Again, hugs to you!!
I think this may be a fantastic teachable moment for your daughter - you seem to be handling it wonderfully so far!
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When I was very young — maybe four or five — my aunt bought me a cowboy outfit for Christmas. I think it was a really expensive one. My mother made me put it on straight away and all I remember (there’s a photo to back this up) is crying my eyes out because I really didin’t want to wear it.
I don’t know what that meant — I didn’t grow up to be an adult male who enjoys wearing stereotypically female clothes — but I do think I must have hated being made to be something I wasn’t.
Since my earlier posting, there’ve been a lot of pretty strong posts saying that this is all about the mother. I do respect that view. Equally, if the young lad really wants to wear a princess outfit — and you’re very clear that that is his freely chosen preference — then a conversation with the mother seems appropriate.
It won’t turn him gay, any more than being made to wear a cowboy outfit turned me straight.
It feels — here in the UK, at least — that society is moving remarkably fast when it comes to gender and sexuality. Despite being gay, I’ve not generally been particularly open to the idea of gender fluidity, yet I’ve recently found myself questioning why I’m asked my gender when I fill out forms on the internet. “Why do you want to know?” I think to myself. “What difference does it make?” Sometimes it’s relevant, sometimes not.
Childhood should be about fun and fantasy — especially at Disney World. If this young man wants to dress like a princess and you can find a way to make his mother be comfortable with that, then I’m all in favour. Let him be who he wants to be at that moment.
You know, funnily enough, I bought my “ladies” bag right after I’d watched HEA. I was actually genuinely moved by the message. And when I saw that bag, I thought “I really like this — it looks good and it’s exactly what I need to carry for this trip”. The assistant in the shop — and my friend — made the whole thing so much fun and so comfortable.
Of course I’m back carrying my manly rucksack now, but it was fun while it lasted — and a nice memory of many of my trip.
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I’ve just remembered. When I was a young teenager I had some pocket money and I went shopping to spend it. I found some really pretty notepaper — it had flowers on it, but I thought it was classy and would be great for writing letters.
When I brought it home my father saw it and he was very angry. He made me feel so ashamed that threw the paper in the bin.
That was over 30 years ago. And I remember it like a video recording in my head.
Kids remember stuff. Maybe not five years olds. But older kids do. Sometimes for a lifetime.
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When I was at Akershus last Nov and CRT in June, DD and I were so focused on what we were wearing and doing that we didn’t notice what others were wearing. But I can tell you that we were not wearing princess gear and didn’t feel out of place.
I don’t think it’s mainstream, but I’m not an authority on that. However, I think this falls in the same “concern realm” as people being nervous about being in Disney alone. Most/many are worried that looks from other guests as they make the realization that they are in the parks alone, could impact their good time.
Well I have good news for ya: everyone is so busy with their own vacation, the chances of them noticing you and yours is EXTREMELY slim (unless of course you’re actively making your presence known to them, like constantly screaming or perhaps a rousing game of “stop hitting yourself” for all to see 
). For something so innocuous as a 5 year old wearing a princess dress, I think the possibility of anyone caring or even staring is next to 0. Heck, you could probably do the whole Bibbity Bobbidy Boutique deal and still no one would notice or even say anything. Disney World is such a mass of people that you almost need to make an effort to be noticed, and I rrrrreally don’t think a dress is going to cut it. And if your grandson is well behaved and doesn’t need to be the center of attention, you have even less to worry about.
Also, don’t forget, people (when not on the internet) are far more polite and far less quick to call out anything they deem “unacceptable.”
/PS, you guys on this forum are awesome. Like the immediate concerns for this only focused on the impact of possible parental disapproval of act rather than social perception. Seriously, we have come such a long way as society. You rock.
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This headline was on the front page of a UK newspaper this morning.
Here’s a link to the story (from a different newspaper): Let boys wear tutus and high heels if they want to, Church of England says
It’s worth a read.
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Maybe take him to one meal and gauge his reaction first? When I was young I played with Care Bears while other boys had GI Joes’, wore girls clothing because pink was my favorite color and my parents could only find girls clothing in pink, and loved Disney Princesses. However, the one time my mom put me in a dress as a joke, I felt so uncomfortable I started crying. My dad got pretty mad at her. It is still the one and only time I’ve been in a dress. So I know from my own personal experience that just because a boy might like certain things, he might not like being in a dress.
