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Here, Rabbi Y.H. Henkin quotes his grandfather (Rabbi Yosef Henkin) as saying there is no prohibition against women wearing loose pants, and in fact they are exemplary ("yesh bo mishum tzenius"): "See Bnei Banim vol. 2 p. 211 par. 38, and vol. 4 p. 141 (concerning pisuk raglayim)." Here are the sources: ...

Taking it for granted that the issue of "male attire" is ultimately not the source for the prohibitions, a stance I believe is justifiable even if not un-debatable, there remains a significant opposition to women wearing slacks on the grounds of modesty. Although most noted for taking the hard-line position that wearing slacks violates the prohibition of ...

From the Sefer Nishmas Avraham Siman 182 וכן שמעתי מהגרש״ז אויערבאך זצ״ל לגבי בחור שצמחו לו שערות בין שתי גבות עיניו שזה נקרא מום ומותר לו להסירם: Uni brow is called a blemish and it can be removed. The Shulchan Aruch 182:1 itself holds like the Rambam that one can remove other hair from the body with scissors except for the armpits and bais ha'erva. ...

"Dog tags" are worn primarily, and until recently almost exclusively, by men. It would be very difficult to justify labeling them a womens garment. A more likely problem is that when one wears them outside of their intended purpose, i.e. as a style rather than to to identify a soldier, it may be similar to wearing a sword which may present a problem of ...

Most forms of "beged isha" (the prohibition on men wearing women's clothing) all depend on a given society's norms of what's called "men's clothing" vs "women's clothing." (E.g. a kilt is okay in places where men wear them!) While certain actions or categories may be objectively off-limits as "beged isha", I've never heard anything about a necklace-like ...

http://www.chabad.org/holidays/purim/article_cdo/aid/483409/jewish/Is-a-woman-allowed-to-dress-up-as-a-man-on-Purim.htm This prohibition is intended to prevent licentious behavior. The question remains, however, whether this prohibition applies to Purim, a day when any cross-dressing would only be for "harmless" entertainment purposes. The Rama, ...

See here. Summary: Mahari Mintz writes that although it is usually forbidden to dress as the opposite gender, it is permitted in the context of the Purim celebration. (It seems, though, that he is trying to rationalize a behavior he has seen as being accepted.) However, several earlier rishonim write that it is forbidden to cross-dress under any ...

Yes. It is normal in our current Western society for men to do such things (certainly for a unibrow), and the rule of thumb for Lo Yilbash is if it's normal, it's not forbidden (Shulchan Aruch and Rema YD 182:1). R. Akiva Eiger (ad loc.) cites a Perisha who writes that we look at the non-Jewish society around us to determine what is normal.

While I appreciate the desire for sources, you must understand that the issur of lo yilbash is much more subjective than many or most other halachos. Most likely you're familiar with opinions which prohibit from looking in mirrors, but that isn't necessarily the practice today when it is common for males to pay attention to their appearance in the mirror. I ...

The Lubavitcher Rebbe writes that he didn't hear any explicit instructions with regards to trimming a mustache (in the footnote it mentions that the discussion is only when the mustache impedes ones eating, though I don't know the source of this footnote). Moreover, there are logical reasons to forbid as well as to permit. Therefore, he suggests asking ...

As far as I know, the reason for women not wearing pants doesn't have to do with their being male garments. Especially today, nobody thinks twice upon seeing a woman wearing pants. I believe that the main reason for wearing skirts over pants is due to tzniut (modesty); however, a large number of modern poskim rule that there is no problem at all with women ...

In light of all the edits to the question... In order to forbid trimming the hair of the mustache you would have to assume that it is forbidden due to the prohibition of lo tilbash (loosely: men can't perform "women's" actions and vice versa) and that lo tilbash still applies to shaving despite the fact that the majority of men in the world shave their ...

One of the many reasons to not shave or trim a beard, is because Chesed of Hashem grows through the hair on the face, and by cutting your beard you may affect your 'reception' of Hashem's Chesed. The question then is if the mustache counts as part of the beard. Arguments exist for and against the mustache being part of the beard. Those kabbalists who say ...