I decided to make my resolution for the month "Become More Chaste in Thought and Deed" specifically because I believe the godly characteristic of chastity is the one highlighted in this passage. Rather than being hyper-sensitive to any and all possibilities for sexual stimulation and avoiding all such exposure, I believe the godly way to avoid the type of temptation embodied in "looking upon a woman to lust after her" is found in an expansive definition of "chastity" - one that goes beyond the more limited definition of avoiding sexual activity.
One definition for "chaste" that fits this construct is:
Pure in thought and act; innocent; free from lewdness and obscenity, or indecency in act or speech; modest (as, a chaste mind; chaste eyes).
The interesting association in this definition is the use of the word "modest" - which in context is defined as: "limited or moderate in amount, extent, etc." In other words, taking both of these definitions in the context of the admonition in Matthew, the underlying characteristic that Jesus appears to be addressing is "moderation" - being able to see and appreciate physical beauty without going to any extreme, without including "lewdness, obscenity, indecency, lust, etc." This is a much more comprehensive and fundamentally empowering / liberating view of "chastity" than a simple abstinence from proscribed activities. Also, and this is critical, the definition highlights being "chaste" as something primarily within the individual.
I am reminded of a story I heard once. I don't know if it is historically accurate, but it illustrates this characteristic in a very simple and direct way. According to this story, a woman notorious for traveling in the nude (Lady Godiva, perhaps) was passing a group of religious leaders (the Pope and some Cardinals, perhaps). One of the Cardinals told everyone to cover their eyes and look away, but the Pope did not do so. The woman saw the reaction her passing had created, including the fact that the Pope did not look away - and she asked him why he did not do so. His response was something like:
You are a daughter of God, and he has blessed you with great beauty. I appreciate that gift God has given and praise him for his gracious gift.
I believe it is important to remember that Adam and Eve covered their nakedness only after Satan pointed out that they were naked and that others would see it. I mention this simply to stress that the typical restrictions we employ as a part of this mortal existence are in place NOT because physicality and sexuality are bad things, but because we do not want to place undue temptation and stimulation in the path of others. However, if all were "chaste" in their thoughts and deeds, such restrictions would not be necessary. In other words, we seek "modesty" (moderation) in dress as an attempt to strike a proper balance between the ideal and the practical - between where we wish we were and where we are.
True "chastity," therefore, includes not only conforming to the societal constraints intended to avoid placing temptation in the path of others but also having our hearts changed to not be tempted no matter our surroundings - to not "lust after her" even when "looking upon a woman" cannot be avoided. I don't have a simple solution or suggestion for each person. I know it is neither the extreme conservatism of the Taliban in Afghanistan nor the extreme liberalism of South Beach, Florida - but I know that I must be able to walk in either world and be free of "lust" in order to fulfill the standard Jesus holds up in these verses.
In summary, my being chaste in thought and deed is MY responsibility. I can't blame the environment around me - or those whose appearance "naturally" might tempt me - or claim the devil made me do it. I must change myself ultimately, even as I change my exposure and environment and actions until I reach the point where they no longer matter. I can't dive into tempting situations in order to test my control, but rather I can change my thoughts and actions until I can face such situations without temptation. If I never reach that ultimate objective, I must continue to structure my environment to reduce temptation, but eliminating all possible temptation can never be the default. In the passage being discussed, the woman is NOT at fault for her beauty; the man is at fault for how he reacts to it. At its most fundamental level, "chastity" is NOT imposed externally; it is developed internally.
The Taliban is not correct in its interpretation of chastity; Jesus is.