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N loves picking his shirts and shoes. Pants on the other hand, who needs pants.
E on the other hand would be a very happy nudist.

Every day. When she goes to preschool she'll have some guidelines for school days but she will still pick.

If I let him pick he'd probably want to wear his fleece Dalmatian costume from Halloween every day . He usually doesn't really notice/care about his clothes though. It'll be interesting with a girl next to see if she's any different.

Uhh, do I have a choice!?!? Lol

She always picks her own clothes! I try to only keep things out that I like so I don't care too much.

As long as it's weather appropriate,
I couldn't care less what she wears as long as she is happy!

Yes she likes to pick. Lately I just ask if she wants pants and a shirt or a dress, the open the drawer and let her pick one part (a shirt) then I pick pants that match. Or, often shes chooses a pair of tights and I steer her towards an outfit that works with those tights. If I really want her to wear something specific I talk it up before that day so she's excited to wear it.

She would wear her "sparkly shoes" (ballet flats) every day but they aren't practical and she can see they are getting worn out, so she accepts that sometimes she has to wear other shoes.

She's also started putting her pants on by herself sometimes, so they are often backwards (pull on style). Whatevs.

She usually chooses from a few options I set out, but if she's being particular or we aren't in a big rush, I let her choose. She wore bike shorts, a tutu, and four tshirts the other day. And yesterday a denim mini skirt, a tshirt, baseball cap and rubber boots.

@catomd00: this is my philosophy too. Although, DD often wants to wear a dress and a skirt and pants, all at the same time, so I kind of have to reorient her choices.

At almost two I still choose her clothes, for the most part, but I do give her choices between different tops, for example. Now that it's warming up I may let her have a little more control over her wardrobe.

O & E need to hangout! haha E is totally into wearing what SHE wants. It's usually a dress with leggings, and we fight over inappropriate shoes (winter boots when it's 80 or sandals when it's snowing.) She's vey opinionated and I usually go with it unless we are going somewhere nice and I need to make sure she's dressed appropriate and I give her 2 options.

Most of the time he can't be bothered to choose, but if he expresses a preference, I go with it. He's at least as good as DH at matching.