i think you have to pick your battles with any boss. you have to determine how much you want to challenge him on this (or any) issue. there’s a fine line between not getting walked all over by a boss and not wanting to start a war. depending on the circumstances you work under (i.e. contract, can you be fired easily) depends on how you treat this issue. i am a civil servant, union shop steward, hard to fire, but i don’t challenge my boss on everything. you can always “yes” him and then return to your present way of shaving in the future. if you have a good relationship with him you could approach him and ask him to clarify what’s expected of you appearance-wise. if you’re a hard to get rid of employee, like if you work under a contract, you could challenge him. my feeling on challenging him is to be careful how you do it because you could start him busting your chops on other things, like if you come in late occasionally, or if your work is not up to par in other areas. if he does not like your challenging him, for example by asking him “show me where it says i have to shave” he might all of a sudden start nit picking in other areas of your job performance. while it may be illegal for him to request you shave, there are ways he can “get you” if you win this battle. so evaluate your relationship with him and how cool he is, and determine whether this issue is worth the challenge or if it’s easier handled another way. you do have to continue working for him and so it’s a fine line…..or you could challenge him and see what happens and if he really becomes a ballbuster just look for another job. that will also come into play with your decision, how much you like your job and want to remain. you may win the battle but lose the war.