While it may be rare in our modern Western world, there are some Christian communities and church leaders that hold to a more strict and more conservative view on women's fashion and modesty.
Some church leaders prescribe what types of clothing a woman should or should wear in her everyday life, and sometimes that may include the claim that women ought to never wear pants or jeans. Again, this is a rare assertion, but it does exists in some contemporary church circles.
In this episode, Kenny talks about how modesty shifts dramatically from culture to culture, therefore specific prescriptions as to what a women should or should not wear misses the more important Biblical value.
Ultra-conservative specific prescriptions on women's fashion or clothing miss the grander point of how we ought to approach modesty in our culture in a way that points people to the Gospel; and Kenny goes as far as to say that making any such specific clothing prescriptions certainly leads Christians into the burdensome category of legalism.
Kenny makes it clear that he is far more concerned with how you determine what you wear than the actually outfits themselves. He then gives listeners four reminders to consider as we approach the topic of modesty:
1- Be different than the society in which you live.
2- Be more modest or more conservative than others in your culture.
3- Be careful that your clothing doesn't cause the opposite gender to lust.
4- Make sure you spend more time on your heart and character than on your outward appearance.