One possible plotline could be Harry exploring his identity through fashion and makeup. He might start a fashion club at school where he helps others express themselves too. This could lead to him facing some initial resistance but eventually winning over his peers with his confidence and creativity.
In a fanfiction, Harry could be magically transported to a world where wearing dresses and makeup is a norm for everyone. He then has to navigate this new world while also learning more about his own relationship with these things. Maybe he discovers new magical makeup that gives special powers and he uses it to save the day.
Another plot could involve Harry using his love for dresses and makeup to break gender norms in the wizarding world. He could team up with Hermione to start a movement for more inclusive fashion in Hogwarts. Along the way, he faces challenges from traditionalists but also gains many supporters who see the beauty in his unique style.
Luna would absolutely love it. She would probably join Harry in wearing unique dresses and trying out new makeup looks. She might even introduce Harry to some magical fashion items that she has discovered. Harry's friends from the DA would also be mostly supportive, seeing it as a form of self - expression and a way for Harry to break free from the traditional wizarding world's expectations.
One idea could be that Harry discovers a magical dress in the Room of Requirement that gives him special powers. Another could be that he wears a dress as part of a disguise to infiltrate a wizarding event. Or perhaps he is cursed to only be able to wear dresses for a period of time and has to deal with the reactions of his friends and foes alike.
It could also be part of an experiment. He might be curious about how it feels to wear different types of clothing. Or perhaps he's been influenced by some new magical culture he's learned about that has different views on clothing and gender. There could be a spell or a potion that makes him more in touch with his feminine side, and as a result, he starts wearing dresses.
One possible plotline could be that it's for a school play at Hogwarts. Harry is forced to wear a skirt as part of a cross - dressing role in a wizarding drama. His friends initially laugh but then come to support him when he faces some bullying from the Slytherins over it.
One story could be about a boy who wore makeup and a dress for a school play. He initially felt nervous but as he got into character, he gained confidence. The makeup and dress helped him transform into the role and he received a lot of praise for his performance.
There could be many stories. Maybe it's about a boy who is exploring his gender identity and finds freedom and self - expression in wearing dresses. It could also be for a school play or a costume event where he has to wear a dress.
Maybe Harry could be on the run from some dark wizards and he disguises himself as a goth girl to avoid detection. He would have to learn how to act and move like a goth girl too, which could lead to some comical situations.
Maybe it's for a school play at Hogwarts. Harry is chosen to play a female character and has to wear a dress. His friends Ron and Hermione have different reactions. Ron might tease him at first but then support him when he sees how serious Harry is about doing well in the play. Hermione, on the other hand, helps him with his lines and how to act in the dress.
He might feel confident. Makeup can enhance one's features, and he could be enjoying the new look it gives him.
There was a crossdresser who found a beautiful black dress at a thrift store. The black dress was a vintage piece with lace details. He decided to wear it for a photoshoot. During the photoshoot, he told stories of how crossdressing made him feel more in touch with his feminine side and the black dress was like a symbol of that exploration. It was a liberating experience for him.