That Time Lindsay Lohan Wore Three Dresses To The Oscars

That Time When is Interview’s weekly trip through the pop cultural space-time continuum, where we return to some of the most overlooked moments from issues past. In this edition, we open up our June 2006 issue with cover star Lindsay Lohan, a woman of change, in honor of her 33rd birthday. 

The fiery redhead may have stolen viewers’ hearts with iconic movie roles in The Parent Trap and Mean Girls, but Lindsay Lohan was also an early-aughts fashion icon. Following her success in A Prairie Companion and Just My Luck, she spoke with Interview about her thriving movie career and, most importantly, her three different outfit changes at The Academy Awards. The most memorable moments of Lindsay’s night included spotting Madonna in an uncharacteristically bubblegum pink gown and receiving a helping hand from Winona Ryder as she jumped from one outfit to another. As she told Interview’s Ingrid Sischy in 2006 in an Elizabeth Taylor-inspired spread shot by Karl Lagerfeld:

INGRID SISCHY: You really like changes. How many times did you change at The Academy Awards? I remember I ran into you, and you were wearing one outfit and were about to change into another.

LINDSAY LOHAN: That night I had a little fashion moment with Madonna, who I think is a complete genius. She was wearing Versace and she goes to Guy [Ritchie, Madonna’s husband], Who’s wearing better Versace? And he didn’t say anything. Mine was this elegant, long gown. Hers was elegant as well. It was beautiful, pink, and I’d never seen Madonna in pale pink, and she looked gorgeous. It was just funny to have that moment. And then I ran to the bathroom to change because I promised my friend who works at Calvin Klein that I’d wear something from their line. I love them. They were all in there helping me change, including Winona Ryder. I was so embarrassed because I didn’t want to come off like a complete floozy. And actually, before I changed for the Vanity Fair Oscar party, I wore this amazing Christian Lacroix dress, so I ended up wearing three dresses that night.

SISCHY: But why were you changing so much? Because you promised all of these people you’d wear their clothes and it helps them when stars are photographed in their labels?

LOHAN: Because I make promises to friends, and I like to keep them, because I really appreciate all the clothes that I get on the racks and because I want to wear everything I see in every store and have it in pictures.

SISCHY: Fashion has a new muse, a 21st-century Audrey Hepburn. Someone who likes clothes.

Lohan’s extravagant dresses landed her on every tabloid known to man that March; one of the dresses from that night, a Christian Lacroix couture dress, has been forever emblazoned in internet history. Luckily for her, she had the opportunity to grace the red carpet several more times in the following years, wearing one extravagant dress after another.

After a few failed clothing line attempts over the years, her fashion industry rebirth was nothing shy of unexpected. In 2015, Lohan returned to the fashion scene once more in collaboration with Lavish Alice, a collection complete with everything from form-fitting navy mini dresses to bell-sleeved, soft gray sweaters. In a major plot twist, her clothing designs were professional and decidedly conservative. Today, the fashion muse can be found uploading glamorous throwbacks to her popular Instagram account posing like she’s on America’s Next Top Model or thriving in Mykonos on set of her reality TV show. Viva La Lohan!