The Lindsay Lohan Look Book
Photo: David Aguilera/BuzzFoto/FilmMagic
Lindsay Lohan first appeared on red carpets as a fresh-scrubbed, apple-cheeked 11-year-old starring in The Parent Trap. In those days, she dressed like most normal tweens did in the early aughts — think lots of Juicy Couture track suits, flared jeans, and babydoll dresses — her strawberry-blonde hair streaked with the occasional highlight. But as her star rose post–Mean Girls, she tackled edgier looks, swathing her newly adult figure in low-cut necklines and dying her hair a vampy deep auburn. When the tabloids began taking note of her activities, her fashion choices became even more pointed: She almost single-handedly started the trend of wearing leggings and slouchy tees in 2006, which she later incorporated into her own leggings brand, 6126, in 2008. It was around the same time that she began struggling with alcohol and drugs, which resulted in multiple trips to rehab; despite the negative attention, she remained hungry for the limelight, showing up to events in tight miniskirts and cleavage-baring tops, her hair color vacillating between bleach blonde and deep brown. Despite her checkered history and questionable employability, she remains one of the most carefully watched figures in pop culture today and continues to dress the part. Enjoy this look back through her most notable fashion moments, from the late nineties to the present.
June 22, 2016 Where: At the Butterfly Ball in London. Photo: Danny Martindale/WireImage
June 9, 2016 Where: London.
Photo: WeirPhotos / Splash News
September 22, 2015 Where: At Wonderland Magazine's 10th Anniversary Party in London. Photo: Keith Hewitt/GC Images
June 24, 2015 Where: At the i-D 35 x Jeremy Scott for Moschino party celebrating i-D Magazine's 35th anniversary in London.
Photo: David M...
June 24, 2015 Where: At the i-D 35 x Jeremy Scott for Moschino party celebrating i-D Magazine's 35th anniversary in London.
Photo: David M. Benett/Getty Images
June 10, 2015 Where: At the Louis Vuitton party in London.
Photo: Hewitt/JJ/GC Images
April 24, 2015 Where: In London. Photo: Gotcha Images / Splash News
March 20, 2015 Where: At Dstrkt Night Club in London. Photo: Keith Hewitt/GC Images
February 24, 2015 Where: At The World's First Fabulous Fund Fair in aid of The Naked Heart Foundation in London. Photo: Stuart C. Wilson /Getty ...
February 24, 2015 Where: At The World's First Fabulous Fund Fair in aid of The Naked Heart Foundation in London. Photo: Stuart C. Wilson /Getty Images
February 21, 2015 Where: At the Gareth Pugh show during London Fashion Week Fall/Winter 2015/16. Photo: Mike Marsland/Getty Images
February 3, 2015 Where: Leaving Jimmy Kimmel Live in Los Angeles. Photo: RB/Bauer-Griffin
December 9, 2014 Where: At the Sunday Times Style Xmas Party in London, England. Photo: David M. Benett/Getty Images
December 2, 2014 Where: At the Chopard Christmas Party at Annabel's member's club in London, England. Photo: 2014 Keith Hewitt
September 2, 2014 Where: At the GQ Men of the Year awards in London. Photo: 2014 Getty Images
July 1, 2014 Where: At Newark International Airport.
What: Sweater by Zoe Karssen. Photo: Alo Ceballos/2014 Alo Ceballos
June 16, 2014 Where: At the Moschino show during the London Collections: Men SS15. Photo: Tim P. Whitby/2014 Getty Images
June 2, 2014 Where: Walking in London. Photo: Keith Hewitt/2014 GC Images
May 7, 2014 Where: At Gabrielle's Gala in London, England. Photo: Mike Marsland/WireImage
April 7, 2014 Where: Arriving at The Late Show with David Letterman.
What: Dress by Ashish, booties by Christian Louboutin. Photo: Patricia Sch...
April 7, 2014 Where: Arriving at The Late Show with David Letterman.
