Tomboy Jo

There's an age-old adage, "There's more than one way to skin a cat" and that is very true when it comes into many aspects connected with age regression and the life that goes with it so I usually counsel an acceptance that there's no one magically right way to go about it.
This is especially true on the little/middle girl side where sometimes it might seem we're all frilly dresses with lashings of lace but there was a girl, very famous one who was a heroine of mine who went a whole 180 degrees the other way

 "George" from the Famous Five series actually was Georgina a girl who was very much a Tomboy, taking the lead and liking to wear less feminine girls attire to the point she did wear schoolboys shorts (although most modern versions remove this essential aspect of the storylines).
You could say she was rebelling about gender roles  and what was seen as suitable attire for girls and actually there is a fair bit of her in me that does wear shorts that aren't super pink and with curvy piping outside of my love of dresses.

I do wear the above navy tailored 'boys' shorts with my girls attire as that girl which is at times more practical and yet also does tie in with liking to present as a middle/little

l also have this black pair bought from a famous school wear supplier in the UK who does stock them in wide range of sizes. They do look very smart on me with nothing looking  too tight and the side pockets are helpful.
They aren't the sort of traditional grey lined shorts of yore having more in common with longer cargo type shorts but being more formal and made from stain resistant teflon like most school skirts and trousers are.
This while not necessary pleasing traditionalists who want them al a Angus Young this does mean it is possible to wear them amongst the 'muggles' with socks that don't scream out 'adult schoolchild' on the prowl as indeed I do in my neighbourhood with no one batting an eyelid.
This Saturday for instance I wore them with my Hello Kitty long sleeve t shirt and white frilly ankle socks outdoors walking as it was fairly warm for time of year which is pretty Tomboy.