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Is It Normal For My Brother To Wear Skirts To School? And If So He Need A Couple Pictures Of Some?

If you define normal as the socially accepted standard of behavior for males in his age and situation, probably not. If you define normal as acceptable due to a lack of innate harm, probably. If you define normal as his standard practice, you’d be a better judge than I would. If you define normal as “a good idea,” that depends where you live and what kind of school you go to—if he’s going to be bullied so much that he becomes depressed and self-mutilating, it’s probably not a good idea. Ultimately, questions about “normal” are really hard to answer, because “normal” is a really hard word to define precisely.
If your brother simply likes skirts, and he still considers himself a male, then he’s at least an occasional cross-dresser. Personally, I have no issues with that. He just likes “girl” clothes. That’s no different than girls who like “guy” clothes, and the only reason people think it’s so shocking is because they’re still slightly sexist, and thus impose rules on men that aren’t imposed on women out of the belief (whether acknowledged or otherwise) that men are superior to women, and manhood or masculinity, once obtained, should not be rejected or substituted for something more feminine. This is absolutely ridiculous. The genders are innately different, but to presume that one is superior to the other involves denying a huge body of evidence regarding the varying degrees of usefulness of various traits and tendencies in certain situations. If your brother wants to wear a skirt, for heaven’s sakes, he should be allowed to wear a skirt. You’d let your sister wear pants.
If your brother, however, does not actually identify as male, and would prefer that you think of him as your sister, I will respectfully alter my verbiage to reflect this and begin to call “him” a “her.” She, then, is transsexual. This will probably require you to spend a little more time in thought and demand more acceptance of you. Transsexual girls are at a particularly high risk for depression and suicide, in large part because of the very reason that men are not allowed to wear skirts. For what society deems a “man” to announce that she’d rather be a deemed a “woman” is, to many, absolutely unacceptable, and this social ostracism can cause her a lot of pain and distress. If your brother is indeed your sister, she will need your love and understanding now more than ever. She also may need your protection, because in many cases, transsexuals are bullied rather intensely, but may not have the self-esteem and confidence to stand up for themselves—after all, all of society has been pressuring them to be something they’re not, and telling them they’re inferior to everyone else since more or less the day they were born.
If your sibling (withholding gender to respect my lack of knowledge on the subject) is likely to suffer harm—whether physical or emotional—as a result of wearing clothes that don’t conform to the socially-assigned gender s/he belongs to, I would advise you to try to help your sibling find other ways to make him/herself more comfortable than dressing as him/herself at school. This is rough. I know because I’ve been there. However, it would be better for you two to keep it toned down at school and avoid the threat of violence while allowing him/her to be him/herself at home and in other settings than to try to force your way into school in clothes that fully suit his/her identity and expression preferences and risk one or both of you getting hurt.
I don’t see why the pictures are necessary. If s/he wants a skirt, just go buy one. It works better than way anyway.