• the reason he wears a hat all the time is when he was like 9 and started realizing he wasn’t a girl, his parents wouldn’t let him cut his hair short but they would let him buy the star hat. so he put his hair up in it and wore it all the time. when he turned 11 or 12, they let him cut his hair short, but he kept the hat bc he was so used to having it on his head.
• and like what if his parents didn’t ever let him cut his hair? or really accept that he wasn’t a girl? and then on the bus in the middle of the trip to gravity falls he just got up and muttered something like “nope, i can’t stand this anymore” and got up and headed for the lavatory at the back of the bus. and Mabel jumped up after him and started banging on the door and yelling bc what if he’d done something really horrible?? but then he just opens the door with kiddie scissors in his hand (from mabel’s Craft Suitcase) and his hair is all weird and messy but it’s //short// and he’s grinning kinda and “sorry i scared you mabel. there was just no way i was gonna meet people i’ll be spending the summer with while i had long hair.” And that’s why his hair is so messy
• in the previous scenario i mentioned, dipper buys his binders from the same site mabel buys her sweaters from, so the parents don’t really bother to check through pages and pages of receipts that say things like “MEOW WOW MID-PURPLE BEDAZZLED SIZE M” for Trans Activity
• stan somehow doesn’t?? know??? enough abt his grandchildren to know that dipper is trans? which is why he gives dipdop the whole pituitary gland talk. like he’s been so out of touch that he hasn’t had much knowledge about dip and mabel before now so he’s just like ‘hi dipper hi mabel!’ when they step off the bus and calls dip by he pronouns and dipper is so relieved
• mabel reads everything she can get her hands on about binder safety and being respectful on pronouns and stuff like that when dipper comes out to her, and she sticks bedazzled post-it notes that say things like ‘remember to cough!’ and stickers that have like 'UR A RAD DUDE’ on them in neon bubble letters, in places dipper will see them
• she swears to dipper that if their parents kick him out, she’s packing up and leaving with him.
ok but let’s think about when Dipper first starts his transition, he cuts his hair and stops wearing feminine clothing, but he worries that he still looks too much like a girl, too much like his twin sister, especially if she’s just wearing a plain shirt and pants and puts her hair up and they just end up looking identical again. So one day he blurts out to Mabel that he worries that no one will ever take him for a boy because they look too much alike, and Mabel’s like “oh don’t you worry bro, I’m gonna embrace the crap outta my femininity, so that everyone can tell that you’re my brother” and she busts out the glitter and the bedazzler and she gets to work modifying her sweaters to be as girly as possible and she grows her hair out and always wears cute bows and hairbands and sure enough, no one has any trouble discerning which of the two Pines is the brother and which is the sister