Prologue
Harry James Potter was in his fourth year of Hogwarts when he found out a side about himself, he liked dresses, skirts, makeup, etc. Now, he was in his sixth year and that side of himself only expanded. Only this time, he finds out that his feminine side came with way more than just short skirts and stockings.
Harry Potter was a fairly simple person, besides the fact that his parents are some sort of legendary heroes. He was a small percentage of the soul of the one who shan't be named. Nearly everyone in the entire wizarding world knew his name and dubbed him The Boy Who Lived. But, besides that, Harry had minimal hobbies like reading, drawing, ice skating surprisingly, and sometimes singing.
Outside of being a wizard, he was what could be considered normal, well as normal as someone who can speak to snakes can get. The only thing Harry would dub himself as not exactly normal was the fact that he loved wearing girly clothing. (it wasn't that he thought that clothes had a gender, rather it was how it was yet socially accepted by either society yet) Despite that, Harry had no reason to hide, and nor did he hide the fact that he wore feminine clothing.
Quite the opposite, he would normally wear the articles of clothing around the Griffindor dorm and common room. It's just that he couldn't wear the clothes outside of the dorm due to the school's dress code. When he first started wearing the clothing it was a skirt here and there or a pair of shorts and thigh highs, or a scarce occurrence of a croptop. Harry liked to sit in front of the fireplace with a book in his hand while he wore the occasional skirt or croptop.
His dormmates had questions, of course, and so did his own mates. Hermione was the first to acknowledge it and the first to accept it. The Weasly Twins came after Hermione, George liked to wear light makeup and chokers so he could understand Harry. Fred explained to Harry what being androgynous meant, the twins helped Harry with finding himself. Ron took a bit of work, having to explain that clothing didn't have a gender and that anyone could wear what they wanted.
Whilst Harry found himself, the Weasly brothers found themselves too. George was pangender, Fred was genderfluid and Ron doesn't want a label but preferred to be seen as a demiboy. Harry soon after came out to his friends as genderfluid, he believed it fit him due to his androgynous features. Hermione of course, fully supported this, as she was a male assigned at birth but after a while, found herself coming out as trans.
But, alas, gossip spreads in the wizarding world and our lovely Griffindors find out just where they stand in the world's eyes.