I very rarely dress DD in 'pretty' clothes. Yes, I try to make sure that she looks presentable when we go out (eg, make sure she is not covered in her most recent meal), but I would say that I tend to dress her in more practical clothes than pretty clothes. She has very rarely ever been put in a dress (although I did for her birthday) - the last time I put her in one it made crawling too hard so she was out of it quick smart.

I guess my frame of mind when I dress her (or buy clothes for her) is:
1. What's fairly cheap so I don't mind if it's ruined by being stained or getting holes in it by crawling around our backyard
2. What is going to be comfortable and not restrict movement

I know this is a slightly different topic, but I sometimes feel sorry for little girls who are dressed in clothes and shoes that they can't run around in (when they are in a situation that's appropriate to do that). In my humble opinion I feel it doesn't help them develop their gross motor skills.