Movie Wardrobes I Can't Stop Thinking About

Times change. Fashion is forever.

If I were a contestant on Room Raiders, my closet would stump even the most diligent of sleuths. Some days I dress exactly like my husband, and others, I channel my best Barbie. My style is all over the place—and often my outfits end up as total flops—but it’s shaped heavily by the media I loved as a kid.

There’s a reason why 90s fashion has had precisely 17 revivals since the decade ended 25 years ago (🤮). People had fun with fashion, and styles were diverse. 00s fashion, on the other hand, was a little less cute—why did we wear so many layers?—but there are still moments from early in the millennium that are forever on my mind.

These are the outfits (and movies!) that I just can’t stop thinking about.

Casper Meets Wendy (1998)

GIF by GoPlay

Gif by GoPlay_be on Giphy

The original Casper is one of my all-time favorites. It gave us one of two 1995 pairings of Christina Ricci and Devon Sawa (Now and Then is the other) and it was made at exactly the right moment in CGI history, IMO. But Casper Meets Wendy is a perfect companion starring pre-Lizzie McGuire Hilary Duff and a second Casper-universe appearance from raspy-voiced queen Cathy Moriarty (as a completely different character, I might add).

It had ghosts, witches, ultra-tan George Hamilton, and the best red overalls and matching bucket hat combo I ever did see. Wendy wears an entirely red wardrobe, and every piece is as cute as the last, but I thought about those overalls for years. Finally, as an adult, I found my own red pair at Forever 21. They weren’t shorts like Wendy’s, and I never did get a matching hat, but I wore those overalls until I could no longer close the side zipper. I will be searching for a new pair this summer.

Wish Upon A Star (1996)

still from Wish Upon a Star

There’s a lot about our childhoods to reminisce about. The economy wasn’t constantly tanking, regular humans could afford houses, and as we’ve established, the fashion was superior. But we never talk about how the movies and TV shows made for kids and young adults were actually good. Have you watched anything made for kids lately? They’re bad! And not just bad because I’m now pushing 30, but it’s genuinely dumbed down. We had true cinema and it’s still great to watch today.

Wish Upon a Star is among the best of Disney’s movies—though I always think it’s a Disney Channel Original, it isn’t—and I’ve been trying to recreate every outfit my entire life. The blue polka dot skirt and pleather vest that Katherine Heigl’s Alexia Wheaton wears is obviously perfection and I have to imagine my mini skirt + thigh-high sock obsession started here. Alexia’s best, however, is the purple outfit with white pumps and frosty makeup that opens the movie. I’m not alone in this ranking. Buzzfeed agrees, and just a year ago someone pleaded with r/findfashion for help recreating it, though it’s sadly remained answerless.

Looking back at Wish Upon a Star’s wardrobe, I realize that I am every one of these outfits. I am Hayley Wheaton’s baggy t-shirt and denim jacket. I am Alexia’s ultra-feminine style. And sometimes, I’m even that dominatrix-esque two-piece that Alexia-in-Hayley’s-body wears while she dances on the lunch table.

As a socially awkward kid with hair she couldn’t manage and an affinity for red Dickies, I desperately wanted to be an Alexia. She was effortlessly cool and beautiful. She drove a Jeep! I was more of a Hayley, though, always feeling other (and bad at driving).

My Date With the President’s Daughter (1998)

still from My Date With the President’s Daughter

Yep, we’re talking about that pink dress. I’m not sure if a single outfit has defined a generation more. The spaghetti strap, white-trimmed, baby pink velvet mini dress is the epitome of a 1998 cool girl and it physically hurts that I don’t have it. It hurts even more to find out someone bought the actual movie costume for $15 from Depop.

As Hallie emerged from the dressing room at the mall, I watched with as much amazement as Duncan did (played by Boy Meets World's cute older brother Will Friedle). I’ve long tried to find something close. First, it was a crop top from Urban. It was the right shade of pink and had white trim but it was still just a shirt—though I should add that one time while wearing it, someone immediately compared it to this movie. A few years later, I bought a pink velvet dress but it was too deep a pink and had thick straps. Everything is always a little too this, a little too that. If I ever have $99 to blow on a single thing, I might just get my own pink dress made to order. It seems only right.

When Disney+ started, I was unreasonably excited for all the movies I could finally watch again, but I was heartbroken that My Date With the President’s Daughter wasn’t there. There are a few others that didn’t make it either, like the first Under Wraps, Susie Q, and Life Size (Wish Upon a Star is at least available on Prime). For now, I’ll have to watch painfully blurry versions on YouTube while I dream about that dress.