What: Dress by Ashish, booties by Christian Louboutin. Photo: Patricia Schlein/Star Max/GC Images
January 6, 2014 Where: At the Sohu Fashion Achievement Awards in Shanghai, China. Photo: ChinaFotoPress/Getty Images
December 16, 2013 Where: In SoHo, New York City. Photo: 2013 Alo Ceballos
December 13, 2013 Where: At Z100's Jingle Ball in New York City. Photo: 2013 Kevin Mazur
September 19, 2013 Where: Walking in SoHo, New York City. Photo: 2013 Alo Ceballos
April 11, 2013 Where: At the the Scary Movie V Los Angeles premiere. Photo: 2013 Steve Granitz
April 9, 2013 Where: Walking in New York City. Photo: 2013 Star Max
March 19, 2013 Where: At the Santa Monica Police Station. Photo: Handout/2013 Santa Monica Police Department
March 18, 2013 Where: Leaving a courthouse in Los Angeles, California. Photo: Valerie Macon/2013 Getty Images
February 6, 2013 Where: Outside the amfAR Gala in New York City. Photo: Mike Coppola/2013 Getty Images
November 20, 2012 Where: At the premiere of Liz & Dick in Los Angeles.
What: Dress by Donna Dashini; shoes by Nando Muzi. Photo: Photograph...
November 20, 2012 Where: At the premiere of Liz & Dick in Los Angeles.
What: Dress by Donna Dashini; shoes by Nando Muzi. Photo: Photographer: Brian Dowling/© Corbis. All Rights Reserved.
October 11, 2012 Where: At Mr. Pink Ginseng Drink Launch Party in Beverly Hills, California. Photo: Valerie Macon/2012 Getty Images
May 9, 2012 Where: At the A+E Network's Upfront event in New York City. Photo: Dimitrios Kambouris/2012 Getty Images
April 28, 2012 Where: At the White House Correspondents' Association Dinner.
Photo: Paul Morigi/WireImage
April 24, 2012 Where: At Star Magazine's "All Hollywood" Event.
Photo: Imeh Akpanudosen/Getty Image
April 15, 2012 Where: At the Coachella Music Festival.
Photo: Christopher Polk/Getty Images
March 29, 2012 Where: Walking outside of her probation status hearing.
Photo: Jean Baptiste Lacroix/WireImage
February 22, 2012 Where: Walking outside of her probation status hearing.
Photo: Toby Canham/Getty Images
February 22, 2012 Where: At Domingo Zapata's Oscar Art Show presented by Mr. C Beverly Hills.
Photo: Frederick M. Brown/Getty Images
February 11, 2012 Where: Walking in New York City. Photo: Christopher Peterson/BuzzFoto/FilmMagic
February 8, 2012 Where: At the amfAR New York Gala to Kick Off Mercedes Benz Fashion Week.
Photo: Jemal Countess/Getty Images
January 15, 2012 Where: At the Weinstein Company Golden Globes after-party.
Photo: Jordan Strauss/WireImage
January 11, 2012 Where: At the Weinstein Company and Audi Celebrate Awards Season.
Photo: John Shearer/Getty Images for Audi
December 14, 2011 Where: Walking outside of her probation status hearing.
Photo: Toby Canham/Getty Image
November 2, 2011 Where: Walking outside of her Probation Status Hearing.
Photo: Toby Canham/Getty Images
September 24, 2011 Where: Walking with Philipp Plein during Milan Fashion Week. Photo: Photo by Tullio M. Puglia/Getty Images for Philipp Plein
September 23, 2011 Where: At amfAR MILANO. Photo: Vittorio Zunino Celotto/Getty Images for amfAR
September 9, 2011 Where: With Cynthia Rowley at the Cynthia Rowley spring 2012 runway show.
Photo: Duffy-Marie Arnoult/Contributo...
