Lindsay Lohan’s rise to fame is unlike any other. After all, how many people can say they’ve starred in multiple iconic Y2K films like Mean Girls, Freaky Friday, and Confessions of a Teenage Drama Queen? The actress has been in the spotlight since she was a kid, and, over the years, fans have watched her grow up — and glow up — in front of the camera. When she starred as twins Hallie Parker and Annie James in The Parent Trap, her vibrant red hair and natural freckles set her apart amongst the era’s set of child stars. As Lohan transitioned into her teenage years, her look matured while still being playful. In the early 2000s, she fully embraced the trends of the time — think glossy lips, thin brows, and smoky eyes. Lohan has also tried out an assortment of hair colors, from deep red to bright blonde to jet black, as well as different vibes, from edgy to glam. Some looks stuck, others didn’t — but that’s all part of the fun, isn’t it?

For more than 25 years, Lohan has kept reinventing herself, showing she’s never afraid to experiment with her look. Take a stroll down memory lane below to see her full beauty evolution—maybe it’ll inspire you to switch up your own style.

Soft Layers In 1998

For the premiere of The Parent Trap, Lohan’s freckles and red hair are on full display. Her hair is worn down, and features simple, soft layers, perfect for her first red carpet.

Piece-y Blonde Highlights In 2002

Experimenting with color for the first time, Lohan rocked long, straight hair with chunky blonde highlights, creating a striking contrast against her natural shade.

Bangs In 2003

The actor showed up to the Freaky Friday premiere with long, straight hair and full, blunt bangs. Her smoky dark eyeliner paired perfectly with pink lips for a balanced and fresh look.

Inky Black Hair In 2005

For the 2005 American Music Awards, Lohan went for a major hair color change, dyeing her hair jet black. She channeled old Hollywood on the red carpet with soft curls and bold red lip.

Platinum Blonde In 2005

At a 2005 event in NYC, Lohan switched things up again with a bold new look. Her hair, which was now blonde, was cut into a blunt bob with dramatic side-swept bangs.

Smoky Eye In 2009

In the early aughts, Lohan was a big fan of the smoky eye — and it’s easy to see why. The sultry, smudged effect added depth and drama to her look while making her blue eyes pop.

Red Hair And Red Lip In 2012

Lohan went full old Hollywood glam for the premiere of her film Liz and Dick. Her rich red hair was styled in side-swept curls and paired with a bold red lip to match.

Halo Braid In 2013

Lohan returned to her strawberry blonde hair for a 2013 premiere, styling it in a halo braid. Combined with a peach lip color and winged liner, the look felt soft, romantic, and a little whimsical.

Bombshell Waves In 2023

After her time in Dubai, Lohan returned to the NYFW circuit in 2023. She turned heads at Christian Siriano’s show with a bouncy blowout, glowing bronze eyeshadow, and a glossy pink lip that pulled the whole look together.

Bright Pink Lip In 2025

Lohan stepped onto the red carpet at the Mexico City premiere of Freakier Friday in a magenta Balmain gown, her blonde hair pulled into a slightly tousled bun. But the real star of the show was her eye-catching pink lip, which was striking without being too over-the-top.