I'm all for letting it all hang out, but it's also nice to be all buttoned up! While there are different challenges between painting the clothed and unclothed, usually the biggest one is deciding on the outfit, picking the style and colors. For myself, I just like what I like, and am not up on the current fashion rules (are skinny ties in? are vests frowned upon? where are we regarding socks?). So for paintings, I'll gauge what's on TV and the internet, and try to opt for something that seems classic and not trendy.