'The Princess Diaries' Turns 25 — These Outfits Still Hold Up
Our take
The enduring appeal of "The Princess Diaries" is undeniable, and its 25th anniversary offers a lovely excuse to revisit the film’s surprisingly sophisticated fashion. While the movie’s humor and coming-of-age narrative resonated deeply with millennials, the wardrobe – a delightful blend of awkward teen and burgeoning royalty – has proven to be remarkably timeless. It's a testament to the film's styling that so many outfits still feel relevant today, influencing contemporary trends and inspiring recreations. This nostalgia isn’t just about remembering a beloved film; it speaks to a broader cultural fascination with transformation, self-discovery, and the quiet power of understated elegance. As we see with the style showcased by Gen Z stars at The Best Dressed Gen Z Stars At 'Variety' Power Of Young Hollywood 2026, a similar emphasis on polished, accessible looks continues to capture attention. The film’s ability to project a sense of aspirational style without resorting to overt extravagance aligns perfectly with the current mood of "quiet luxury," a trend that prioritizes quality, craftsmanship, and subtle sophistication.
What’s particularly striking is the way "The Princess Diaries" foreshadowed several style trends that have since cycled back into popularity. The emphasis on tailored separates, simple silhouettes, and a muted color palette – think classic trenches, crisp button-downs, and understated knitwear – feels remarkably aligned with contemporary aesthetics. Even Mia Thermopolis's initial, slightly clumsy attempts at royal dressing, with their oversized cardigans and ill-fitting skirts, hold a certain charm and resonate with a modern appreciation for comfortable, unpretentious style. It’s interesting to note how the film subtly championed a less-is-more approach to dressing, a philosophy that feels increasingly relevant in a world saturated with fast fashion and fleeting trends. This echoes the current conversation around mindful consumption, highlighted in articles like The Chicest Shoe Color Trend to Wear With White Jeans Isn't Black or White—It's This Neutral, where versatility and longevity are prioritized over fleeting novelty. The film’s influence extends beyond individual garments, subtly promoting a lifestyle characterized by understated grace and self-assuredness.
The film’s enduring legacy also speaks to the power of relatable representation. Mia's journey from awkward teenager to confident princess wasn’t solely about acquiring expensive clothes and jewels; it was about embracing her identity and finding her own voice. This resonates with a generation that values authenticity and self-expression. The film’s fashion choices, while stylish, always served the narrative, reflecting Mia’s evolving sense of self. We see this reflected in the broader conversation around personal style, where individuals are encouraged to curate wardrobes that authentically reflect their personalities and values, rather than adhering to rigid trends. The appeal of recreating these outfits isn’t simply about mimicking a specific look; it’s about tapping into the film’s themes of transformation and self-discovery, and expressing a desire for a more refined and intentional approach to style. Even the seemingly mundane aspects of Mia’s pre-princess wardrobe, like the Free People pieces many have embraced – as showcased in More Than Half of My Wardrobe Is Free People—The 15 Tops, Bottoms, and Dresses That Earn Me the Most Compliments – point to a broader shift towards comfortable, accessible, and effortlessly chic style.
Looking ahead, the continued fascination with "The Princess Diaries" and its fashion suggests a lasting cultural appetite for stories of personal growth and understated elegance. Will we see a renewed focus on timeless style and quality over fleeting trends, inspired by the film's enduring influence? Or will the nostalgia eventually fade, replaced by new sources of inspiration? Perhaps the most compelling question is this: How can we harness the film’s message of self-acceptance and intentional style to cultivate a more mindful and authentic approach to fashion in the years to come?
For millennials, The Princess Diaries is easily one of the most quotable movies. “What am I? A duck? ... Gupta, the queen is coming — to Grove High School.” But the film, which turns 25 this year, isn’t just beloved for its witty humor and top-notch acting. Anyone who watched it religiously in the early aughts (guilty) likely has a few outfits that still live rent-free in their head. Twenty-five years later, many of the film’s looks remain surprisingly relevant, continuing to inspire fashion today.
Costume designer Gary Jones was responsible for the wardrobe in both the original film and its sequel, The Princess Diaries 2: Royal Engagement, which was released three years later. Of course, The Princess Diaries is perhaps best remembered for one of the most iconic makeover scenes in movie history. You know the one: Mia Thermopolis (portrayed by Anne Hathaway) traded her unruly curls and bushy eyebrows for sleek, straight hair and perfectly groomed arches. Naturally, the transformation extended to her wardrobe, too. Gone were the old tees and frumpy pants, replaced by polished, princess-worthy ensembles that saw Mia embrace everything from playful prints to streamlined staples.
But Mia wasn’t the only style standout. Her archnemesis, Lana Thomas (Mandy Moore), delivered some of the film’s chicest Y2K looks — who could forget her bubblegum pink outfit at the end-of-year beach bash? Meanwhile, Mia’s artist mother, Helen, brought an eclectic, bohemian sensibility to the screen with quirky patterns and artisanal textures.
Ahead, revisit (and recreate) some of the best looks from The Princess Diaries — here’s hoping they endure another 25 years.
Corduroy Jacket + Striped Sweater + Wool Bucket Hat
Upon first glance, those unfamiliar with the film could easily mistake this photo for one taken today (it doesn’t hurt that Hathaway seems to be aging in reverse). That’s because many of the pieces — including the corduroy jacket, striped sweater, and wool bucket hat — still feel just as on-trend 25 years later. Consider this your cue to bookmark the outfit formula for fall.
Printed Blouse + Straight-Leg Jeans
For the aforementioned beach scene — which doubled as Mia’s first alone time with the ever-popular Josh Bryant — the newly minted princess paired a printed blouse with medium-wash denim and bright red wedge flip-flops, adding an unexpected splash of color to the beachy look. Eager to emulate the outfit? Just avoid stepping in any gum — IYKYK.
Crochet Cardigan + Rectangular Sunglasses
See? Helen was quite the fashionista, too. For a day of rock climbing, the artist opted for an unexpected combination: a colorful square-motif crochet top layered over leggings. (She did, however, remove the top before breaking a sweat.) If you’re skilled at crocheting, consider making your own one-of-a-kind version. If not, Etsy has you covered.
Pink Tank + Coordinating Polka Dot Skirt
Raise your hand if you still think about this outfit today. Because, well, same. For her performance at the beach party, Lana wore a shimmery hot pink turtleneck top with a colorful polka dot skirt, complete with teeny-tiny butterfly clips. It doesn’t get much more Y2K than that.
Button-Up + Tie + Plaid Skirt
You needn’t be enrolled in an elite school to embrace preppy dressing, which has maintained a strong hold on the fashion world over the past few years. A button-up shirt, tie, and plaid skirt may look a bit over the top together, but each piece works just as well on its own, pairing effortlessly with wardrobe staples like relaxed jeans and ribbed tanks.
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