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

I also didn't realize that this was 4 years ago.

I am just going to point out that taking a picture of someone without their knowledge or consent, on base, in the chow hall, and then posting it on a social media site will get you in more trouble than her wearing the wrong shade of lipstick. I agree that she should be corrected, but you should be also. You could ask your question without posting the picture. I'm not sure what base you are at but most have policies that restrict photography, especially of an unwilling participant. Just my 2 cents.

There was a CG of III Corps at FT Hood who was famous for go after soldiers who did not salute his car (official sedan with Three Star Plate). If he spotted a miscreant, he stop the car and launch his Aide to conduct on the spot corrections. It is reported that one day a soldier from the 1st Cav Div failed to render honors. The Aide was launched, the young soldier was at the bus stop for the post shuttle. He evaluated the situation and immediately took advantage of the bus passing by. The large "saddle blanket" on his left shoulder was the clue as to who he was.

Late when the III Corps CG and 1'st CAV CG met the III Corps Commander brought it up and ask the 1st Cav Div CG about. 1st Cav CG said, "damned resourceful soldier if you ask me."

If you know for sure the Airman / female was blatantly out of uniform, you had every right to confront this Airman. But I think the thing that really should have been done was to contact the first higher ranking person or another Airman of this females rank and inform them of the situation. Then have them confront the female in question. If they blow you off and don't correct the Female about her abuse of the Regulations. this Higher ranking Airman would be just as guilty as the female for not doing a corrective action on the spot. But if nobody else was around and you had no choice but to confront the female. Do so in a respectful manner and tell the Female that according to the Regulations. She's out of uniform by wearing the non authorized lipstick. If she jumps your arse for trying to correct her, even if you are junior in rank to her. Get her name and ask her what Unit she is in, if she doesn't give you the information. Then try and find a Higher ranking Airman and report her for the violation. If she gives you her info, then report the info back to your chain of command and let them deal with this female. If they refuse to do anything about it, then I'd call the IG Department and make a formal complaint on the situation. tell them everything that you did and who you reported the violation to. Wouldn't hurt to write down everyone's info you contacted about the situation. Record keeping will / would save your arse in the end if she denies that you tried to correct her or have a higher ranking person correct her.

As an E4, I once corrected an E7. That's when this E6 told me I am never allowed to correct a superior. He asserted that I am only allowed to correct those of equal or lesser rank. (Later that day, the E7 apologized to me and admitted she was in the wrong. But that E6 continued to hold a grudge against me.)

I would definitely proceed with caution and discuss this with others as well as your next line supervisor and then let your supervisor handle the situation . If it is something that is obviously an egregious conduct, like assault or rape, then I would personally and immediately intervene and call for help, If not, then I would relay my sentiments to my senior NCO or if it is that person, the next commission officer in your chain. Believe or not, the Chaplain is always a good stop to discuss any situation that troubles you. In any case, the Sr NCO will not feel obligated to listen to your criticism of him or her.

Well, it sounds like it's airforce so she's probly fine the way she is.

Absolutely, when you mention it, ask the senior ranking NCO if you might have a word with her in private. Your superior is not supposed to call you down in front of your pears, and the same should go for your "helping" your superior. I am assuming that you are female and this is fine for you to do this, if you are male, find a female NCO that can council the SSGT. I had an Afican American A1C that was wearing a nose ring with her uniform in the office. I checked the regs (at the time, AFR 30-30) and the reg called for the ear ring to be discreet, but didn't state that the ear ring must also be worn in the ear (thus the name). I went to a black female MSGT and asked what she though? Her answer was, "Say what! Let me take care of it." The problem was solved in about 3 minutes and no one was overtly chastised. Sometimes the soft sell works even better than the raised voice. Sometimes these things happen out of ignorance vs. blatent antagonism. Think about how a creditor works, and they do not send the first overdue notice as the "hard sell".

Loyalty is telling the boss what he needs to hear, not what he wants to hear.
Juniors but be warry and respectful of doing this. As a E-6, I pointed out to my 0-3 boss that the 0-5 had his rank on backwards. The goal was to advise him without embarrassment.
Leaders need to be open to, at the right place and time, disagreements from their juniors. I would establish a free exchange zone (my office at morning meeting) where they could tell be what they felt they needed to tell me. I had the best Department in LARGE part due to great comms between my people and their chain-of-command, ending with me.

If possible, I would look for the same rank female in my platoon, ask her the same question you were asked on regulation and without pointing show her the SSGT
And ask if she is in regulation.
Then hopefully someone wil confront her.
At least that's what I would do.