Hellobee Boards

Well, I can't say it will sink in and maybe this doesn't apply to boys, but my husband dresses my daughter in the morning and even if I lay out her clothes, he manages to pair the "wrong" socks or hair bow or shoes.

-Pink and red should never be mixed except on Valentine's day (this is his biggest offense and he tries to commit it almost daily. I sometimes wonder if he is color blind, but he says he isn't).
- if you have a color "theme" for your shirt and pants, don't throw a brand new color into the mix with socks and shoes
-don't wear holiday themed shirts on days that aren't that holiday
-don't wear long sleeves with shorts, or short sleeves with wintery pants (because one piece is going to be inappropriate for the weather unless you are layering).
-maybe don't mix prints? I actually love print mixing, but there are a lot of ways it can go wrong, I guess.

Everything else, I let him do what he wants.

The only things I can think of are to maybe limit his choices when you buy the clothes and what you make available in his closet/drawers. I dress my son very simply, you will see him in a pair of solid pants, a striped tee with long sleeves and a fleece vest in the winter. In the summer, I get a little more crazy with prints because I can not pass up a pair of madras shorts.

Yeah when she picks her own clothes as long as it's weather appropriate I don't really care that it doesn't match or is a fashion faux pas. They're kids! I just shake my head and laugh.

We are in the 'crazy' phase, which I just think is fun self expression. I tend to buy interesting tops and simple (black or denim leggings, denim shorts, solid color bike shorts) bottoms, so choices are fairly simple. But I love to see what my daughter comes up with.

I kind of agree on "meh". We let C pick her own outfits sometimes and it's inevitably something ridiculous (like a princess dress, or a billion layers of random stuff, or her swimming life jacket). We just let her wear it.

@Anagram: this made me chuckle.