Back in the day, we viewed men in women's clothing as ridiculous and laughed at them, that's why it when it was portrayed in media, it was for comedic effect to laugh at for it was viewed as so ridiculous, nothing to do with being pro-trans, anti-trans if anything. These days if a man dresses in women's clothing, it's viewed as "brave and stunning" and we're expect to take them seriously and if we laugh at them we are deem "hateful and bigoted".