I very happily choose their outfits with care. I have to like it. In fact, as a Sim ages up, I generally whisk the entire family into cas.fulleditmode and change the newest Sims' wardrobe. Sometimes, I'll make minor changes to the others, too. However, in reality, since I have my own personal favorites, I don't change their clothing every day. Not enough time in a Sim day to do that. But, and this is a big BUT, if I see that a Sim is constantly wearing or has worn a particular outfit for too many days for my liking (as in I'm growing bored seeing it) I will stop them and change it out for another one.