I love American/French photographer-painter-filmmaker William Klein. He's been active for a while (since the 40s), and his work is still very relevant and contemporary. His images are quirky, lively, and always stylish - he's been intimately connected with the fashion world, having photographed for Vogue and directed some of the most remarkable fashion movies, including the cult classic "Who Are You, Polly Magoo?" (watch full version on Youtube here). The documentary "In and Out of Fashion" shows the best parts of his cinematographic work, and is a great introduction to his peculiar aesthetic. See some of it below:
This is the beginning of "Who Are You, Polly Magoo?" (1966) - see full version here.
This is an excerpt of "Mode en France", showing some of the best French designers of the 80s - and some of my favorites too, such as Christian Lacroix.
Learn more about William Klein in this NPR feature here.
*I once rented "In and Out of Fashion" at Odd Obsession in Bucktown.