First, let’s make sure we’re on the same page for our terms:
Cross dresser: a person who wears clothing typically associated with the gender opposite of their own — in opposition to social/cultural norms. In most western cultures, a man who wears a skirt would typically be considered a cross dresser. A woman wearing a tuxedo might be considered a cross dresser, but in western cultures, it is generally less controversial for women to wear masculine clothing.
Gender Dysphoria: the distress or problems functioning caused by the conflict between a person’s experienced gender, and the gender they were assigned at birth and/or their body’s sex.
One more concept which is important is that transgender men are men, and transgender women are women. The gender a person feels is their gender, regardless of what was assigned at birth.
Ok, so can a person who cross dresses experience gender dysphoria? My answer is yes, but probably not the way you think.
Say we have a person who was assigned male at birth who experiences gender dysphoria. By definition, they are not a man, because that is the gender/sex assigned and Dysphoria requires there to be a conflict between the person’s assigned sex/gender and the one they experience. So if this person wears feminine clothing, they are wearing clothes which are in alignment with their gender, which disqualifies them wearing those clothes as an act of cross dressing.
But here’s where it gets interesting. Arguably, a person who was assigned male at birth whose gender is feminine would be cross dressing by wearing masculine clothes. Most people assigned male at birth are dressed in masculine clothing at least until they are capable of expressing their true gender. And that same person may very well feel gender dysphoria, as that is quite common when one’s experienced gender doesn’t align with the one assigned.
This was the case for me. I am a transgender woman, and I definitely experienced gender dysphoria. Once I knew I was trans, I experienced more intense dysphoria when wearing masculine clothing! And since I was a woman wearing masculine clothing, I was technically cross dressing in them!