Secretly Stylish: Lilly Moscovitz from The Princess Diaries

When I first watched The Princess Diaries, I was simultaneously amused and conflicted about a scene appearing early on in the film, in which our heroine, Mia, is transformed from a frizzy-haired, glasses-wearing teen, to a sleek-haired, designer-backpack carrying princess. As a young girl with a head of frizzy hair and glasses myself, I was wary of the initial ugly duckling narrative, only to realize that the very point of the film is to underscore the triviality of superficial changes—it’s whats on the inside, as they say, that counts. However, revisiting the movie as an adult (one that writes primarily about style and fashion, I should add), I realize that a “looks don’t matter” reading of the film risks ignoring one of the best parts of the movie: the character of best friend, Lilly Moscovitz.

Lilly proves that looks—or, more specifically, personal style—are central to self expression and, in a movie that opens with a typical geek-to-chic transformation, Lilly Moscovitz stands as a confident witness—marching to the beat of her own style-drum and never wary of telling it like it is. For our latest installment of Secretly Stylish, we’re shifting the spotlight to a few features of this fashion-forward best friend’s wardrobe.


For many students required to wear a uniform, style risks falls by the wayside. Lilly embraces the challenge fully, relying on accessories and unique hair styling to give her ensemble personal flair. Here, she rocks an early-2000’s favorite—intricate hair twists using multi-colored hair ties. I went to a school with uniforms and a strict “no more than two rings per hand” policy, so Lilly’s ring-coated hand looks extra-edgy against her pleated skirt.

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Even in her gym sweats, Lilly manages to show off her exuberant style. Though her countless butterfly clips and a thick chain collar place her firmly within the early ’00s, her otter backpack—a shoutout to Lilly’s animal activism— is a timeless example of how fashion can work to express elements of your personality. Did I mention it’s pretty cute, too? I don’t know about you all, but I know I definitely wanted one after seeing hers.

There is so much going on in this image that it’s hard to know where to begin. Casually hanging out by her locker, Lilly piles on the accessories, offering yet another example of innovative hair styling. Here, she opts for a high, half-ponytail, held in place by an ornate clip. In addition to her multiple rings and collar, she adds several beaded bracelets, adding a bohemian touch to her pseudo-punk style. Lastly, can we discuss those bumper stickers? With her World Wildlife Fund membership plastered on her locker door and her expression grave, there’s no doubting Lilly is serious about her commitment to rainforests, and that type of earnest passion for a worthy cause never goes out of fashion.

What was your favorite Lilly moment—fashion related or otherwise? Let us know!

Posted 4 years Ago
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