Marie Laurencin – Mademoiselle Chanel

This is Marie Laurencin's Mademoiselle Chanel, portraying Gabrielle "Coco" Chanel, founder of the fashion house we all know today.

It was painted when Chanel was forty, already a woman of considerable wealth and fame. Laurencin, though a known name herself, was only just beginning to build a career as a portraitist — meaning a famous subject sat for a painter still relatively new to portraiture.

Chanel, as the story goes, disliked the result and refused to buy it. The exact reason was never confirmed, but there's no shortage of theories. One holds that the sitter's noticeably melancholy expression — revealing the tired, vulnerable side behind a successful businesswoman's public face — was something Chanel simply didn't want shown. Others suggest it simply didn't look like her, though judged on its own terms, the painting is hardly poorly made.