This is another article that is fairly centered on the topic of femboys, but some of their arguments could be more generally applied to the question of why wearing gender-non-conforming clothing is becoming more popular online.
In many ways, Alex is a typical man who just so happens to enjoy wearing skirts and high heels. He is married to a wonderful, supportive wife and has a young son. His hobbies include reading, programming, metal music, playing instruments, video games, cars, hiking and a number of other smaller things.