Shimotsuma Monogatari ~ Kamikaze Girls.

A sweet Lolita outcast
A "yanki" delinquent

What is more to say?
A buddy comedy of course!

Kamikaze Girls is actually nothing more than a buddy film
BUT
it featured 2 of the biggest and recognisible Fashion Sub-culture of Japan.
Also it is a socio-comedy so other than just laughing along you might learn a lesson or 2.

So who else in Japan can you find if you want to get a Sweet Lolita that can act?While she is a really kinda aged for it (I grew up with her?) but she can probably take upon a role of a 17th for another 10 years (or even 20. LoL).
Kyoko Fukuda!
And it's no surprise!

http://www.kamikazegirls.net/