Mary-Kate and Ashley Olsen's Best Outfits from the 2000s

Few things in this world hold quite as much significance for me as Mary-Kate and Ashley Olsen did in the early to mid 2000s. As a preteen, I collected Two of a Kind and So Little Time books and read every single one; I watched “Holiday in the Sun” so religiously that I can still quote the lines with more accuracy than I could “Mean Girls”; I seethed with jealousy at anyone whose parents shelled out for a “Sail with the Stars” cruise.

As a teenager, my obsession shifted over to their style (slightly more socially acceptable, but still a little creepy in retrospect). I joined forums such as Trenchcoat Twins, Olsen Paparazzi World, and The Fashion Spot—the latter of which, at least, I credit for getting me into fashion in high school—and racked up thousands of posts; I trawled vintage stores and flea markets for slouchy T-shirts, slipdresses, and cowboy boots; I even ended up at New York University (OK—I didn’t really apply because that’s where they went, but I can’t pretend it didn’t plant the seed).

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If Instagram had been around back then, I definitely would have run one of those outfit ID accounts to document every last piece in their closet, so important did it seem to know exactly where they bought their clothes. If only I could imitate their wardrobe, I believe the thinking was, then maybe I could harness whatever it was that made them so captivating. Even back then, they were starting to become less accessible—they grinned less on the red carpet and hid from the paparazzi behind giant Balenciaga City bags (oh, to own one of those; the real American dream)—which, to a generation of teenage girls, made them all the more enigmatic.

Clearly, I wasn’t the only one obsessed: This spring, a couple of Brooklynites opened a pop-up museum dedicated to the twins, with rooms filled with binders of magazine clippings, a giant prop Blackberry and Hermès handbag, a re-creation of Mary-Kate’s cigarette-filled wedding, and walls of paintings by artist Laura Collins of the Olsens hiding from the paparazzi.

Today, Ashley and Mary-Kate turn 30, and they’ve clearly worked hard this past decade to shrug off their child-star image (and get everyone to stop calling them “the Olsen twins,” goddammit). With the success of their brands the Row and Elizabeth and James—not to mention their impressive commitment to never smiling in photographs—it’s safe to say that by now, there’s no danger of them not being taken seriously.

And while I’ll still reliably love anything they wear today, there’s a part of me that misses the much-maligned “bobo” days (“bohemian” meets “hobo,” for those unfamiliar) of absurdly oversized sweaters, ripped jeans, and circle scarves. So, in honor of their birthday, we’re taking a trip back in time to 2004–2008, when Mary-Kate and Ashley Olsen’s outfits reigned supreme.

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