Getting caught is always a concern for me, as I go out (all the time now) in my hybrid dress mode. Gurl jeans, shoes, undergarments and shoes. Flats or booties.
I live in a “liberal” town, but everyone dresses pretty conservatively, with the men in “uniform” e.g., matching bermuda shorts, polo shirts et al. One time (my funny story and sorry if you’ve heard this before), I was outside a store downtown waiting for it to open. I was wearing capri length jeans, black flat, my legs are always shaved smooth, and a regular white shirt. Up walked up a couple I knew. They stopped to talk, and the male is a very self centered person. He was going on and on about him and how he worked hard to get his son into a prestigious college. His wife however, was looking me up and down! She was obviously in tune with what I was wearing! Her facial expressions were somewhat questioning, but the real funny thing was, I gave her the once over and she and I were practically wearing the same outfit!!!
Her top was a different color! They went on their way and all I could do was laugh about it. He did not notice a thing!