I am not now, nor have I ever been, a trendy dresser. I am pretty much a jeans and t-shirt/tank type of gal. I do own a couple of dresses and skirts now, but was a major tomboy all through school. So I guess I am not doing a great job of passing on any sort of fashion sense to my kids, but I am totally OK with that. I am happy that they don't need the name brand clothes and shoes and generally don't care what they wear. But kids can be pretty funny when they just start to dress themselves.

Right now, my youngest is 2 1/2 and just started dressing himself on an occasional basis. Today was one of those days.

He put on his SpiderMan t-shirt, Batman boxers (as shorts with undies underneath) sandals, sunglasses and winter hat. Talk about a well dresses little dude! Totally adorable if I may say so in my (unbiased) opinion.

So, did he leave the house this way? You may ask. Call me an awful mother if you must ... but, yes, he did. We went to my sister's house (which doesn't necessarily count), but then also went out to eat with the inlaws at a very relaxed pizza place (he didn't have the hat on for that though). Thing is, I am kind of torn on this whole thing sometimes. Obviously, a 2 year old is going to come up with some crazy combinations when you let them dress themselves and some of them are going to be rather inappropriate. But even with my 5 and 9 year olds, there are times I look at them and think 'What in the world were you thinking when you put together THAT outfit?'. But how much control should we really have over what our kids wear.

At least for now, I am the one buying most of their clothes so that makes it easy to weed out inappropriate attire that I flat out won't let them wear. I give them certain instructions as to what type of clothes they need to wear (i.e. shorts and a tank top in December in Wisconsin just doesn't work). And there are times, like church, that they know they need to wear some of their nicer clothes (though our church is not a suit and tie type of one or anything - just the jeans without holes or khakis and a nice shirt will do). But beyond that, how far should we go? Do I make them change - or even suggest they do - if their clothes just don't match? Do I stop my 5 year old from trying to come up with and outfit that looks like (pick superhero/nintendo character for the day) while he is getting dressed so he doesn't end up looking a bit crazy (and wearing a cape to the grocery store)? Or do I just praise them for actually being fully dressed without me having to fight them about it (since my boys would much prefer to spend the day in their underwear ... and a cape)? And how much do the rules differ if you are going out in public compared to when you are staying home? Do you make them change because you are a bit embarrassed by the fact that your 9 year old still doesn't understand that blue and yellow striped pants really don't match the green and red striped shirt just because they both have stripes? Or do you let them go as is and suck it up?

Lots of questions and I don't really have any answers. There are times that I really want to tell them they should change and I do, but then end up feeling kind of guilty for it. Then, there are times that I take a kid out to eat in a t-shirt and boxers. How much control do you exercise over what your kids wear?