(Cue eye roll). Listen, you can roll your eyes all you want, but the fact is that I am a FULL supporter of dressing my kids in matching clothing for certain occasions. Let me elaborate: See, the thing is- it is for sure cute (IMO)…
BUT for us it serves a MUCH more important purpose: Safety. Really. When we are in public places such as birthday parties, etc, I like to dress the boys in matching shirts so that we can quickly survey an area to find all three quickly. I believe we are able to do it FAR faster when they are ALL wearing the same shirt and we don’t have to try to remember what they were wearing. Not to get real serious here, but they always ask what a child is wearing if you (G-d Forbid) can’t find them (in a store, etc.-This, btw, has thankfully never happened to me, but I have witnessed it and it is scary!)

Chuck E Cheese

Rehoboth Boardwalk

DiggerLand

Disney World

3 Bears Park Festival
Now, we of COURSE have the boys wear what they want MOST of the time (save for the examples I listed above). I think it is super important for them to have autonomy and independence in what they wear (to an extent and again, MOST of the times).
I also want them, though, to be flexible in terms of wearing what we need them to wear- in fact, they LOVE matching! They always looks at each other’s shirt like “that’s my shirt!”
So. There’s my story. What’s yours? Do you do “matchy-matchy?”