September 9, 2011 Where: With Cynthia Rowley at the Cynthia Rowley spring 2012 runway show.
Photo: Duffy-Marie Arnoult/Contributor/WireImage
July 21, 2011 Where: Walking outside of her progress report hearing.
June 23, 2011 Where: Walking outside of her probation status hearing.
Photo: Kevork Djansezian/Getty Images
May 7, 2011 Where: At Tyler Shields Presents "Life Is Not a Fairytale."
Photo: Stefanie Keenan/WireImage
April 22, 2011 Where: Walking outside of her preliminary hearing.
Photo: Toby Canham/Getty Images
April 5, 2011 Where: Walking in New York City. Photo: James Devaney/FilmMagic
February 23, 2011 Where: Walking outside of her preliminary hearing.
Photo: Jean Baptiste Lacroix/WireImage
February 9, 2011 Where: Walking outside of her preliminary hearing.
Photo: Jae C. Hong/AP/Corbis
February 4, 2011 Where: At the Giuseppe Zanotti Design Beverly Hills store opening.
Photo: John Sciulli/Getty Images for Giuseppe Zanotti Design
March 10, 2011 Where: Walking outside of her preliminary hearing.
Photo: Toby Canham/Getty Images
September 24, 2010 Where: Walking outside of her probation status hearing.
Photo: Toby Canham/Getty Images
September 14, 2010 Where: Walking outside of Santa Monica Courthouse.
Photo: Jean Baptiste Lacroix/Contributor/WireImage
September 3, 2010 Where: Shopping at the Grove in Los Angeles, California.
Photo: Jean Baptiste Lacroix/WireImage
July 20, 2010 Where: At her probation status hearing.
Photo: Toby Canham/Getty Images
July 20, 2010 Where: At the Los Angeles County Sheriff's Department.
Photo: Los Angeles County Sheriff’s Department via Getty Images
July 6, 2010 Where: Walking outside of her probation status hearing.
Photo: Michael Buckner/Getty Images
July 6, 2010 Where: At her probation status hearing.
Photo: David McNew/Getty Images
June 13, 2010 Where: In Hollywood, California.
Photo: Jean Baptiste Lacroix/Contributor/WireImage
June 6, 2010 Where: At the MTV Movie Awards.
Photo: Jason Merritt/Getty Images
May 24, 2010 Where: Walking outside of her probation status hearing.
Photo: Toby Canham/Getty Images
May 17, 2010 Where: At the Chopard 150th Anniversary Party at the Cannes Film Festival.
Photo: Pascal Le Segretain/Getty Images
May 17, 2010 Where: Arriving at a press conference in Cannes, France.
Photo: Vittorio Zunino Celotto/WireImage
March 22, 2010 Where: At the Adidas and Snoop Dogg More Malice Deluxe Album and Mini Movie Celebration.
Photo: Charley Gallay/WireImage
March 9, 2010 Where: With Karl Lagerfeld at the Chanel fall 2010 runway show in Paris, France.
Photo: Dominique Charriau/WireImage
March 7, 2010 Where: At the Turkish Vogue Edition Launch Party in Paris, France.
Photo: Julien Hekimian/WireImage
March 6, 2010 Where: At the Viktor & Rolf fall 2010 runway show.
Photo: Julien M. Hekimian/Getty Images
March 5, 2010 Where: With John Galliano at the Christian Dior fall 2010 runway show.
Photo: Eric Ryan/Getty Images
February 26, 2010 Where: At Milan Fashion Week. Photo: Tullio M. Puglia/Getty Images
February 16, 2010 Where: At the Brit Awards.
Photo: Fred Duval/FilmMagic
January 17, 2010 Where: At the Warner Bros. and InStyle Golden Globes after-party.
Photo: Kevork Djansezian/Getty Images
January 16, 2010 Where: At the Art of Elysium "Heaven" Gala Event.
