I'm so glad someone finally wrote about this-- it's like the phenomenon of women dressing to impress other women. I love my boyfriend, but he wouldn't care if I never wore makeup and started wearing my asics
See also: this girl from Elle.com's Daily Street Style in difficult-to-wear-but-she-pulls-it-off-like-gangbusters-pants; and, also, Carrie Bradshaw. Most men will tell you she dresses like a hobo or a child playing dress-up but ask most women and they will set you straight.
*okay, honesty-police, when another blogger links to a blog and I read it
(photo credit: photo #1: elle.com, by courtney d'alesio, photo #2: fabsugar.com)