When it comes to clothing malfunctions, when is it right and wrong to inform someone?

Maxemeister
Context to my situation: Today, I was sitting at lunch and a friend of mine (female) laid her head down. Her thong stuck WAY out of her pants, what many would call a whale tail. Now, sure, I have a slight crush on her and in some ways it's a nice thing to see, but mostly I was worried about others seeing and her being embarrassed.

But, wouldn't telling a girl that her thong is stick way out of her pants be utterly mortifying?

I've heard mixed answers from girls on GAG. Sometimes they appreciate being told, but I think it might differ from situation to situation.

When is it okay to let a friend know about an outfit malfunction? When a button is lose? When your undies are full-on out of your pants? Where do you draw the line because it would be too embarrassing?
When it comes to clothing malfunctions, when is it right and wrong to inform someone?
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