5yo GS is princess obsessed, and loves to dress up when he has the opportunity, but doesn’t own any princess dresses because of parents discomfort. If I bring him to Akershus or 1900Park will there be tons of girls in costumes? I think he’ll be jealous, so I’m thinking of borrowing a Rapunzel dress for him to wear that night. Will he get lots of strange looks, or is this becoming more mainstream? Fwiw, he won’t be mistaken for a girl, no matter what.
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Personally I say if wearing it makes him happy, let him!!
And YOU are an AWESOME grandmother for supporting him!!!
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He might get strange looks, just as a big kid in a stroller might get strange looks. Chances are he won’t even notice at that age though. If it makes him happy, go for it.
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I bought a woman’s handbag decorated with Minnie Mouse to carry with me while I was at WDW. I bought it because it was perfect for my needs and because — damnit! — I liked how it looked.
I felt utterly unself-conscious carrying it around because, well, it’s Disney World, which is surely one of the safest places in the world.
I wasn’t aware that I was getting funny looks from anyone, and the saleswoman at the store on Main Street where I bought it was delighted with me making the purchase.
So if your grandson wants to wear a princess dress, then good for him. It’s 2017. People can be who they want to be, especially at Disney World. And I think it’s terrific that you’re facilitating this. Good for you!
(PS I gave it to my friend after our trip. I’m not confident to carry the bag round my home town!)
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I love that bag!
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I love that bag too!
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Maybe the only question should be whether his parents will be upset if you do this. Make sure to get their blessing.
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Go for it, who cares? But I agree, I’d run it by his parents first. As a parent to two young children I always want a clue of what the grandparents are doing 
But, my DD7 loves wearing princess dresses and pirate outfits and my DS4 is planning on wearing a prince charming outfit when he goes to CRT but an elsa dress when he meets Elsa WDW is all a place of fantasy and make believe, why not
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My suggestion (since parents are a little uncomfortable) would have him pick out a princess shirt in the girls section of Target. Then if you take him to one of the character dining bring a complimentary tutu “if” he wants to wear it once he sees others.
I would consult the parents.
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Let him do what makes him happy. Get him the dress. 
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I saw a couple of little boys happily wearing princess dresses when I was at WDW in October. I have no doubt that cast members will make him feel more than welcome and included.
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I am all for people being being who they are - however - if the parents are not comfortable with it - you really need to honor their wishes - sorry you are stepping over the line IMHO. If they are ok with it - then go for it - but if not - you should not. The issue in this case is the wishes of the parents.
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You mention he doesn’t own any princess dresses because of parents discomfort
I will be honest if my parents had taken our son to disney and dressed him as a princess I would be thinking they’ve lost the plot a bit? And it wouldn’t be a photo I would be putting on display! Lol
Although years later it might be something to look back at and laugh at
If he likes dressing up then why not a Prince outfit. I’m sure they are pretty flamboyant and bright?
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I disagree, I think that what the child wants should be a priority, as long as it’s nothing unsafe etc. He has rights of his own, he is not an extension of his parents. Why should he miss out on what he wants? It’s just an article of clothing, she isn’t suggesting tattooing him or cutting his hair.
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I respectfully disagree. Parents are in charge unless THEY are the ones doing something unsafe. THEY are the ones responsible for the day to day care, feeding and emotional growth of their child.
If I had asked my parents not to get a specific toy for my child and they did - I would be very upset with them.
Sorry the first priority is respecting the wishes of the parents - unless you plan to take over ALL parenting responsibilities. This is very unfair of you to interject YOUR wants onto your grandchild at the KNOWN discomfort of your own child.
I don’t think anyone on this forum has any concerns, issues or prejudice against this boy wearing a dress and that is great - but we are not the ones caring for this child. There is a larger family dynamic here - and you have to respect how the parents deal with it in their own way
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I see your points, I just don’t agree. But at the end of the day, it’s OP’s decision and she only asked for advice on whether he would get strange looks.
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I once again respectfully disagree. At the end of the day it is the PARENT’s decision 100%. The fact that it is noted that this child doesn’t own any dresses and that discloses that the parents are uncomfortable with this clearly illustrates that she knows she is going against the direct wishes of the parents and is looking for validity in this decision.
Once again - I personally have no issues, concerns etc with this - but clearly the parents do and unless we are willing to take on responsibilities for the child - no one has ANY RIGHT to override their wishes. NONE. This is not a question about wearing dresses or not - it is a question of “should I undermine how my child is raising their child”
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Sorry, I meant it’s her decision whether to do it against parents wishes, not ours.
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Understood. However no - SHE doesn’t have the right at all either . NONE. It is 100% the parent’s decision. End of story. If she wants to do this - she MUST get consent from the parents.