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Most women in my surroundings dress quite immodestly, unfortunately. But, sometimes, a woman does dress modestly. Is it a good idea to tell her something like "I like your long dress" or "It suits you to wear long sleeves"? The two conflicting considerations are:

  1. It is immodest to speak with other women on personal issues, especially those related to their looks.

  2. Women care about what men think of their dressing style. So, such a compliment may give her an incentive to dress more modestly in the future.

What do you suggest?

EDIT: after reading the comments and Ana's answer, it seems that the question can have different answers in different situations. Here is the specific situation that I referred to:

  • The women in question are in the workplace. Most of them are not religious and probably don't know much and don't care much about halachic modesty. But, they probably do care about what men think of them.
  • I am married and not interested in any of the women. My main interest is to somehow encourage non-religious women to dress more modestly.
  • The question is also relevant to religious women, that are encouraged to dress less modestly, e.g, because the get compliments from non-religious men around them. Perhaps a man complimenting their modest look might have a corrective effect.
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    Avoda Zara 18a is perhaps relevant in that flattering someone over their modesty could encourage an increase in outward displays of modesty in order to be noticed even more - which is contrary to the point. (This could also apply to flattering someone over any religious observance, but the irony is more stark with modesty). Of course, that's just one consideration that might apply in some cases. I can imagine various situations where encouraging modesty with compliments might be a good idea. – Fred Aug 20 '15 at 8:05
  • Hi, Erel. Could you just clarify the parameters of your question a bit more explicitly, per my comments on the below answer? – Fred Aug 20 '15 at 8:21
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    Are you sure that in a non-religious environment complimenting someone on their modesty will be taken as a compliment? I think telling someone who isn't observant, "I really like how you've covered up" is both awkward and probably inappropriate. – Daniel Aug 20 '15 at 12:31
  • @Daniel: I meant a comment such as "this long dress suits you". – Erel Segal-Halevi Aug 20 '15 at 12:49
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    @ErelSegal-Halevi Ah I see. That's not what it seemed like to me from the question. You asked if it's a good idea to say something like "I like your modest dress." Perhaps edit to clarify? – Daniel Aug 20 '15 at 12:51
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I work in an all-women's religious workplace, but we certainly have visitors who come from different backgrounds than we do. Sometimes, we visit them, too.

From where I sit, complimenting a woman on the way she behaves in any way other than strictly professional ("That was a really helpful comment, thank you."/"The project is right on time, keep it up.") is pushing the boundaries of modesty. Commenting (favorably or otherwise) on her mode of dress is way, way over the line for a man.

Obviously, this is not a halachic ruling (although I suspect that halacha could be found to back it up, halacha to back up a more lenient approach might well be found as well). If personal sensitivity is being solicited, here you have it.

  • Thanks. I would never have thought otherwise in a religious environment. The issue is that, in non-religious environments, women often receive compliments from non-religious men praising their non-modest appearance. So I thought a converse compliment could be helpful to balance the situation. – Erel Segal-Halevi Aug 20 '15 at 12:20
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    @Erel, I understand what you want to achieve and it is a good thing to do, just try to depersonalize the comment in some way, so that it does not seem immodest. For example, make statement while other people are present and don't direct it to just one woman but to all women who dress normally, give some kind of depersonalised compliment to all of them at once thus excluding the possibility of misinterpretation.. – Ana Aug 20 '15 at 14:07
  • @Ana you mean something depersonalized like "I like it when women wear long dresses"? – Erel Segal-Halevi Aug 20 '15 at 14:11
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    yes,and you list all of those who dress like modestly "e.g. Rebecca..." (even if that is a short list), you can add that they have style because if we are talking about workplace environment it is not just tznius issue, it a style issue as well. – Ana Aug 20 '15 at 15:42
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    @Ana I'm not sure that the phrasing of your idea and naming anyone, even in a list is safe or useful. I would just say, generically, "We have an office (suggested) dress code and I'm glad to see that most of you are following it...", or something similar, without addressing anyone by name. It leaves things neutral. Then again, sometimes, silence is the best solution, esp. when it's not your business, anyway. If something is problematic, the manager should handle it. – DanF Aug 20 '15 at 19:17
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I will give you my opinion as young woman. I think you should not comment her dressing at all whether she dresses modestly or not. You should try to not even look at woman in that way. If a woman in not modestly dressed, other women from community should instruct her how to dress. If she is modestly dressed than she will not receive such comments and she will know she is dressed appropriately. It 's not your mission to give her compliment like that. If all the other woman are immodestly dressed then maybe the community is too liberal for you and you should think of finding more suitable community. But I have a feeling that something else is going on here :) if for example you seriously like the girl, that's ok, but make your intentions clear and straight, don't comment her dressing - just start a conversation about the real topic.

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    What if, for example, this is a case of a guy complimenting his sister? Or a girl complimenting her sister? This wasn't specified in the question so far as I noticed (assuming Erel wasn't specifically limiting the question to his own personal situation). – Fred Aug 20 '15 at 8:17
  • Actually, rereading the question, OP seems like he may have been specifically referring to a stranger after all. I'll ask him to clarify. – Fred Aug 20 '15 at 8:20
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    @Fred I think father's or brother's comments are not the topic because that kind of comment would obviously have educational function and could not be interpreted in any other way.. – Ana Aug 20 '15 at 8:37
  • after hearing the details, my answer can only apply on "in synagogue" situation – Ana Aug 20 '15 at 9:02
  • You gave a great answer. I also believe, that commenting on a woman's dress in the workplace may actually become grounds for sexual harassment, even if you didn't intend it this way. In most cases, the definition of harassment is up to the interpretation of the recipient, not the complimentor. Even if he were exonerated of the harassment claim, it's not worth the possible negative publicity to even try any type of compliment for any reason. – DanF Aug 20 '15 at 19:10

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