Josie and the Pussycats (2001)

still from Josie and the Pussycats

I can’t put into words just how important the Josie and the Pussycats movie is to me. I still have the soundtrack in my car, which I listen to on repeat as if it were an actual band’s album. I dreamed of being named Josie instead of Medea, which teachers couldn’t pronounce and everyone made fun of. I loved the movie then and I love it now that I finally get all the jokes.

I would wear literally every piece of clothing shown in this movie, but the leopard print suit with clear Pleaser heels is my #1. If I owned this, I would wear it to work, to the bar, to the grocery store. You’d have to bury me in it.

A few years ago I even shamelessly DMed the movie’s costume designer on Instagram trying to figure out how I could possibly own something similar. She didn’t answer (shocking), and tbh it’s probably good because if it did exist outside of this movie, I couldn’t afford it anyway.

I have no way of knowing if this movie is why I’m so obsessed with leopard print but I imagine it didn’t hurt.

my DIY Josie costume

In the movie, everything deemed cool is immediately scooped up by trend-hungry teenagers. In real life, the Halloween costumes that year also quickly flew off the shelves. I was desperate to be Josie, but we couldn’t find the official costumes anywhere. My heart broke a little more with every store we visited. Eventually, my mom put together her own version, which was more akin to the cartoon Josie than the Rachael Leigh Cook version. The print was wrong. I was pissed.

Practical Magic (1998)

still from Practical Magic

If half my personality is Josie and the Pussycats, then the other half is Practical Magic. It’s a defining movie in my life that I watch when I’m sad, when I’m happy, when the first crisp air of fall rolls in. I dream of living in that house with my sisters—I literally daydream about winning the lottery and building a replica somewhere in New England where I can tend to my garden all day. But this isn’t about houses, it’s about clothes and these witches have gorgeous closets. 1998 was a very good year for wardrobes.

Y2K fashion has come back, but it’s not exactly what we wore back then. When people dress like the 90s, however, it’s basically everything worn in this film. Long flowy skirts and little tops, very good sweaters, meshy floral dresses, and velvet witchy robes. It’s perfectly whimsigoth and everyone who secretly tried blowing on candles to light them has probably dressed like this at some point. Gillian’s green velvet dress is a standout, as is Sally’s jean shorts, baby tee, and rain boots combo.

Clueless (1995)

stacey dash closet GIF


Clueless was obviously going to be on this list. Cher Horowitz might have the most recreated wardrobe—and coveted closet—popping up in music videos and Halloween parties for eternity. Cher walked so Alexia Wheaton could run.

still from Clueless

Everybody has a favorite Clueless outfit. Is it the yellow plaid? The Alaïa dress? The white Calvin Klein? I’d wear any and all of the above, but my favorite is the argyle skirt, sheer top, and cropped sweater Cher wears while failing her driver’s test. Ugh, what a betty.

Shania Twain - That Don’t Impress Me Much (1997)

It may not be a movie but this music video deserves to be on this list. A three-piece leopard print outfit with matching boots and suitcase? Are you kidding? (I told you I was obsessed with leopard print!) Shania taught me to be fashionable and she also taught me to not be impressed by men. Win/win.

ⓕ On February 4, 2004, Mark Zuckerberg started (The) Facebook from his dorm room at Harvard. It’s become one of the most used, and most hated, platforms. I’ll never forgive it for killing Myspace.

🌐 In February of 2007,  Tumblr was publicly released. The easy-to-use microblogging site became a haven, especially for young alt millennials trying to find a space for themselves. Notably, some of the most popular content was the porn, which Yahoo removed when it bought the site. It has lost some of its appeal over the years, but famous gen-zer Brittany Broski is on the site again, so maybe it’s destined to return.

💿 February 1, 1994: Green Day’s Dookie album is released. 30 years later and the band is still making people mad with their political stances because apparently American Idiot wasn’t obvious enough.
👠 February 2, 2001: Head Over Heels is released, a movie about living with hot models and having $500 rent in New York. Oh yeah and a potential murder mystery and FBI sting. And heartthrob Freddie Prinze Jr.
🫀 February 12, 1993: The bizarre but romantic Untamed Heart is released. Many years later I would watch this on repeat after a breakup, fast-forwarding through all the scenes Christian Slater wasn’t in. Sue me.

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Not every month will have a theme, but in February we’re sticking with fashion. See you in two weeks for an ode to Juicy Couture.