DS wears a uniform for school, so I don't have to worry about that, he just picks which color shirt he wants to wear that day and he knows not to wear his white shirt on the days he has art

. Otherwise, he can wear what he wants as long as it is weather appropriate. He and I have always liked the same sorts of things when it comes to his clothes, so I am rarely surprised by what he chooses to wear.
DD loves dresses, so we have lots of those in her closet. She picks out most of her own clothes now and we haven't had any disagreements so far about what she picks out in the store to buy. That said, we go out in tutu's and ballet skirts over jeans or shorts on a regular basis

and although some people look at us funny (well, they look at me as if I'm the worst parent ever) most of the time we get comments to the effect of "Oh, it's nice you let her wear what she wants." and "Isn't she cute!" Just like my DS, I don't really care what she wears as long as it is weather appropriate.
And we keep their clothes in really good condition, so I don't worry about rips or holes. They are even good about bringing me their clothes if they spill something on them to put the stain releaser on them

; although we did have a hard time explaining to DD that water will not stain

.
The only time I pick their clothes is when we get pictures taken (family pictures, Christmas card pictures and pictures with Santa and the Easter Bunny) and they don't argue since any other time they get to pick their own clothes.