Where: The Anna and the King movie premiere in 1999
Why we love it: Matching flipped-out hair is #TBT worthy.
Where: 2001’s Rush Hour 2 premiere
Why we love it: Straight hair with chunky highlights is aughties glam at its finest.
Where: Vanity Fair’s Annual Oscar party in 2002
Why we love it: No more matchy matchy! Ashley ops for soon-to-be signature waves, while Mary-Kate sticks with pin straight. A nude lip finishes the look.
Where: Opening of Fox Sports Grill in 2003
Why we love it: Mary-Kate may regret that hat, but a pink lip is always in style.
Where: The 2003 MTV Video Music Awards
Why we love it: We’re sweet on this honey-blond hue.
Where: The premiere of their 2004 movie New York Minute
Why we love it: Olsen twins who? Ashley and Mary-Kate’s once-identical beauty looks start to diverge even more.
Where: The 2004 MTV Video Music Awards
Why we love it: Team blond or team brunette? We can’t pick. Can you?
Where: New York City’s Ace Gala Awards in November 2005
Why we love it: Looks like the sisters got matching spray tans. The bronze glow really brings out their gorgeous eyes.
Where: The Met Gala in 2005
Why we love it: The twins go boho to celebrate Chanel at the Met Gala.
Where: Front row at Olympus Fashion Week in 2005
Why we love it: With messy hair and minimal makeup, these future fashion designers look like laid-back students.
Where: The 2007 Golden Globes after-party
Why we love it: World, meet MK and Ashley 2.0. This marked their transformation into the grunge glam beauty icons we know today.
Where: Farce of the Penguins release party in 2007
Why we love it: Matching outfits is bad. But matching red lips? Always a do.
Where: The 2008 launch of their clothing line Elizabeth and James in London
Why we love it: Back to their signature blond hair.
Where: The Museum of Modern Art’s 2009 film benefit honouring Tim Burton
Why we love it: Sorry, Ashley, but Mary-Kate is slaying with this bold lip.
Where: The launch of Marktbeauty.com in 2010
Why we love it: Blowout goals.
Where: In New York City at the 2014 World of Children Awards
Why we love it: The MK and Ashley we know and love.
Where: The 2015 CFDA Awards
Why we love it: Centre parts take centre stage with this red-carpet look.
Where: The Met Gala in 2016
Why we love it: Behold, the modern-day Olsen: bed-head, neutral makeup and so much smoulder.