This is just my observation, but I think when the Holiness standards were set down the country was already in a more moderate state of mind and, therefore, the scriptures in
Deut 22:5 and
I Timothy 2:9 were taken at face value and not studied out.
When things began to change and the assessment was the "flappers, WWII and Rosie the Riveter" reared their head and were changing the countries values, men wanted to curb this by defining themselves on dress.
Back when this was laid out, it was accepted because the core of the church was still living a more moderate lifestyle in dress. Even us as Catholics wore dresses all the time.
Even for myself, I never thought there was more to
Deut 22:5 than simply a gender distinction of clothing. I didn't look at that scripture closely until just the last four years. I didn't study out
I Cor 11 until that time either.
What I focused on more was trying to learn to not lose my temper (lol), how and why does God keep loving us, keeping a consistent prayer life, and the basic tenets of Christian service and faith. The other scriptures I referenced, never occurred to me at that time.