Thank you for sending the article! Forwarded straight to my daughter.
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Point taken about the possibility that he might be embarrassed about being in a dress in such a public place. I’m planning to bring a change of clothes in any event. However, he heads straight for the dresses as soon as we arrive at a “play place” and he wears a dress almost the entire time we’re there… It’s a hoot to watch him lift his skirt to get up the monkey bars. 
He’s never gotten a mean comment there… Adults often smile as he goes by.
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I am with everyone else and I don’t think you’ll have any issues. But I would also be prepared in case you get that one ignorant person who feels the need to say something loud enough that your grandson can overhear. DS has a medical condition that causes him to fatigue more quickly than the average child. We ended up using the stroller longer than most probably would (and while he’s average height, he’s very skinny, he mostly fit into it longer). But he absolutely didn’t want a wheelchair. You would think folks would see me pushing it with my two massive leg braces and figure out something might not be right with either me or him, but there were a few comments about the ‘kid who was too old for a stroller’ who I’m sure thought they were being quiet enough I wouldn’t hear them (or maybe not). Anyway, DS and I talked about how some people are rude and inconsiderate and this is why you shouldn’t make snap judgments. Was a nice teaching moment. But have something prepared so the poor little guy doesn’t get hurt by the experience - because he absolutely should be having the time of his life.
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It is not mainstream for boys to wear dresses by any stretch. He will stick out like a sore thumb, and will probably get some looks of disgust (Just being honest). Most will probably just think it’s funny. And honestly most people wont even notice period, because they will be focused on their own kids. If anything he will probably get looks and made fun of from other boys and girls his age. I’m surprised a 5 year old boy would want to dress up as a princess.
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If you’re surprised that there are boys who want to wear princess dresses, you haven’t been paying attention. It might not be common, but it’s not all that unusual either. BTW, since this thread is now resurrected… his mother has said that if it will make him happy to be a princess in a princess parade at Disney, she’s okay with it. I’ll obviously have to talk to him about the potential for people to be cruel. Sad that anyone would be disgusted by a child pretending to be a princess.
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My son loves the princesses (LOVES them), too, so I can relate. He will play dress up at home in a princess dress with a light saber and a Mickey Mouse hat… he just knows that he loves the characters. And, as he pointed out to me, Elsa is the one with the cool power.
With that said, the past two Halloweens he was Beast and then Gaston. Granted, these aren’t easy to find so I ended up making my own, but we dressed our baby up as Belle and he was thrilled. Had he really insisted on being Belle or Elsa, we would have gone with it, but this theme worked for him. If the parents aren’t on board with a dress, I would see what Princes I could find because those pictures will be awesome, and the princesses will definitely play up to it. Maybe offer to bring a rose or snowball or something for photos with his favorite Princess?
If you or anyone you know sews, you can take an adult princess shirt and make it a little less pink and flouncy. Even for my daughter I would prefer a lot less pink and fluffy.
Like someone above said, they need to work on boy options based on the big movies - not just Star Wars, sports, or villians.
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He is FIVE!!! Let him have the fun he wants. If someone makes a point to make him or you feel uncomfortable, keep in mind they are wasting time when they could be experiencing real magic. But as stated above, I would not hide it from his parents.
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How is it imposing her beliefs and wants on a child? He wants to wear a dress, she wants to make him happy. I doubt very much she has a burning desire to force him to wear a dress against his will.
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The notion that I would push my GS to wear a dress is seriously laughable. As for “putting him out there for ‘people to be cruel’” … the corollary is that if I don’t allow him to be who he is, in order to avoid the cruelty of strangers, then I’m the one inflicting the pain. The emotional distress is unavoidable – either he feels the distress because he wants something desperately and the people he loves and trusts tell him he can’t have it because he’s a boy, or he feels the distress because strangers are thoughtless, mean-spirited, ignorant, or whatever. He’s going to face the latter in his life no matter what.
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I cannot actually believe what I’ve just read. I can’t say anymore.
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Maybe I came from a different time and era. This to me is a non subject at his age. Homophobia seems to be playing some type of role here and it shouldn’t. I played with dolls as a child and my sister played with soldiers at that age. We were country bunkins and we had our fun doing things that today people would skuff at. Parents, do what you believe is right because this is your child and anyone else’s opinion is a non issue at this stage in his life.
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And that’s why I said nothing more than I did.
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