Parts of the past are always going to be uncomfortable, not following any "approved" script, trope and may be a bit removed from where you are now even if in some ways you'd of never of got there otherwise.
Anything around gender expression, by which I mean how you may express your sense of gender by how your dress has the complication you may well be deviating from a path established for you.
In my era especially it was unheard of for a boy to ask for or even be asked how and what he'd like to wear.
He was dressed in what his family thought was most suited to him and that was that so if like me you did wish to explore other more feminine presentations this did involve raiding female members closets and any clothes for donation for suitable things.
Wearing someone else's underwear without permission is shameful but we were not offered the chance to try any on and have them bought for us to wear and look after.
We could be and I was caught out where outcomes could vary from a severe scolding to acceptance of variance which in time occurred with me.I learned and she learned to accept my feminine boyhood buying underwear for me.
I feel boys like that are best supported to explore what makes them the most happiest and comfortable being themselves be they more "girly" all the time or a mixture of traditional boys and girls styles.
The more I think about it, the more I feel at least for someone like me formal adulthood as a status was a mistake because I don't have what it needs to handle it, I mean I scarcely coped with adolescence requiring sheltering from some everyday teen situations as I just couldn't 'read' them and look after myself.
I felt very much like a fish out of water then and it certainly hasn't improved in years either.
I so want it revoking and a parent figure looking after me instead.