It's not particularly difficult to find an article or blog post about fashion in movies and find ways to put together Clueless or Heathers-esque outfits. That is not stopping me from writing this. In addition to those movies, I want to point out a few more films that can be considered sources of outfit inspiration. However, instead of just focusing on emulating the actual outfits worn by the characters, I want to use the feeling you get from watching a particular film to create an outfit. Yeah, we're about to get really touchy-feely in here.
There is something about this movie that has made me watch it over and over again since it was released in 2007. It boasts some sort of lesson about being yourself, which is apparent when you compare Nancy's (Emma Roberts) outfit with the other furry boot-wearing popular girls in the film. The salesgirl in the above photo recognizes Nancy's originality, saying that she "loves the sincerity." That makes my inartistic self want to go gather a bunch of random fabrics and sew them together to create an outfit that's only awesome to me and about two other people. This film is a great one to watch if you want inspiration for an ultra sincere/preppy detective vibe. Let's just say I went out and bought penny loafers after my first viewing.
On the opposite end of the spectrum, the classic 1988 film Heathers portrays the preppy look (and lifestyle) in a very dark and ironic manner. The plaids and colorful tights are worn by girls who make the Mean Girls look like misunderstood sweethearts. The brightness of their clothing make the morbid occurrences of murder and suicide look positively stylish. I'm not saying you should dress like the Heathers in preparation for some deadly activities, but there's nothing wrong with being influenced by their bitchtastic style. Also, remember the higher the shoulder pads, the more power you will hold.
Nothing says "childish whimsy" quite like Matilda, which I find to be a sorely underrated film. I mean, the kid develops psychokinesis because she isn't using her brain enough! There's a message there about the consequences of not valuing education. Whatever. Miss Honey's overalls may appear childish in 2011, but I think they speak volumes of her sweetly optimistic personality. The green world setting of her humble abode make such an outfit possible, and inspires one to throw on a pair of denim overalls and hang out in the grass with a good book. (Okay, perhaps not everyone would ever be inspired to put on overalls. To each his/her own.)
Speaking of childish whimsy (and overalls), I love the role reversal (that is especially evident in the above photo) of the two main characters in Uptown Girls. In this movie, which critics hated but I've always adored, Molly (Brittany Murphy) is the free-spirited adult who refuses to grow up and Ray (Dakota Fanning) is the uptight ballerina who won't let loose. Since Molly lives a fairy tale life, she dons a wide assortment of pretty dresses and flowy skirts (did I mention the overalls?), which contrasts well with Ray's structured school uniform. Anyone looking for inspiration for a princess-like outfit should watch this movie.
We end with an epic movie that supports this theory: If you put effort into how you look, you will end up looking better than everyone else. In a bonus feature on the Clueless DVD, writer/director Amy Heckerling talks about how the tendency of 1995 high school kids to dress like dirty supporters of the grunge movement ultimately provoked Cher to dress the way she did. This means lots of plaid (jackets and skirts, not flannel), knee-high socks, headbands, and of course, that notorious Calvin Klein dress. She taught us that it is worth the effort it takes to look good. Putting an outfit together carefully reflects a creative mindset that understands and respects the fact that other people are going to be subjected to look at him or her.