The teen star wore a teal-colored velvet sweatsuit set for the The Neil Bogart Memorial Fund annual Tour for a Cure concert at Hollywood's Universal Amphitheatre on Nov. 4, 2002.
Lohan wore eggplant tones for the premiere of The Santa Clause 2 at Hollywood's El Capitan Theatre on Oct. 26, 2002.
The actress showed off her new bangs at the MTV Video Music Awards in New York City on Aug. 28, 2003.
Lohan rocked this midriff-baring sheer black blouse at the Teen Choice Awards at Universal Amphitheatre in Universal City, Calif., on Aug. 2, 2003.
Lohan wore a rainbow-colored crochet mini-dress for Mercedes-Benz Fall 2004 Fashion Week at Smashbox Studios in Culver City, Calif., on March 29, 2004.
The actress channeled her inner-Marilyn Monroe in this classic get-up for the Mean Girls premiere in New York on April 23, 2004.
Lohan paired her fuschia dress with bright heels and makeup at her Speak album release party in New York on Dec. 7, 2004.
Lohan revealed her new brunette locks at the VH1 Big in '05 Awards in Culver City, Calif., on Dec. 3, 2005.
The actress was a vision in cheetah print at the 2005 MTV Video Music Awards in Miami on Aug. 28, 2005.
Lohan looked elegant in white at the Cartier Celebrates 25 Years in Beverly Hills event in Los Angeles on May 9, 2005.
The actress matched the Casino Royale World Premiere Party's regal theme with a white fur coat in London on Nov. 14, 2006.
Lohan sported head-to-toe Chanel at the 2007/2008 Chanel Cruise Show in Santa Monica, Calif., on May 18, 2007.
Lohan looked stunning in a mesh-paneled abstract dress at the Fendi Rodeo Drive Flagship Store's "Ten Baguettes for Ten Years" Exhibition Auction in Los Angeles on Feb. 13, 2008.
The actress paired her crimped hair with an all-black outfit for The Cinema Society and Dolce and Gabbana screening of "Filth and Wisdom" at Landmark Sunshine Theater in New York City on Oct. 13, 2008.
Lohan sported a glam rocker-chic look at F1 Rocks Singapore concert in Singapore on Sept. 26, 2009.
Lohan looked Studio 54-ready in this disco-inspired hooded dress at the InStyle and Warner Bros. 67th Annual Golden Globes After Party in Los Angeles on Jan. 17, 2010.
Lohan wore a ruffled black-and-white dress for the Turkish Vogue Edition Launch Party in Paris on March 7, 2010.
The actress sparkled in a sequined jumpsuit (and new platinum tresses) at the MTV Movie Awards in Universal City, Calif., on June 6, 2010.
Lohan wore a '60s-inspired peach gown for HBO's Official After Party for the 69th annual Golden Globe Awards in Los Angeles on Jan. 15, 2012.
The actress hopped on the statement T-shirt trend, which sat just above her latex thigh-highs, for Z100's Jingle Ball 2013 at New York City's Madison Square Garden ion Dec. 13, 2013.
Lohan wore a sparkly zebra-patterned gown for the GQ Men of the Year awards at The Royal Opera House in London on Sept. 2, 2014.
Lohan's natural auburn hair was a pretty contrast to her sequined emerald mini-dress for the Gabrielle's Gala in London on May 7, 2014.
Lohan mixed fur, sheer details and an exposed bra at The World's First Fabulous Fund Fair in London on Feb. 24, 2015.
Lohan looked graceful in a cream-colored gown for the Butterfly Ball in London on June 22, 2016.
The actress was all smiles in a spring-chic ruffled dress for the de Grisogono "Love on the Rocks" party during the 70th annual Cannes Film Festival in Cap d'Antibes, France, on May 23, 2017.
Lohan beamed in a sophisticated black-and-white gown at the amfAR Gala Cannes in Cap d'Antibes, France, on May 25, 2017.
Lohan looked ready for the disco in this metallic layered mini-dress for the MTV EMAs in Bilbao, Spain, on Nov. 4, 2018.
The actress matched her fiery-red lipstick to her structured dress for "Watch What Happens Live With Andy Cohen" in New York City on Jan. 19, 2019.
Lohan kept things neutral in a feminine and feathery frock at the Melbourne Cup Day in Melbourne, Australia on Nov. 05, 2019.