It just kills me when my son wants to wear his red t-shirt, green sweat pants with an orange hoodie. I almost can't let him walk out the door. But, then I remember that he's just showing his new independent side and let him go. I used to convince him to wear matching clothes pretty easily when he was 6. He loved Sponge Bob and Sonic the Hedgehog, so I would either bribe him with a new toy or suggest clothes with these characters. It all started when I asked him to go pick out some pajamas to wear at bedtime. He came back with the first thing he could find in the drawer. It didn't matter what color it was, as long as it was comfortable. Of course, the more crazy he looked, the more I would comment on his color choices. So, I created a monster. Now he does it just to get me going.
When he picks out his school clothes, he tells me that this friend wears all purple to school and he wants to do that too. When I ask him if he will change his shirt or pants due to his fashion failure, he says, "I'm OK Mommy, I like this."
Now, my husband doesn't let him leave the house wearing all one color. Yesterday was St Patrick's Day and I was instructed to hide the green sweat pants so he couldn't wear them with his green shirt and hoodie. My son actually didn't even mention the green sweat pants, he just dressed in what I had put out for him and went to the bus stop.
There are two important things to remember when this dressing independence starts. One thing is that, when you look at all the other kids streaming through the halls of school, they are all dressed just as crazy as your kid. And when they want to wear all one color, remember that it has a great slimming effect.