Lindsay Lohan has been in the spotlight since she was 3 years old, which is when she first signed to Ford Models. Because of her early start, a majority of her devoted fanbase has had the rare opportunity to grow up with her. By the time she was 12, Lohan was cast in her first feature film: 1998’s The Parent Trap. Fast forward to 2003, when Lohan starred in Freaky Friday (alongside Jamie Lee Curtis, no less). While promoting the family-friendly comedy, the then-teenager solidified herself as a trendsetter, both on and off the red carpet. Since then, Lohan has experimented with countless aesthetics, including indie sleaze, Y2K, and old Hollywood glamour — all of which are still present in her red carpet circuit, thanks to the Lohanaissance (IYKYK).
As longtime Lohan fans know, her entire life has been incessantly documented by the tabloids — and in turn, so has her style evolution. After a decade of intense fame and public scrutiny, Lohan relocated to Dubai in 2014, where paparazzi are illegal. “I feel like some of [my work] got overshadowed by paparazzi and all that kind of stuff when I was younger, and that’s kind of annoying. I wish that part didn’t happen,” Lohan told Bustle in a 2024 interview. In November 2022, she returned to Hollywood around the release of Falling For Christmas — her first blockbuster in nearly 10 years. At the movie’s premiere, the actor walked her first red carpet since 2019 in a semi-sheer column dress from Valentino. Her lace-embellished number signaled the start of what fans dubbed the Lohanaissance: a new, mature era of elevated ensembles that spotlight a hint of sultriness.
In the years since her Hollywood homecoming, Lohan’s sartorial rebrand has only strengthened. Most recently, at the premiere of her latest holiday film, Our Little Secret, the 38-year-old (who recently welcomed her first child, son Luai Shammas) broke the internet in another see-through selection. Complete with a transparent maxi skirt, a plunging bodysuit, and ocean-inspired accents, Lohan chose a black gown from Zuhair Murad. This LBD immediately secured her a spot on numerous best-dressed lists.
All this to say? Lohan’s red carpet evolution is one of Hollywood’s most storied. Here, appreciate her best looks thus far, from childhood to motherhood.
The Parent Trap Premiere, 1998
At just 12 years old, Lohan arrived at her first red carpet soirée in style. The up-and-comer looked adorable in a periwinkle mini dress adorned with ivory pearlescent embroidery.
Dinner With Friends Screening, 2001
To support her The Parent Trap co-star, Dennis Quaid, in his new film, Lohan delivered major cool-girl outfit inspo in camouflage cargo pants, a black tank, and matching flip flops. Extra points for her beaded choker.
Freaky Friday Premiere, 2003
Before snapping a pic with her Freaky Friday co-star, Curtis, Lohan posed for a solo shot in a metallic gold mini dress topped with lacy trim and a black satin bow around her waist.
MTV Video Music Awards, 2003
In the early 2000s, Lohan was a frequent guest of the MTV Video Music Awards. One of her most memorable looks? Distressed flared jeans paired with a white button-down underneath a black corset. If you look closely enough, you’ll see she secured her bustier with suspenders — a staple accessory for millennials.
Mean Girls Premiere, 2004
At one of the many Mean Girls press events, all eyes were on Lohan in a flowy turquoise midi dress, metallic silver sandals, and a classic diamond tennis necklace.
MTV Video Music Awards, 2005
Marking her third MTV Video Music Awards in a row, Lohan brought her fashion A-game in an off-the-shoulder midi dress by Alexander McQueen. The luxe leopard pattern aligns perfectly with today’s animal print renaissance.
Vanity Fair Oscar Party, 2006
Lohan proved her sartorial prowess early on in her career — especially at the 2006 Vanity Fair Oscar Party. She was a vision in a champagne-colored satin gown embellished with sparkly rhinestones at the bodice.
Met Gala, 2006
Just 10 years into her career, Lohan secured an invitation to the Met Gala. She ascended the iconic staircase in a strapless floral midi dress by Marchesa.
MTV Video Music Awards, 2008
Ahead of the MTV Video Music Awards, Lohan walked the marigold carpet in a belted violet micro-mini dress by Dolce & Gabbana.
InStyle Golden Globes After-Party, 2010
Even though she skipped the Golden Globes, Lohan made it to the InStyle after-party. She was a vision in a sparkly long-sleeve dress courtesy of Brian Lichtenberg, complete with a fashion-forward hood.
Liz & Dick Premiere, 2012
In honor of her Lifetime rom-com, Lohan stunned in an ivory floor-length gown. The trio of cutouts on her bodice (and the dangly red pendants) gave her attire a sultry finish.
Z100’s Jingle Ball, 2013
Back in ’13, Lohan went viral for her statement-making T-shirt dress from London-based designer, Ashish. She paired the “Same Old Chic” shirt with thigh-high leather Saint Laurent boots.
GQ Men of the Year Awards, 2014
Lohan’s zebra-print Balmain gown at the GQ Men of the Year Awards feels right up her alley.
Uno de 50 20th Anniversary Party, 2016
To celebrate Uno de 50’s 20th anniversary, Lohan styled a summery chiffon dress from Fendi in the jeweler’s signature color: crimson red.
MTV EMAs, 2018
After spending an entire summer in Mykonos, Lohan returned to the spotlight at the European Music Awards. She walked the step-and-repeat in a gold pleated mini dress from Saint Laurent — one of her all-time favorite ateliers.
Falling For Christmas Screening, 2022
Marking the start of the Lohanaissance (and the A-lister’s return to the silver screen), Lohan was all smiles at the premiere of her holiday film, Falling For Christmas. She looked every bit a leading lady in a semi-sheer floral gown from Valentino, a matching top-handle bag, and numerous diamonds courtesy of Stephanie Gottlieb.
Christian Siriano Runway Show, 2023
A few months before announcing her first pregnancy, the now mom-of-one secured a front-row seat at the Christian Siriano Fall/Winter 2023 show. As soon as she arrived, she instantly made headlines, thanks to her monochromatic bronze co-ord from the designer’s Pre-Fall 2023 collection.
Vanity Fair Oscar Party, 2024
Now a full-blown Balenciaga babe, the fashion muse got her hands on a design from the Spanish label’s Spring/Summer 2024 line for the Vanity Fair Oscar Party. The strapless number was covered in fringed sequins from head-to-toe, which looked chic alongside her Christian Louboutin platform pumps, diamond earrings, bracelet, and engagement ring — all from Joseph Saidian.
Our Little Secret Screening, 2024
After a jam-packed week of press tour appearances, Lohan celebrated the release of her second Netflix holiday film, Our Little Secret. Instead of going fully festive, she embraced her sensual side in a semi-sheer black gown from Zuhair Murad, which featured a plunging V-shaped neckline and shell-like accents.
On the accessories front, Lohan approved the mixed-metal trend with jewelry from Cartier and Briony Raymond.