When I look at modesty (haha, pun!), I find that there are more varied aspects than seem to be accounted for in the popular use of the word.
Modesty: The principle appears to me to be about humility, an expression of true value, seeing oneself as God sees, and the way that principle should express itself.
If you search scripture, there is no dress code. Unless you’re a priest and on duty. For everyone else, there are rules about what can or can’t be worn (with fringes, sans mixed materials. Plus/minus debate). But what we normally think of as modesty in the church (hem length/cut/etc) are not found in Torah. In fact the mark of a prostitute in some places was what they covered, not what they uncovered.
If you look up the word modest in the KJV, you find it in reference to the instructions not to wear expensive clothing, not a definition of yardage. Which makes sense of the word modest, which means neither too much nor too little, but fitting (another pun!). Torah doesn’t forbid wearing beautiful clothing, in fact some seem to imply it is good when on a godly person, so it seems the apostles aren’t talking about a blanket prohibition (they keep on coming!), but that godliness should not be in show but in substance.
But the things they use to express this warning is not with the danger of revealing wardrobe, but the danger of showing wealth. Unless you have a certain amount of status you can’t afford the time/money/ or energy to be fashionable. I think there’s space for fashion as art, just as its not wrong to make a dish taste good rather than simply nutritious. Or just as its not wrong to sing well rather than just sing. Or do anything well. But the point is, especially back before the industrial revolution, clothing was a sign of status. As was plaited hair, and definitely jewelry. To dress well then, in a way was to publish how rich you were. A kind of competition that sowed division.
In Jewish religious circles, it is commonly understood that modesty is really about humility. Not drawing undo or undeserved attention to oneself. And that is something you can find in the Torah, because even the King was not to think himself above his brothers. If you love someone else as much as yourself, it leaves no room to make yourself more auspicious if it means making someone else more lowly. Your desire is for them to live with you, not beneath you.
So then, dress is just an expression of modesty. In truth it should include every action, word, or thought. Even totally naked married men and women should be and can be modest with each other, because they are humble. And what is this humble thing? It is not thinking one less than one is, because that would be to deny the image of God in you and the work of God in transforming you into it. To degrade the creation is to degrade the Creator. Nor is it to think oneself higher than one is, for that is obviously pride, and also discontentment as you claim a position higher than the one God gave you, thereby saying to the Potter, “What are you making?”
Humility is simply seeing yourself as God sees you. Who or what is the focal point of humility? It is God’s perspective. So what is lack of humility? It is focus on the perspective of someone other than God! So then if you dress in a way that promotes the beauty of the body as a praise of God’s handiwork and greatness, then that promotion by dress is humility. Just as singing God’s praise by a gifted singer is not exhibitionism, if they are showing off God rather than themselves. Likewise, covering because of shame of the body or revealing for the praise of anyone without God would also be immodest.
Thus exhibitionism of self is always immodest, and selflessness is always modest.
Expression of Modesty in Dress: But are there practical considerations? What about the complication and deception of lust.
From the first understanding, I think the idea of modesty must revolve around an objective. It’s not omnidirectional, it does not have one definition, but takes many forms. Modesty must revolve around a specific objective. Therefore neither more, nor less, is inherently modest but the reason for it. For example, if one is swimming then extra yardage makes swimming more laborious even dangerous. Therefore wearing less is modest. Perhaps even wearing nothing, just look at Peter. No one seemed to take issue with the fact that he is working without attire. Do we suppose this is the first time it happened? Or that it never happened afterwards? This was just the one time Peter decided to go au natural without any consideration for what anyone including his Rabbi might say?
Having said that. If my objective is to minister to others, where they are, then shouldn’t my dress reflect that objective? Perhaps Peter was ok because everyone understood that his manner reflected nothing other than practicality.
That sounds reasonable, so does that affirm the idea of asking women to be concerned with how their attire might distract or cause a man to stumble? Perhaps, yes and perhaps no. Perhaps, more nuanced than that. On the one hand, if a woman (or a man) knows that what he’s wearing would cause someone else to stumble, then it seems she or he should abstain. But notice it is not because it is inherently wrong, rather it is an act of sacrifice for another. If they did not know they were stumbling someone, then it could not be their fault because no one can be expected to abstain from everything that might offend. Even Godly things can offend. The very fact that someone can do something not inherently wrong and it might offend, means that the freedom of God is actually offensive to some. If a believer attempted to abstain from everything that could offend, they would have to abstain from life itself.
Further complicating is that, while one might claim to be offended by the freedom God gives us, isn’t the laying on of burdens by tradition also a stumbling block? If by abstaining, we take on ever-heavier load aren’t we falling into the criticism of Yeshua toward the Pharisees? While Paul seems to make a big deal of stumbling brothers, Yeshua goes out of his way to offend people on several occasions. This is the same man who tells his closest followers that they’re stupid/foolish at times. Tells one of them that he’s speaking for Satan. Clearly, there is a limitation to how much we can be inoffensive.
If Peter was concerned about expensive dress, what about having a nice car? I won’t lie, my car is ‘junk’ in the natural and it’s very easy for me to look at someone’s car and say, “If only I had. . . ” Does that mean everyone else is required to sell their nice cars? How low is the bar set? Do I have to give up my car for someone who is even lower on the food chain?
The only conclusion I can reach then is that people of either gender should be considerate in specific with a specific person who has given them reason to believe this is a hurdle for that specific person in a specific time. But that in general, such a standard should not be observed and the general community should call each other to true understanding and not entanglement with tradition-made-into-command, but rather one of true modesty which is defined by the need of the situation and not some artificial imposition. But since sometimes practicality leaves different options of style, and since we don’t want to encourage division just as we wouldn’t with jewelry, then one should dress in a way that is generally acceptable. Neither outstandingly ‘conservative’ because of the message that projects, nor outrageously ‘liberal’ because of the message that conveys.
I guess what that leaves me with is, nothing is either forbidden to wear (except for the Torah prohibitions) or required (except for the combinations Torah requires). But that we should take reasonable consideration for the message our attire projects and ask whether it is projecting what we mean to. Does it achieve our objective?