On what was written in the answer to Men’s Pajama Pants for Women, does the same apply to men – namely that wearing women’s garments underneath clothing would be ok, for example wearing tights for warmth or comfort, under long trousers, or would that be assur/better not to do?
If the tights are worn specifically under one’s clothes, it would appear that there is no problem (though some are stringent).
If this is being done for warmth, there is still greater room for leniency.
Sources: See Beis Yosef 182:5, and Bach, who writes that the prohibition applies specifically to clothes that are a kishut, meaning worn for show.
Moreover, the Iggros Moshe (Yoreh De’ah 1:62) writes that the prohibition applies specifically to the result of looking like a woman, and not to the very act of wearing a garment, and therefore it would not apply to the case at hand.
A further reason for leniency is that the garment is being worn for warmth. The Bach and Taz (182:4), among others (Avnei Tzedek, Yoreh De’ah 72) write that it is permitted to wear women’s clothing for purposes of warmth or for protection from the sun — though others are stringent in the matter (see Shach 7; Yad Ha-Ketanah p. 279).
The above-mentioned Avnei Tzedek relates specifically to clothes worn under other garments, and is lenient, and see also Shut Shevet Ha-Levi 2:63 (Yoreh De’ah) — though the Minchas Yitzchak (2:108 sec. 3) is stringent on this issue.