Photo: Jason Merritt/Getty Image
October 31, 2009 Where: At the Grand Opening of Kerzner Mazagan Beach Resort in Morocco. Photo: Gareth Cattermole/Getty Images
October 19, 2009 Where: With Donatella Versace at the Whitney Museum Gala in New York City.
Photo: Dimitrios Kambouris/WireImage
October 4, 2009 Where: With Estrella Archs walking in the Emmanuel Ungaro spring 2010 runway show in Paris, France.
Photo: Pasca...
October 4, 2009 Where: With Estrella Archs walking in the Emmanuel Ungaro spring 2010 runway show in Paris, France.
Photo: Pascal Le Segretain/Getty Images
September 25, 2009 Where: At the F1 Rocks Singapore Concert.
Photo: Jun Sato/WireImage
September 7, 2009 Where: Walking in New York City. Photo: Justin Campbell/BuzzFoto/FilmMagic
September 5, 2009 Where: Walking to the Roxy in Bevery Hills, California.
Photo: David Aguilera/BuzzFoto/FilmMagic
August 17, 2009 Where: At the screening of Inglourious Basterds.
Photo: Andrew H. Walker/Getty Images for The Weinstein Company
June 27, 2009 Where: At her 23rd birthday party in Las Vegas, Nevada.
Photo: Ethan Miller/Getty Images for Wet Republic
April 22, 2009 Where: At the Us Weekly Hot Hollywood event.
Photo: Jeff Kravitz/FilmMagic
April 15, 2009 Where: At the launch of A/X Watches.
Photo: Michael Buckner/Getty Images
February 15, 2009 Where: At the Matthew Williamson New York Store Opening. Photo: Rabbani And Solimene Photography/WireImage
February 5, 2009 Where: At the Jenni Kayne and Andy Lecompte Salon Party in West Hollywood, California.
Photo: Jeff Vespa/WireImage
December 13, 2008 Where: With Samantha Ronson in Miami International Airport.
Photo: Miguel Garcia/WireImage
November 14, 2008 Where: With Samantha Ronson at VIP Room Theatre in Paris, France.
Photo: Julien Hekimian/WireImage
November 14, 2008 Where: At Lindsay Lohan's "6126" Launch. Photo: Andrew H. Walker/Getty Images
September 7, 2008 Where: At the MTV Video Music Awards.
Photo: Steve Granitz/WireImage
September 7, 2008 Where: At the MTV Video Music Awards.
Photo: Kevin Mazur/WireImag
September 6, 2008 Where: At the Charlotte Ronson spring 2009 runway show in New York City.
Photo: Stephen Lovekin/Getty Images for IMG
July 28, 2008 Where: With Samantha Ronson walking in New York City. Photo: James Devaney/WireImage
July 17, 2008 Where: At the Sephora Celebrates Ten Years of Gorgeous event.
Photo: Jamie McCarthy/WireImage
June 1, 2008 Where: At the MTV Movie Awards.
Photo: Jeffrey Mayer/WireImage
May 23, 2008 Where: At the Dolce and Gabbana Party at the Cannes Film Festival.
Photo: Stefano Meluni/LaPresse/dpa/Corbis
April 28, 2008 Where: At the LG Electronics' Launch of the Scarlet series.
Photo: Jordan Strauss/WireImag
April 19, 2008 Where: At "Samantha Ronson Spins at Hawaiian Tropic Zone," in New York City.
Photo: Astrid Stawiarz/Getty Images
March 14, 2008 Where: At the Scandinavian Style Mansion.
Photo: Jordan Strauss/WireImage
February 13, 2008 Where: At the Fendi Store Opening in Beverly Hills, California.
Photo: Donato Sardella/WireImage
February 9, 2008 Where: At the Clive Davis Pre-Grammy Party.
Photo: Vince Bucci/Getty Images
January 16, 2008 Where: At the premiere of Cloverfield.
