The one time I got "outed", was when wearing a hat. I work outside, part time. It's get's windy as hell, so I ALWAYS wear a hat. That alone drew some suspicion. However, actually looking at myself with the hat/wig on, it's not too hard to see it's a wig. The hat actually cinches down the piece and lifts the back up a bit. Screws with the blending. Almost drove me to go full cap.

The good news, is that about 17 out of 20 people in the room had a shocked/confused look on their faces.