Too old to play dress up?

[trybest]

My DS (9, turning 10 later this year) used to love playing dress up with his sister. Their dress up box was full of items and costumes from disney, superheroes, animals to princesses and pirates. He lost interest around the age of 8 but just recently he got the box out again and realised most of the outfits no longer fit.
A few days ago he came to me looking a bit uncomfortable, and asked if I could buy him a princess dress he had seen online. He clearly felt unsure about asking.
I don’t have any issue with him wanting to wear a dress. When they were younger, both kids swapped costumes all the time and both DH and I were totally fine with it. Last winter he wore tights under his school trousers and I backed him, even though a few mum friends raised eyebrows and pointed out that it was more of a girls' thing.
The dress he wants isn’t cheap and I do worry it might only be worn once or twice before it’s forgotten. But at the same time, I’d feel awful saying no when he’s finally found the courage to ask.

AIBU?

When’s his birthday?

In October

I would say no because it’s not his birthday, if he still wants it in September revisit the situation

Unless he has pocket money saved I’d probably say that he can have it for his birthday. I’d probably look for something cheaper from Facebook / eBay and suggest that too.

It's just fabric of course. Am sure you'll find same or similar on vinted!

I’d buy it for him if you could afford it. He was brave to ask. You can always return it if he’s not using it.

id answer the same for either of my children (boy and girl) and head straight to vinted. I never pay full price for things they won’t wear regularly.

I don't know which way the aibu goes, but I'd wait for birthday or Christmas not because he's a boy and it's a dress, but because it's expensive and kind of a "toy" in that it's not really essential. I'd be the same for my daughter the same age.

Get one from Vinted.

I'd be rewarding the bravery and the strength of character to know and share that he wants and not just follow the crowd. Also, this will be an invaluable moment for you son to know he came to you with something that was important and possibly a worry for him and you fully accepted him and supported him. Invaluable.
Could look on vinted and see what is avaliable, let him look through the options and see if anything catches his eye.

What on earth is he doing browsing unsupervised online?

The reason for saying no is the fact it's too expensive to be worn once or twice & it's not your birthday! But maybe he could use his own money to get something off vinted?

My DS (11) loves dressing up too, but has now channelled it into sports kits & alllll the accessories. Be proud that your boy feels safe to tell you what he really wants, despite knowing it's outside the norm for a 9yo boy.

Denying it just makes it appear wrong and could force him to box himself off in an arbitrary boy/girl category - it's not wrong to be a boy who likes colour, beautiful materials & sparkles, it is just a shame our boys are often restricted to the borefest of navy, grey and maroon - a splash of khaki for summer vibes.

We’ve blocked adult content on the iPad, but I can’t block every single online shop. He was just looking at dress-up costumes for children.

Never too old for dressing up, did you not see the met gala coverage last week? Plenty of men work in fashion too.

I'd buy it for him. We express ourselves through what we wear and this outfit might allow him to show a part of himself he otherwise has to keep hidden. It's so important to feel valued, and he came to you and asked, which shows he feels safe in your kindness and understanding as his parent.

Definitely don't say no. He's been so brave to ask. Let him express himself 😊

Life’s too short, buy the dress. Get one from Vinted for a few quid. It was brave of him to feel comfortable enough to ask you.

Vinted or charity shop. He can have dressing up costumes but you don't have to buy a specific expensive one.
But I agree with pp, he's too young to be browsing the internet like that.

Knowing he was hesitant to ask would tell me he needs to trust you and needs to know you'll support him. Buy the dress and he'll know you respect him.

A former neighbour had a boy who was always in princess dresses and sparkly things. He is now in his 20s, is a very flamboyant dresser and very comfortable with being gay. His mum says that whether he had been straight or gay, they were so glad they supported his clothing choices right from toddlerhood.

Let him have a dress and be a kid for that bit longer.
Your never to old to play dress up never to old to play with toys either.
Im 38 and still have coloring books and plushies also have 3 barbies im not ill im not nuts but why not.