Photo: Michael Buckner/Getty Images
December 5,2007 Where: At a commerical shoot in Los Angeles, California. Photo: Todd Williamson/WireImage
November 15, 2007 Where: At the Los Angeles County Sheriff's Department.
Photo: Los Angeles County Sheriff’s Department via Getty...
November 15, 2007 Where: At the Los Angeles County Sheriff's Department.
Photo: Los Angeles County Sheriff’s Department via Getty Images
July 2, 2007 Where: At her 21st birthday party. Photo: Kevin Mazur/WireImage
May 18, 2007 Where: With Karl Lagerfeld at the Chanel Cruise Show.
Photo: Mark Mainz/Getty Images for Chanel
May 16, 2007 Where: At the Maxim Hot 100 Party.
Photo: Evan Agostini/Getty Images
May 8, 2007 Where: At the Georgia Rule premiere in New York City.
Photo: Jamie McCarthy/WireImage
May 7, 2007 Where: At the MET Costume Institute Benefit Gala Presents "Poiret: King of Fashion."
Photo: Peter Kramer/Getty Images
May 5, 2007 Where: In New York City. Photo: James Devaney/WireImage
April 28, 2007 Where: At the Coachella Valley Music and Arts Festival.
Photo: Michael Tran/FilmMagic
April 26, 2007 Where: At the Us Weekly Magazine Hot Hollywood Party.
Photo: Stephen Shugerman/Getty Images
April 13, 2007 Where: With Samantha Ronson at a Charlotte Ronson event in Tokyo, Japan.
Photo: Junko Kimura/Getty Images for Showroom Seven
January 11, 2007 Where: At the "Chanel And Sienna Miller Host an Intimate Dinner."
Photo: Frazer Harrison/Getty Images for Chanel
November 29, 2006 Where: At the GQ Man of the Year Awards.
Photo: Lester Cohen/WireImage for GQ Magazine
November 17, 2006 Where: At the Donna Karan Gold Fragrance Launch.
Photo: Nick Harvey/WireImage
November 1, 2006 Where: At the AFI FEST presented by Audi opening night gala of Bobby.
Photo: Vince Bucci/Getty Images for Audi
November 2006 Where: With Elijah Wood in Bobby.
October 25, 2006 Where: At the "Gucci by Gucci" Book Party With Film Foundation.
Photo: Donato Sardella/WireImage for Guccio Gucci Spa
October 18, 2006 Where: At the Tommy Hilfiger Paris Store Opening Cocktail. Photo: Tony Barson/WireImage
September 5, 2006 Where: At the Venice Film Festival.
Photo: Franco Origlia/Getty Images
June 27, 2006 Where: At the Benefit the Charlize Africa Outreach Program event. Photo: Eric Charbonneau/WireImage
June 15, 2006 Where: In New York City. Photo: RJ Capak/WireImage
June 9, 2006 Where: Shopping in New York City. Photo: Mel Bouzad/FilmMagic
June 8, 2006 Where: At Cartier and Interview Magazine Celebrate Love.
Photo: Peter Kramer/Getty Images
June 5, 2006 Where: With Karl Lagerfeld at the CFDA Fashion Awards. Photo: Evan Agostini/Getty Images for CFDA
June 4, 2006 Where: At the A Prairie Home Companion premiere.
Photo: Evan Agostini/Getty Images
June 2, 2006 Where: With Karl Lagerfeld at the Dom Perignon Rose Party in Los Angeles, California.
Photo: Stephane Cardinale/Peop...
June 2, 2006 Where: With Karl Lagerfeld at the Dom Perignon Rose Party in Los Angeles, California.
Photo: Stephane Cardinale/People Avenue/Corbis
May 23, 2006 Where: At the GQ / Calvin Klein Celebrity Poker Tournament Benefiting Peace Games.
Photo: Donato Sardella/WireImage
May 9, 2006 Where: At the premiere of Just My Luck. Photo: Michael Buckner/Getty Images
May 1, 2006 Where: At the MET Presents "Anglomania: The Costume Institute Benefit Gala."
