If I could draw well enough (or had the time to practise) I would definitely join the What I Wore Today Drawings group on Flickr. My favourite artist by far is Caitlin Shearer. Her beautiful watercolours, make even the most basic of outfits covetable...I never wanted a Cats The Musical sweatshirt before, but I want one now..I love the annotations to each outfit - "Free wine is good wine"? Well said.
More on Caitlin's blog: http://caitlinquiet.blogspot.com/