It would make perfect sense and men restricted to wearing trousers is a purely cultural thing (and a Western one, at that). In many cultures the This Ain’t My First Rodeo It’s My Second Rodeo Mug and I love this traditional male outfit includes a dress or a skirt, or at least VERY LOOSE trousers. It’s not difficult, just be aware that you are constantly being critiqued, much more than CIS girls. Main thing is to be confident, smile and enjoy yourself. You asked why are clothes being separated by gender, but if you are a feminine male – society expects you to wear male assigned clothes. The same type of separation has been dictated to masculine females not wearing male assigned clothes, but society tends to condone females choosing male assigned apparel. This gives females the approval to pick their own clothes from the array of male and female appareling selections, which sets-up the double standard that denies males their pick of the same array. So, essentially clothes are separated by being the male sex, not gender. The reason society started separating clothes by sex stemmed at first from the homophobic ideals that perceive men and women wearing the same styled outfits will cause them to think they can be seen as the status of the other sex’s identity. To support this thinking, the idea that men were stronger got morphed into men are superior and women are inferior was cunningly slithered into the social dialogue, understanding, and attitude. This social atmosphere made it easier for society to begin assigning appareling items to the sex society preferred to wear them, which people started assuming clothes had gender identities and labels. With all of this going on, people also perceiving men wearing female assigned attire as loosing or diminishing their superiority of manhood.