This is a hard one for me.
I want to say, "Hell YES."
But I wonder... is that only because DS has never expressed an interest? I don't count "dress up" clothes as a dress (even princess or fairy or playsilk skirts or whatever) because that is pretend. But if I was going to take DS to get his picture taken and had picked out his shorts, polo & sweater vest and he said, "No I want to wear this dress instead" could I *actually* suck it up and say, "Great" or would I waffle, make excuses?
I did recently realize that although he reports his favorite colors as "Red, pink and purple" I buy the vast majority of his clothes in... blue. So I asked him "DS would you like a pink shirt" and then went to Old Navy yesterday and got him a pink polo. He really likes it, but not more than any other shirt (and, btw, that is the *only* color polo they have left--- the blue, yellow, etc... are long gone).
He wears nail polish w/impunity. He chooses his own hair (wears a small pony on top of his head many days, is in the process of growing it out). He wore a pink leotard to gymnastics. But I *do* encourage him to wear swim trunks (he HAS worn a girls swimsuit before, though).
I *think* that I would be great w/DS wearing a skirt/dress to something "normal" (preschool, shopping, etc...). Less so for pictures, special holiday function, etc... BUT this is something that really disappoints me about myself and I work against. I would *LOVE* DS to wear a kilt and am searching for one--- if anyone has an idea where to get a 3T kilt for cheapish please let me know. But a dress?
I guess one major issue is that I just don't like kids in dresses much. When DD was DS's age I had her wear pants to family functions (holidays & such). Now she is older and generally chooses to "dress up."
I would have no issue with an older boy wearing a dress or skirt. I would explain that some (rude, ignorant) people may have an issue with it but that it was his choice and *I* would support it. I guess I also just get sick of being "that freak"
and it seems like one more battle that doesn't *seem* important to DS.
Okay, I guess I answered my own question. If it was important to DS? Yes. Am I going to go buy him dresses like I buy him other clothing without him requesting it? No.
Except a kilt. Because that would be just TOOOOO cute.