Q. Someone is taking needed medicine that causes as a side effect dry skin and very painful dry lips. Can he use in Yom Tov a lipstick for treating his condition? Placing oil or Vaseline on his lips, does not seem to help much.
A. Shulchan Aruch (O.H. 327: 1) rules that one should not use oils when done for medicinal purposes. However, Poskim permit when there is great need. (Be’er Moshe 1: 36).
Poskim prohibit the use of lipstick on Shabbos and Yom Tov (Igrois Moshe Orach Chaim 1:114, Yabia Omer 6: 37, Menuchas Ahava 13: 6, et.al)
Horav Shlomo Miller’s Shlit’a opinion is that in since the stick is solid, one should not use it on the first day of Yom Tov. However, on the second day which is only Rabbinical, when in need he may use with a shinui, or change such as holding still the lipstick in one’s hand, and moving the head and lips around it.
Rabbi A. Bartfeld as revised by Horav Shlomo Miller Shlit’a