This week is the 20th Anniversary of the theatrical release of Clueless (otherwise known as OMG has it really been that long??) And to celebrate, I thought I’d do a little something different on my blog today. I’m counting down my top 10 all-time favourite fashion movies. These are the movies that moved me, changed my perspective on style, or just plain tickled me!

Clueless itself is one of those movies that’s a big deal for me. It came out at the perfect time: I was 14 (spoiler alert!) and just starting to develop a sense of style. I was a suburban kid, one of the ‘plebes’ primed to look up to these rich kids with their enviable style. And it helped that the movie was based on Emma, and one of my main interests at the time was reading very old books.

But although it may have been the first fashion-heavy film that I’d ever seen, and arguably the most influential, it certainly wasn’t the last. Here are ten other movies, (nearly) in order of importance, that I’ve loved throughout the years:

10. Sex and the City 1 & 2

Plotwise, unnecessarily. Character Development, bordering on the ridiculous. And the fairy-tale ending of the show is a far cry from the fabulously ’90s gritty and true-to-the-(amazing)book first season of the series. But let’s just take a hot minute to appreciate the best of SATC. That is, the fashions. I mean, will you just look at every outfit in this scene, including the sales girl’s? Aspirational style, indeed:

9. The Fifth Element

As an avid sci fi and fantasy fan, I definitely watch a lot more epic adventure movies than I do fashion heavy chick flicks. And while many speculative fiction movies feature amazing costumes designed by highly talented costume designers, I had to put The Fifth Element on the list. It’s one of those movies that’s so bad it’s good, and I rewatch it whenever I need a silly pick-me-up.

However, it’s on this list for the little known fact that not only did Jean Paul Gaultier design the clothes and 1997 fashion darling Milla Jovovich star, but if you look closely you can spot other fashion folks du jour throughout the film. I mean, this scene! It’s a fashion film and you wouldn’t even know it:

8. Coco Avant Chanel

This was a fascinating look at the figure behind the double CC logo that every fashion girl seems to covet. It may be a status symbol now, but once Coco was a stage girl. The movie is required viewing for anyone with an interest in fashion, if only to disabuse you of the notion that Chanel has always been Karl Lagerfeld.

7. Funny Face

A movie about a bookish, philosophically-obsessed girl who gets to travel to Paris, hang in an Avant Garde bar and become a model? Um, yes! This is the first movie on the list featuring a fashion magazine editor, but I think you know it won’t be the last. I love the opening scene. The character of Ms. Prescott is more likely based on one of her predecessors, but can you imagine Anna Wintour running Vogue like this:

6. Pretty in Pink

Speaking of pink, this movie. Set during the ’80s recession that wasn’t quite as bad as the ’08 crisis, Molly Ringwald’s character embodies that DIY spirit that overcame us up until the last couple years. And the character Iona? With her frequent clothing changes and her way of dressing like every day is halloween? Well, she’s just everything I want to be when I grow up (uhhhhh….).

5. Zoolander

You knew it had to make the list. And with the second one finally in production, there couldn’t be a better time to have a laugh at the comical and dangerous world of male modeling. Man I love this movie:

3. The Devil Wears Prada

I had to do these next two out of order, and you’ll see why in a moment. The Devil Wears Prada is the movie the entire fashion industry loves to quote. Based on the book by former Vogue Assistant Lauren Weisberger, I remember seeing the pre-movie cover of the roman a clef and it just called to me. Why did I devour it, and why did I love it and the movie. This scene is pretty much explains it:

4. The September Issue

Released not long after the Devil Wears Prada became a thing, this is the last of my movies about the editor of a fashion magazine. And it’s placed after the Devil Wears Prada since I see it as Conde Nast’s response to the skewing fictionalized film. It’s an edited inside peek into what is, for many people, the biggest name in fashion. Fascinating, but I always prefer fiction over real life:

2. Breakfast at Tiffany’s

Other than the iconic jewelry store made even more famous by this film, there’s Holly Golightly. She may be deeply troubled, but you can’t argue that she exudes style in every frame. I mean, that sleeping mask? How long have I coveted one just like it?

1. Marie Antoinette

I have a particular fondness for this movie. It came out in theatres when I was 25, and it is so everything about being young, fun, girly, and obsessed with pastels. I even remember sitting in the theatre watching the trailer. I thought to myself: a period costume drama with a modern soundtrack? Are you kidding me? This movie was made for me! It is so 2006, so pre-economic crisis, it is everything:

There it is! My list of the movies that has defined my thinking about style and about fashion. And it all comes down to this: I love the clothes. Sure, tomorrow I’ll go back to championing clean beauty and sustainable style. But this is why we do it, right? For the love of beauty, and style, and our dreams, fictionalized or not, of fashion.

What about you? What are your favourite fashion films? And how are you celebrating the 20th Anniversary of Clueless this week? Rewatching it, I hope!! 🙂

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