Is it appropriate to confront a higher rank when they are blatantly disregarding regs?

Yes you can bring it to their attention that the lipstick that she was wearing was not with in the regulation. But you might want to do it in private and not in front of everyone.

Absolutely it appropriate and required to address reg infractions! It’s wise to do so professionally!

But, to answer your question, yes, it is ok to let higher ranking members know that they are out of reg but, yes, be nice about it...

Not only is it appropriate but it's the law! Though I agree with CSM O'Black (below) I was always known for not being that "tackfull". Because of my former job in the Army I was consistently asked by Junior and Senior Officers (including flag officers) about the "appropriateness" of either doing somenthing or authorizing something to be done. If that "something" was contrary to Army Regs, Federal Policy or the UCMJ then I told them so without so much regard for rank...not that I meant disrespect, but, there you have it.

OMG in this man on man kissing pink wearing underwear military you actually have regs on lipstick almost funny

This is a difficult question and it is a relative one depending on the situation. There was an old saying when I was in "Regulations are open to interpretation; He who has the higher rank has the right interpretation." Because of some ambiguity in some regulations, policies, or local rules, it is best not to argue; unless the rules leave zero ambiguity, and ask the guidance of a Judge Advocate General Officer, or the author of a policy, for example, a commanding officer can write local policies for their unit.

Bottom line, it is okay to question, but if their response is that they are in the right, yet you are still not convinced, leave the conversation go ask someone who can make a proper interpretation of the rules. Otherwise disagreements could turn into tensions, which could be misconstrued as disrespect. Not everyone is level headed and as I sometimes saw when I was serving, rank can go to someones head pretty quickly.

No you shoud find out her name and where she works and advise her NCOIC that the issue needs to be adressed.

Well if the 2 Star decided to ignore, what does that tell you about our political correctness?

Yes, and I am with CSM O'Black who said use tact and respect when doing so. I was a junior Captain on Nuclear Alert with my aircrew, and we had a Brigidear General pulling alert with us as an alternate to the "Looking Glass", a 24/7 flying command post. He was like the #2 designated survivor for running WWIII if it happened. This BG decided he wanted to have a "discussion" with the 5 aircrews on alert, and his thing was wanting us to have pressed flight suits and spit polished flight boots. After hearing him out, I then asked if there had been an addendum to AFR 127-2 para 4 countermanding that no flamable material may be added to our uniforms when flying, nor could we dry clean our flight suits as it would remove the Nomex Dupont airamed flame resistance additive that was in our flight suits. Case was closed, we were never asked to dry clean or polish our flight suits and boots again.

As long as you use tact and show respect there should be little reason not to confront your superior.