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Lindsay Lohan is a star who has practically lived her entire life in the spotlight, which means her style evolution has touched every corner of the sartorial spectrum.
From the wholesome, girl-next-door charm that launched her career as a child star in the Disney film The Parent Trap to the rebellious, boundary-pushing looks that defined her early 2000s rise, Lohan’s fashion journey has been vast. More than anything, however, her wardrobe choices have always reflected the era she was in.
Her decades-long career has seen many changes, and thus, so has Lohan’s style. As she steps back into the spotlight to star in Freakier Friday (the long-awaited sequel to the 2003 film Freaky Friday with Jamie Lee Curtis), it is clear her wardrobe has shifted from teen pop icon staples and edgy party girl ensembles to refined, contemporary looks.
This press tour run has seen Lohan wear everything from sophisticated floral dresses courtesy of Oscar de la Renta, to custom looks from Ludovic de Saint Sernin that nod to her film past. If you want a dose of nostalgia and clothing inspiration, look no further than the actor’s recent wardrobe choices.
Below, we revisit some of Lindsay Lohan’s most iconic style moments through the years—from her early aughts cool-girl attire to her glamorous gowns and getups worn across the world and at high-profile fashion events.
August 5, 2025
For the Australian premiere of Freakier Friday, Lohan slipped into a transparent LBD by Saint Laurent. She paired the low-key outfit with a gold metallic clutch and minimal jewelry.
July 31, 2025
While attending the Freakier Friday United Kingdom premiere at the Odeon Luxe Leicester Square theater in London, Lohan wore a custom Ludovic de Saint Sernin dress that was a reimagining of the look she wears for the final scene of 2003’s Freaky Friday.
July 28, 2025
Anyone else having major flashbacks to her Parent Trap days? Lohan wore a yellow-and-black tweed outfit, paired with a lemon-yellow headband and matching shoes, to make an appearance on Good Morning America.
July 28, 2025
Carrie Bradshaw would be proud. Lohan slipped into a fitted white Jacquemus midi dress equipped with a tulle tutu bottom (paying homage to Bradshaw) for a New York City screening of Freakier Friday. She even wore Jimmy Choo’s archive Leo sandals.
April 3, 2025
If there is one thing Lohan appreciates, it’s a good little black dress. Her gown with a sweetheart neckline was styled with a diamond necklace to receive the CinemaCon Vanguard Award.
March 2, 2025
Classic and elegant, Lohan looked so dreamy in a sleek white dress with a small train while attending the 2025 Vanity Fair Oscars after-party.
November 18, 2024
Lohan’s style can be described as timeless but with an edge. The black transparent gown with dramatic gold hardware that she wore to the screening of Our Little Secret is the perfect example of just that.
September 30, 2024
Lohan went full-on Matrix at the Balenciaga Spring/Summer 2025 womenswear show in Paris.
September 10, 2024
A cool-toned monochrome number looked so chic on Lohan as she exited the Michael Kors spring/summer fashion show in 2024.
September 09, 2024
A more elevated take on her go-to black dress style, Lohan opted for a lace, scalloped-hem Balenciaga dress at the Kering Foundation dinner.
March 10, 2024
A shimmering gown is always a fun choice. Lohan slipped into a metallic, strapless piece dripping with silver sequins for the 2024 Vanity Fair Oscars after-party.
March 5, 2024
Ice princess vibes. Lohan embodied class in a white slip dress with a ruched front and an ivory coat at an Irish Wish New York City screening.
February 9, 2023
There is nothing like a good monochrome moment, and in this case, Lohan made her red strands part of her look. Her copper ensemble at the Christian Siriano Fall/Winter 2023 New York Fashion Week show glowed with a rusty, metallic sheen.
January 16, 2008
Long before she was a mom, Lohan was a certified It-girl in Hollywood. Her slinky LBD at the Los Angeles premiere of Cloverfield, alongside her blonde locks, was her uniform during the early aughts.
September 5, 2006
While her style has undergone many different looks, so has her hair. Lohan’s raven hair perfectly contrasted against her white gown with silver gems along the neckline on the 2006 Cannes Film Festival.
May 9, 2006
Lohan made waves when she attended the Just My Luck Los Angeles premiere wearing a white halter dress with silver studs.
May 3, 2006
While at a parade for A Prairie Home Companion in St. Paul, Minnesota, Lohan opted for a sweet strapless beige gown with pink florettes down the center and a pale-yellow cardigan.
December 15, 2005
A dinner party look does not need to be complicated—Lohan knows this best. Her attire at an event for Rumor Has It was composed of a sequin midi gown and black pointed-toe pumps.
August 9, 2005
Lest you ever forget that Lohan is a style icon. Her dark denim and polka-dot scalloped top paired with a chunky belt was peak Y2K at the Four Brothers premiere in New York City.
June 14, 2004
In a white strapless minidress, Lohan looked every bit as sweet as her character at a Mean Girls London screening held at Charlotte Street Hotel.
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