I Know Who Killed Me” star looked rocker chic at the Chanel Cruise Show. She wore a sheer black minidress with a sequined bodice and a pair of star earrings. And she capped off the edgy look with silver-lined finger-less gloves and a black-and-white striped cuff bracelet.

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Clive Davis’ Annual Pre-Grammy Party – 2008

Lindsay Lohan wore this flirty, flowing turquoise one-shouldered bubble dress with gold peep toes to Clive Davis’ Annual Pre-Grammy Party. Even though the silhouette of the frock was flattering, the color of the dress was all-wrong on Lindsay, and the bright gold shoes were a bad, garish choice. It seemed, at this point, Lindsay’s  fashion sense was starting to slip…

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MTV Movie Awards – 2008

Lindsay Lohan showed up at the 2008 MTV Movie Awards wearing this short purple bandeau dress with a black belt by Dolce & Gabbana. However, the dress was a wee bit short for Lohan– a gust of wind end up blowing up the skirt while she was on the red carpet as all of the photographers snapped pictures of her underwear!

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Fashion’s Night Out – 2009

The “Herbie: Fully Loaded” star sported a boho look when she attended the Fashion’s Night Out celebration in New York wearing this vibrant blue Ungaro Spring 2009 shirt. She paired the ensemble with black leggings, a black top, sexy heeled boots, and a matching hat.

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MTV Movie Awards – 2010

The troubled starlet did not appear on top of her game at the 2010 MTV Movie Awards. She arrived wearing a sparkly Pamella Roland jumpsuit, which secretly covered her SCRAM alcohol-monitoring bracelet. Her face also looked surprisingly swollen, as did her lips.

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“Saints Row: The Third” Video Game Launch – 2011

Lindsay Lohan arrived at the “Saints Row: The Third” Video Game Launch looking rather disheveled in short black-sleeved dress with gold heels. Her face and lips both appeared rather swollen and her teeth looked like they were decaying. The former A list star has never looked worse.

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Weinstein Company’s 2012 Golden Globe After Party – 2012

After a series of fashion flops, “The Canyons” star put her best foot forward at the Weinstein Company’s 2012 Golden Globe After Party. She wore a nude Prada gown with Hermes bangles, Chopard jewels and a YSL clutch. We were surprised at the improvement since Lindsay hadn’t looked this well put together in years!

s_bukley / Shutterstock.com

“Mr. Pink” Energy Drink Launch – 2012

Lindsay Lohan showed up at “Mr. Pink” Energy Drink Launch in this sequined mini dress, which flaunted a little too much cleavage. We don’t think the dress looked super flattering on the struggling actress. What happened to her impeccable fashion sense from 2005 and 2006?

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