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When should kids be allowed to dress themselves?

Do your kids get to pick their own clothes?

And what you think it's important for your kids to know about style and their clothing choices? 

I have mostly let my children pick their own clothes, partly for ease, partly because I want them to have a good sense of what they like and dislike.  I just read a great article that included many other benefits of allowing children to choose their own clothing.  Some of the benefits were things I'd never thought of before.

Let kids choose clothing

Even though I allow my kids lots of leeway when it comes to what they're wearing, I still think they need to know about what the norms are in society so that they can make conscious choices about how they present themselves to the world.  And sometimes I don't give them as much choice.  For certain functions it's appropriate to dress up;  you will wear holes in your PJ's if you play outside in them and I am not willing to see that happen, and you've got to wear shoes in restaurants.

What about other times though?  A few weeks ago we went on a homeschool group field trip and I found myself cringing a little when I looked at my kind of grubby looking kids next to the rest of the more polished group.  I hadn't realized how stained the clothes were that they'd put on that morning until I saw them in a larger group.  Now I wonder if I ought to pay a bit more attention before events like that.  I think that society in general, treats people better when they look better.  Personally, I feel better about myself when I am more put together as well.

So, how do I support my children's independence and help them look their best as well?  Or is that important yet?  The reality is that I don't have it in me to, nor do I want to, pick out all their clothes.  I have “dress nice” clothes set aside for things like weddings, but perhaps I ought to put some aside for “outside the home” wear as well?  Or do you think that at these ages (about 2, 5 and 7) having free reign is the best idea?