To tell or not to tell

Here's a dilemma. You spot a co-worker, even your boss with an outfit faux pas that has definitely been going on all day. Their shirt is on inside out. Their back slit is still stitched up. They have a mysterious stain in a spot that would not be apparent in a mirror once over. Do you tell them? Or do you just chalk it up to an off day and smile and let it slide?

I am typically one to let people know when something funky is going on. If you mascara is smudging down your cheeks, I'll point it out (nicely of course!). If you have some food caught in your teeth I'll point it out as soon as I notice. If your skirt is tucked into your pantyhose, I'll run over and let you know immediately. I respond this way because if I am running around with some embarassing catastrophe all over my face, I would hope that someone would let me know, whether it is a friend, co-worker, or stranger on the street. Anything to avoid continuing humilation throughout the day, or whenever you stop and take notice that something is wrong.

Then there's the cases where someone is dragging toilet paper on the back of their stiletto, and clearly in view of their date at the bar. It's best not to cause a scene by going over or yelling to the lady that hey, you stepped in tissue and had no idea, now the hottie you are trying to impress will witness it. In that case, I would try to stick out a leg and snag the paper off with neither party any the wiser. Sometimes it's better not to call attention to the awkward situation.

That brings me to the case of the co-worker who you run in to in the bathroom at the end of the day. And, unless they've been doing a quick change in the stall before you bumped in to them, chances are they have been dressed in that very outfit all day long. You pointing out their mishap will embarass them (for sure), and not only that, call attention to the vast oversight it must have taken not to notice this all day. Her mind will start to race...How many people saw me like this? Did they notice and not say anything? How could I have let this happen?

Depending on your rank and relationship to said co-worker, and her mood at the time, her reaction could have a serious impact on your work relationship. She could laugh and remark about how crazy her schedule has been that she can't even dress herself any more. She could be mad, and take your helpful suggestion as an affront to her outfit. OR she could be so embarassed that she forever remembers you as the one who made her feel stupid just before leaving for the day.

Is it worth the risk? Or is it better to just leave well enough alone and claim obliviousness?