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The freckle-faced 12-year-old celebrated her first movie role at the Hollywood premiere of Disney?s The Parent Trap in July 1998.
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In October 1999, Lohan mingled with stars like Alec Baldwin at the Carol M. Baldwin Breast Cancer Research Fund Benefit in New York City.
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She may have been dressed down in jeans and a T-shirt, but Lohan looked all grown up when she attended the premiere of Treasure Planet in 2002.
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The actress promoted the body-swapping comedy Freaky Friday ? and showed a little skin ? at the 2003 Teen Choice Awards.
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Lohan celebrated her 17th birthday with father Michael and mom Dina at a party hosted by LEGO Clikits in 2003.
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In February 2004, Kelly Osbourne and her brother Jack (not pictured) accompanied the 17-year-old actress to the 46th annual Grammy Awards in Los Angeles.
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In 2004, Lohan scored her first invite to the Vanity Fair Oscar party, where she posed for photographers with Mischa Barton.
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The former Disney star crossed paths with Nickelodeon phenom Amanda Bynes on the orange carpet at the 2004 Kids' Choice Awards.
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In April 2004, the actress celebrated the premiere of Mean Girls with Tina Fey, and landed on People?s 50 Most Beautiful list.
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Already a red carpet veteran, Lohan posed with relative newcomer Anne Hathaway at the Fundraiser for Defense for Children International in May 2004.
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Lohan, Whitney Houston and Bobby Brown were among the guests at a disco-themed bash to celebrate the launch of Christian Dior?s D'Trick collection in 2004.
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Before kicking off her gig as host of the 2004 MTV Movie Awards, Lohan greeted 7th Heaven star Jessica Biel on the red carpet.
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In September 2004, Lohan cozied up to boyfriend Wilmer Valderrama at the 5th annual Latin Grammy Awards.
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A newly blonde Lohan and her new pal Nicole Richie partied for a cause at the 12th annual Race to Erase MS fundraiser in April 2005.
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In May 2005, the actress raised eyebrows when she showed off her noticeably thinner physique at the Cartier 25th anniversary party in Beverly Hills. ''There's a lot of pressure [to be thin],'' the actress told Access Hollywood later that month.
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At a preview of auction items from the estate of Marilyn Monroe in June 2005, Lohan channeled her idol in a flirty strapless frock by designer Michael Kors.
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After stopping for a photo op with Sandra Bullock, the Mean Girls star (wearing a Chanel dress) picked up the 2005 MTV Movie Award for best female performance.
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Wearing a boho dress from Valentino and Cartier diamonds, Lohan reunited with co-stars Michael Keaton, Matt Dillon, and Justin Long at the Hollywood premiere of Herbie: Fully Loaded in June 2005.
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Lohan, her Prairie Home Companion co-star, Meryl Streep, and Angelina Jolie were visions in white at a Yele Haiti Haitian relief benefit in August 2005.
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In September 2005, Lohan joined in on a fashionable fete hosted by Dior for Proof star Gwyneth Paltrow.
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Lohan and Ginnifer Goodwin were among the fashion It girls invited to a special presentation of the Gucci Spring 2006 fashion show in November 2005.
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The actress-slash-singer brought little sister Ali along when she attended Teen People's 4th annual Artists of the Year party in Los Angeles in November 2005.
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At GQ?s 2005 Men of the Year bash in December 2005, Lohan turned heads in a little black dress and a diamond engagement ring reportedly given to her by Chapter 27 co-star Jared Leto.
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Lohan took side boob to a new extreme at a General Motors celebrity fashion show in February 2006.
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Salma Hayek admired Lohan's Louis Vuitton ensemble at the Cinema Society & Piaget screening of Ask The Dust in March 2006.
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Lohan went back to her redheaded roots for the premiere of 2006?s Just My Luck, where she joked around with co-star Chris Pine.
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In June 2006, designer Karl Lagerfeld dressed Lohan for — and escorted her to — the 2006 CFDA Fashion Awards in New York City.
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In August 2006, Lohan dressed casual for the Entertainment Weekly pre-Emmy party in Los Angeles.
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Lohan (in a floor-length Marchesa gown) re-teamed with Christian Slater, Emilio Estevez, Freddy Rodriguez, and Svetlana Metkina for the premiere of Bobby at the 2006 Venice Film Festival.
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After becoming fast friends in the fall of 2006, Lohan and Rumer Willis — wearing carefully coordinated outfits — kissed for photographers at the 21st Annual American Cinematheque Award ceremony in Beverly Hills.
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Lohan had gone blonde again, when she (and her hair extensions) turned up for Us Weekly?s Hot Hollywood party in Los Angeles in April 2007.
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Despite reports that she?d caused plenty of drama on the set, Lohan (in Jill Stuart) and co-stars Jane Fonda and Felicity Huffman presented a united front at the premiere of Georgia Rule in May 2007.
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After a stint in rehab, Lohan (dressed in a skin-tight bandage dress from Herve Leger) made a memorable return to the red carpet at the Los Angeles premiere of Cloverfield in January 2008.
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After partying with Diddy aboard his yacht, Lohan slipped into a super-short Dolce & Gabbana mini-dress to attend the fashion label?s Cannes Film Festival bash in May 2008.
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In November 2008, Lohan celebrated the launch of the holiday collection from her 6126 legging line with a party at PURE Nightclub in Las Vegas.
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Lohan, her girlfriend Samantha Ronson, and Ronson?s mother, Ann Dexter-Jones, were among the jet setters that traveled to the United Arab Emirates for the grand opening of Atlantis in Dubai.
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In the summer of 2009, Lohan hyped her Sevin Nyne brand self-tanning mist with an appearance at the Wet Republic pool at the MGM Grand in Las Vegas.
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The blonde-again-off-again star used her platinum tresses to avoid a wardrobe malfunction at the Cinema Society & Hugo Boss screening of Inglourious Basterds in August 2009.
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At the InStyle and Warner Bros. 2010 Golden Globes after party, Lohan tried to keep a low profile in a hooded dress by designer Brian Lichtenberg.
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In March 2010, Lohan made the rounds of Fashion Week festivities in Paris, arriving at the VIP Room wearing a sparkly dress and a leopard-print coat, and looking a little worse for wear.
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The sparkly Pamella Roland jumpsuit Lohan wore to the 2010 MTV Movie Awards may not have been a fashion home run, but at least it was functional — the star's wide-leg suit hid her SCRAM alcohol-monitoring bracelet.
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Lohan had somehow morphed into Victoria Gotti's doppelganger when she posed with the mob princess at a press conference for Gotti: Three Generations in April 2011.
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Clad in an Alexander Wang LBD, Lohan helped the Weinstein Company celebrate awards season during a party at L.A.?s Chateau Marmont in January 2012.
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Lohan turnedheads in a white Tom Ford dress at the 2012 amfAR New York gala to kick offFall 2012 Fashion Week in New York City.
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At the 2012 White House Correspondents' Dinner in Washington, DC, Lohan proved she could still make quite an entrance.
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The actress tried — and failed — to channel old Hollywood glamour in a silk Donna Dashini gown and fur stole at the Lifetime premiere of Liz & Dick in November 2012.
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At the April2013 premiere of Scary Movie V, Lohan (in Dolce & Gabbana) braved the press line with a little help from pal Charlie Sheen.
More from EW
Ring in 2017 With These TV Countdown Parties