By Megan Riedlinger
2:00pm PDT, Jul 2, 2023
_
For the 2003 Teen Choice Awards, Lindsay Lohan wore a baby doll top left unbuttoned above the navel paired with low-waisted bootcut jeans and black strappy sandals. When it came to hair, the star went with a ubiquitous style at the time — a puffed-up half-updo.
MORE: The best reality TV shows of the 2000s
_
Remember this pink Dior print? The fabric was super-popular in the mid-aughts, partially due to stars like Lindsay Lohan and their affinity for the brand. She rocked a polo shirt featuring the print while stopping by "TRL" in January 2004, adding low-waisted denim and pointy-toe heels to complete her cool and casual look.
MORE: Stars at Fashion Week in the 2000s
_
Herve Leger bandage dresses were all the rage during the '00s decade, so this slinky black-and-white knee-length design on Lindsay Lohan was trending. The star, who wore the halter-style fitted frock to a Cartier event in June 2006, added another popular fashion item of the era — peep-toe pumps.
MORE: Paris Hilton's most delightfully '00s fashion moments
_
Here's a bold combo: Lindsay Lohan turned up at the MTV TRL Awards in New York City in February 2005 in this matronly pink lace midi-length dress, which would have been pretty forgettable on its own, but it was her outerwear choice that made this one wild — she topped it with a leopard-print fur coat!
_
It wouldn't be an aughts fashion gallery without some Juicy Couture! Lindsay Lohan rocked a teal set from the popular brand and added some weird accessories — a thin striped scarf and flip flops — while attending an event in Los Angeles in November 2002.
_
Lindsay Lohan went super casual for the ABC Primetime Preview Weekend at Disney's California Adventure in September 2003. The star headed to the amusement park in layered tanks — red and blue — and a denim miniskirt accessorized with red flip flops.
_
Lindsay Lohan embraced the boho style of 2006 while attending an event at Barneys New York that April, arriving in a spaghetti-strap white slip dress and capri-length bike shorts with a pair of peep-toe black heels.
_
The must-have accessory in 2006? An Alexander McQueen skull-covered scarf! Lindsay Lohan sported a blue-and-black version atop a funky black, white and blue blouse paired with gray jeans and knee-high black boots during New York Fashion Week that February.
_
Lindsay Lohan looked picture-perfect (and incredibly fashionable for the time) when she wore a baby pink blazer with low-rise denim jeans and open-toe heels to the Los Angeles "Chasing Liberty" premiere in 2004. She kept her accessories simple with a dainty silver necklace and matching pink clutch.
_
Opaque black tights don't pop up on red carpets often nowadays, but Lindsay Lohan sported the stark choice with a hot pink minidress at the Fall/Winter 2003 Nicole Miller fashion show in New York City that February. She added pointy-toe black kitten heels and a thick choker to complete her high-fashion ensemble.
_
Lindsay Lohan's darker locks were put on display when she attended the 2004 Teen Choice Awards. As for what she wore to the event? A fuchsia baby doll tank top with a turquoise embellishment, a cropped leather jacket, low-rise jeans and black sandals.
_
Here's a blast from the past: From the black choker necklace to the fitted tank to the camo-print pants and platform flip flops, every bit of the outfit Lindsay Lohan wore to the New York City premiere of "Dinner with Friends" screamed 2001.
_
Fingerless gloves? Yep, Lindsay Lohan added a pair — plus a trucker hat — to an equally laid-back ensemble as she headed to a Hollywood event in December 2002. She rocked layered tank tops (remember that trend?), jeans and white sneakers with her aught-era accessories.
_
Lindsay Lohan rocked a shimmery strapless green minidress at the premiere of "Freaky Friday" in August 2003. Her little frock included a black bow detail at the bust and a ruffled black hemline, which paired perfectly with strappy black heels.
_
Trucker hats on the red carpet? Looks like 2003 to us! Lindsay Lohan sported a cropped shiny black polo and low-waisted denim with pointy-toe pumps then accessorized with a black choker and a chunky white watch at a Stuff magazine pre-MTV Video Music Awards party that August.
_
Lindsay Lohan served up a chic look while stopping by the hottest show of the era — MTV's "TRL" — in December 2004. The star sported a band tee with a knitted vest over top and a pair of dark jeans with a very trendy shoe at the time — brown heeled knee-high boots.
_
In the early '00s, jeans were commonplace on the red carpet. Case in point? Lindsay Lohan's 2003 MTV Video Music Awards look — a long-sleeved white blouse with a black cropped vest over top paired with bootcut denim and pointy-toe black heels.
_
Things were a lot simpler back in 2003. Just look at what Lindsay Lohan wore to an event in New York City that October: a white tank, bootcut jeans and black heels. A black choker necklace dressed up this casual look a tad.
_
Super-low-waisted jeans and a black lacy crop top were a stylish choice in 2004. Lindsay Lohan wore the combo with pointy-toe black heels to the Teen People What's Next in New Talent party that January.
_
Now those are some boots! Lindsay Lohan attended a promotional event for "Freaky Friday" in New York City in August 2003 in these statement heeled boots paired with cuffed jeans, a black tank and a matching jacket.
_
Lindsay Lohan embraced the chunky belt trend at a movie premiere in New York City in August 2005, rocking a wide black belt atop a long-sleeved button-down blouse paired with bootcut jeans and ubiquitous black peep-toe heels.
