A few month ago, I asked: Can I avoid nice clothing being a source of argument? That was mainly focused on my eight year old, and now I have a related question... but about a preschooler.
Our youngest (three and a half) only wants to wear about five shirts, all t-shirts with dogs on them. Any other t-shirts (e.g. dinosaurs, trains) are rejected as "too fancy"* and are only worn after a lot of arguing or negotiating. An actually "fancy" shirt (with a collar, either polo or button-down) is rejected and leads to incredible tantrums if we try to push the issue; I once suggested he could wear a tie and he nearly exploded.
Since he's a preschooler, this has not yet been a major problem: we don't go many "fancy" places anyway, and there are different standards for acceptable clothing for young kids in a lot of situations. But, he's been asked to be the ring bearer in my cousin's wedding. If we accept, the event is going to require a suit.
I have no idea how to get him interested in the idea of dressier clothing. We have two months to prepare: what can I try to make him more open to different, "fancy" clothes?
* I feel it's important to note that neither parent defined these shirts as fancy: it's an adjective that he decides how and when to use, and we have a tough time predicting when it will be an issue. (I would not, on my own, decide that a bicycle t-shirt is fancier than a doggy t-shirt.) I'm also unclear on why fancy is a bad thing, but that's the implication he makes.