Lindsay Lohan's Best and Worst Beauty Moments

Like any 17-year-old, Lohan is overenthusiastic with her flatiron and eyeliner pencil. The ingenue's dewy skin and full cheeks are still sweetly refreshing, though.

The trucker hat trend is Ashton Kutcher's fault, but Lohan's attempt to shed her teen-princess image with blunt bangs, harsh eye makeup, and a choker necklace is an unwelcome shift for this girly-girl.

Lohan's bronzed skin, softly curled hair, and poppy pink lipstick standout next to a pre-30 Rock Tina Fey.

Embracing her dark side (we're talking about her hair color!), Lohan slowly starts to run in older, faster circles on account of her newfound fame.

Clutching one of four awards she would win that night, a busty Lohan should have selected a larger top for this tween-centric event.

Ten months later, an 18-year-old blonder, thinner Lohan racks up Golden Popcorn awards for her performance in Mean Girls.

Channeling vintage Hollywood, Lohan now outshines her dubious BFF with a red lip and sophisticated updo.

Lohan starts to look scary skinny as she hits the red carpet for Brangelina's big movie. Her second album A Little More Personal (Raw) will drop later that year.

Fresh off the success of Herbie: Fully Loaded, a college-aged Lohan graduates to mature platinum side-bangs and bronze-free skin.

Lohan shade-switches to a beautiful, new mahogany color. Perhaps she was inspired by her rumored boyfriend at the time, Jared Leto.

Mother, Dina—who was in the middle of a messy and public divorce—proudly wraps her arms around her dazzling daughter before this Robert Altman flick. One year later, salacious photos taken around this time surfaced of Lohan engaging in erotic "knife play" with Vanessa Minnillo.

While exiting a boat in this tiny green dress, Lohan—sans underwear—accidentally flashes paparazzi.

Fresh from her split with Harry Morton, Lohan rocks a fantastic half-up, half-down 'do while promoting Bobby.

Two months after she's hospitalized for dehydration while filming Georgia Rule, Lohan fumbles with a tipsy tiara.

Lohan can't hide her confusion—or her glazed-over eyes—in this unflattering pic after getting booked for a DUI, cocaine possession, transporting a narcotic into a custody facility, and driving on a suspended license.

While on probation, a dry Lohan makes no effort to conceal her court-ordered alcohol detection SCRAM bracelet.

In the midst of her legal woes, Lohan manages to rock these ombre highlights (two years before the look became trendy!) and flawless makeup. The budding entrepreneur also was busy designing her 6126 leggings line and prepping for the 2009 launch of her Sevin Nyne sunless tanner.

In the midst of her boho phase, Lohan—and her super-long extensions—were overdue for touch-up.

A puffy-faced Lohan poses before the debut of her soon-to-be-panned fashion collection at Paris Fashion Week.

A bedazzled fedora (really, Lindsay?) doesn't distract anyone from Lohan's lifeless ponytail—or her increasingly risqué lifestyle. Her BBC documentary on sex-trafficking in India (it came out two months later) reminds critics that perhaps this party girl can still reform.

Lohan exits a friend's house with suspicious powder markings on her foot.

Lohan doesn't disguise her feelings with this provocative—and expletive-laced—manicure before getting sentenced to 90 days in jail for violating probation for her 2007 charges. She will spend only 23 days behind bars before being released into mandatory rehab.

After three months at Betty Ford (she left in January), Lohan looks healthy and happy. Despite facing felony grand theft charges for a stolen necklace, the proven comedienne hits a home-run with this late-night spoof.