I looked at your introduction and a posting of your picture. Without knowing your height and weight your facial features look "soft" unlike mine which look obvious masculine. You also indicated you have a supportive wife. I have been out for evening drives which are relatively "tame" unless you dwell on the possibility of a car accident or being pulled over by a police officer. I am six foot tall and 200 pounds. As a male that height and weight is great. Not so much for flying under the radar. Many years ago I decided to take strolls in my neighborhood in the late evening. On my second trip out the door I was walking down the street which with hindsight was a mistake. I heard a young woman who lived several houses down the street talk loudly to someone else that she had called the police to report a man was walking around in a dress. That made me very uncomfortable. First because my wife would not have liked my cross dressing to become know in the neighborhood, and secondly, she just does not approve. Hence forth I now go to a residential area in my small city that has grocery stores and restaurants that are open into the late night (pre-covid). On several Halloweens I did make an effort to go into grocery stores and a donuts shop totally en femme; heels, hosiery, dress, makeup, wig, the entire deal. Of course Halloween is a cross dressers dream. I would recommend, if your wife is on board with your cross dressing, have her accompany you on a stroll. It gets dark relatively early now, so a stroll at 5 PM or 6 PM is not like a stroll at midnight. I think she'd be sort of like a security blanket and two women walking together really attracts less attention than a lone women out and about. I think there is less chance of an undesirable trying to pick you up. I found after awhile being out for a stroll becomes rather boring. All it did for me is to fulfill the desire to feel the cool air playing with the skirt of my dress and slip. I get the urge out of my system. If I had an accepting wife I'd much rather stay at home.