The way I see it, if a person's identity is with Christ first and foremost, then there should be no issues with a woman dressing as a woman and carrying out the role of a woman. Likewise, the men should have no issues with being a man and taking the role of a man as it was in the first place.
The carrying out of these roles changes with each era, but the males always were the head of the family, and the women always managed the household. Women always dressed in a way that showed they were female, and men always dressed in a way that showed they were male.
Women are exhorted to dress in a way that emphasizes their character, not their looks. Women have a responsibility to dress in a way that doesn't put men in a weak position; men have a responsibility in this too by choosing not to focus on those aspects of a woman. A good character should be elevated above physical appearance in culture.
When men and women are secure in their identity in Christ, then they will not place so much emphasis on appearance but focus on being made in the likeness of Christ. They will also not have an issue with their roles as men and women, and be happy to be male and female and not confuse the issue.
When the issue of clothes becomes legalistic and misses the point behind such dress codes, then it is a problem. When issues of clothes becomes too lax then it also become a problem because like it or not, our clothes can have an effect on others that is not desirable or helpful or loving if we dress immodestly. If we are secure in Christ then it is not a problem for us to dress more modestly, and we haev our priorities right in loving others in the way we dress and honour our bodies and our God.
Not sure that answer was entirely relevant, but hey, I hope it's worth reading