I had a similar shirt and was wearing it BOTH times when I was asked. I carry a lot of my weight in the torso and thought that style of shirt was a fix for my problem. One of those times I was target shooting at an outdoor gun range with a male friend and this redneck woman collecting people's brass asked me if I was pregnant. I said No. Then she said: Well, did you USED to be pregnant? I'd been was reloading when she'd walked up and I looked at my friend and joked "Accidents happen". The woman finally got the point and scurried back up to the long gun range, lol.

I was wearing a shirt with what is probably similar ruching. The customer at my register was purchasing baby clothes for her soon to be granddaughter, looked at me and said "You must be due pretty soon too!"

The look on her face when I said "Nope. I'm not pregnant, just fat" was hilarious.

I still went and gave that shirt to my roommate.