Gender is a spectrum. Most people are going to fall somewhere in the first few standard deviations of gender expression. If you removed gender roles and prescriptions, people would feel more free to vary their gender expression. However, we would still see a bell curve distribution in which most people are going to fall in the middle somewhat. So for example, I might be theoretically inclined to explore wearing makeup, wear earrings, or even get a butt implant. Sex, on the other hand, being bimodal, plays some role in gender due to hormonal distributions but is not the basis of it.
So for classical progressive thought, we had more freedom like the recognition and reduced shame of tomboys and to a lesser extent more freedom of expression to boys. Sex was a constant and was not influenced by what gender expression someone decided for themselves. Woke progressives, on the other hand, believe that the expedient cure for gender dysphoria is to uphold the strict binary and have the sex change through hormone treatment and bodily modifications to match gender with sex. For example, I had seen on Tiktok that the late Kurt Cobain was being referenced as a trans-woman because he wore makeup and heels at certain times. If sex and gender are seen as close to independent of each other, the natural cure to dysphoria would be therapy to dissolve societal notions of gender to acquire self-acceptance. It's only when sex and gender are seen as essentially-linked that aspects of one's sex are changed to match their gender as a cure for gender dysphoria.
The disfunction lies at the underlying insecurity the latter view brings. What level of deviation is ok before I start questioning who I am? Why can't I just be a man who explores things differently from others? Why do I need to change aspects of my body to fit society's notions of the binary instead of accepting that I'm different? I can imagine that this must be destabilizing. I am myself feminine in many aspects such as high-aggreableness but have been fortunate to not have been introduced to the idea that because of that I shouldn't think of myself as a man or cast any doubt on that.
I hope that clears things up. I do think Wokeness is a sickness and destructive, but I was primarily using the "subversively destructive" qualifier because of the attack at the core of how we view ourselves and how we solve race relations.