Dear Rabbi Simon,
Last year, I did not shave during the “9 Days” [leading up to the Fast of 9 Av]. My boss commented that it “was not a good look for me”…the implication being that my appearance was not quite in line with the professional demeanour that is expected at my work. Although my job is not directly in jeopardy by not shaving, it does contribute to an overall impression that might not be ideal during a time when my company is looking to “cut back”. I have heard various applications of the custom to not shave during the 9 Days, one of which is that once you reach a point at which you are considered to be unkempt professionally (typically after 2 or 3 days) that one could shave. I understand that this is not universally accepted. Sephardic Jews have an alternative custom restricting shaving only during the week of Tisha b’Av…of course, this does not apply to me as an Ashkenazi.
Please let me know if I can/should shave in the 9 Days.
Shaving during Three Weeks [Fast of 17 Tamuz until Fast of 9 Av], Nine Days, Week of 9 Av: Ashkenazic custom is to refrain from shaving and haircuts throughout the 3 Weeks. Nevertheless, in view of the circumstances you describe, IMO you may shave daily, until the week in which Tisha B’Av occurs [see below]. The reason for this is that the Talmudic prohibition of shaving/haircutting is only during the week of Tisha B’Av–as codified in Shulkhan Arukh (OH 551:3). The Rama records the Ashkenazic minhag (551:4 end) of applying this expression of avelut (mourning) from the Fast of 17 Tammuz, however IMO in your case you can be lenient with regard to the minhag, and uphold only the basic halakhic requirement. However this year (2019=5779), since 9 Av falls on Shabbat and the Fast is observed the following day (starting from sunset the evening before), there is no “week in which 9 Av falls”. So in practice, this year you need to refrain from shaving only on Sunday of Tisha B’Av itself.
(I say this deliberately, as my view is that you should also shave lichvod Shabbat on Friday 9 August, even though that Friday is 8 Av. It is misplaced piety to shave day by day for work, but not to shave on Friday for the honour of Shabbat.)
Rabbi Rashi Simon