Photo: Peter Kramer/Getty Imag...
May 1, 2006 Where: At the MET Presents "Anglomania: The Costume Institute Benefit Gala."
Photo: Peter Kramer/Getty Images
April 18, 2006 Where: At the Condé Nast Traveler Hot List Party.
Photo: Bryan Bedder/Getty Images
April 18, 2006 Where: At the Prada celebrates the opening of the "Waist Down: Skirts by Miuccia Prada" exhibition after-party.
Photo:...
April 18, 2006 Where: At the Prada celebrates the opening of the "Waist Down: Skirts by Miuccia Prada" exhibition after-party.
Photo: RJ Capak/WireImage
April 18, 2006 Where: At the Prada celebrates the opening of the "Waist Down: Skirts by Miuccia Prada" exhibition.
Photo: Jamie McCart...
April 18, 2006 Where: At the Prada celebrates the opening of the "Waist Down: Skirts by Miuccia Prada" exhibition.
Photo: Jamie McCarthy/WireImage
April 1, 2006 Where: At the Kid's Choice Awards.
Photo: Frazer Harrison/Getty Images
March 31, 2006 Where: With Samantha Ronson at the Diesel Presents Young Hollywood Awards Countdown.
Photo: Lester Cohen/WireImage...
March 31, 2006 Where: With Samantha Ronson at the Diesel Presents Young Hollywood Awards Countdown.
Photo: Lester Cohen/WireImage for Diesel
March 9, 2006 Where: At the Cinema Society & Piaget host the premiere of Ask the Dust in New York City.
Photo: Evan Agostini/Getty I...
March 9, 2006 Where: At the Cinema Society & Piaget host the premiere of Ask the Dust in New York City.
Photo: Evan Agostini/Getty Images
March 5, 2006 Where: At the Vanity Fair Oscar party.
Photo: Mark Mainz/Getty Images
February 28, 2006 Where: At the General Motors Ten Celebrity Fashion Show in Los Angeles, California.
Photo: Steve Granitz/WireImage
February 12, 2006 Where: With Meryl Streep at the A Prairie Home Companion photocall and press conference in Berlin, Germany.
Pho...
February 12, 2006 Where: With Meryl Streep at the A Prairie Home Companion photocall and press conference in Berlin, Germany.
Photo: Sean Gallup/Getty Images
February 6, 2006 Where: With Ali and Dakota Lohan at Child Magazine's fall 2006 runway show.
Photo: Bryan Bedder/Getty Images for...
February 6, 2006 Where: With Ali and Dakota Lohan at Child Magazine's fall 2006 runway show.
Photo: Bryan Bedder/Getty Images for Child Magazine
February 3, 2006 Where: Walking in the Heart Truth Red Dress runway show.
Photo: Arun Nevader/FilmMagic
December 31, 2005 Where: Walking in Miami, Florida. Photo: Uri Schanker/Getty Images
December 3, 2005 Where: At the VH1 Big in '05 event.
Photo: KMazur/WireImage
December 1, 2005 Where: At the GQ Men of the Year Celebration.
Photo: David Livingston/Getty Images
November 22, 2005 Where: At the American Music Awards.
Photo: Vince Bucci/Getty Images
November 16, 2005 Where: At the Gucci Fashion Show Benefitting the Childrens Action Network.
Photo: Mark Mainz/Getty Images
November 11, 2005 Where: With Ali Lohan at MTV's TRL.
Photo: Peter Kramer/Getty Images
October 22, 2005 Where: At the CFDA/Vogue fashion show sponsored by Cartier in Los Angeles, California.
Photo: Donato Sardella/WireImage for Vog...
October 22, 2005 Where: At the CFDA/Vogue fashion show sponsored by Cartier in Los Angeles, California.
Photo: Donato Sardella/WireImage for Vogue and Vogue.com