Considering all the posts you have commented on what is the opinion of your wife? Is she on board with it? Aside from that issue I have found my comfort zone for going en femme outside my home is drives and strolls in the early evening. It's starting to get dark earlier. If you want to check on the best dates for sneaking outside without your neighbors seeing you go on-line and check when there is a "new moon" and sunset, etc. You have not stated whether you live in a home/house or an apartment complex. The biggest issue many people have is security lights blazing away.

When I go out I turn off my outside lights. No chance of me activating my lights. My car is parked fifty feet from the street. If there is a "new moon" that eliminates moon light. No security light. Years ago the dome light in my car burned out and I have been too lazy to replace it. Hence, when I open the car door light does not flood the interior. You can always hank the dome light out for the evening.

If your wife drives a car I suggest using her vehicle for your drive. I would recommend getting a wig which would more closely reflect your wife's hair color and style. If your wife is a blond and your wig is red a neighbor may be curious as to who is driving your wife's car. The same inquiry may be made with a blazing redhead driving a truck.

Once you're on the road the question will arrive as to your comfort zone. I am six foot and 200 pounds. My comfort zone is not a mall. I choose a residential neighborhood that has stores and restaurants which the locals patronize. There are 24 hour grocery stores. In the fall and winter when it gets dark early it is not unusual to see women toting a grocery bag from the local Safeway on the way home. The eye sees normalcy. I live in Washington State where it rains too much in the fall and winter. Out comes the umbrella for a stroll "home from the grocery store." The umbrella is useful for me because it obscures my face and to some extent my height.

If you're going to go for an evening stroll I recommend comfortable footwear. High heels tend to make a lot of noise. I wear a wedge with a lower rise than my heels. The shoe also has deadening soles. No clicking to turn heads. It is not unusual to see young women walking home from a bus stop wearing athletic shoes. That can be a good choice to wear a women's athletic shoe with colorful laces and carry a clear tote with a pair of heels. In my small city there are steep inclines in the financial area so it is not usual to see women walking to and from work carrying their office heels in a tote to change into when arriving at work.

Once out of the home there is always the possibility of something happening for which you're unprepared. Carry a "man bag" with a change of clothing in case you get a flat tire. Make sure all your vehicle lights are working. I am way past the psychological need to wear nail color and excessive makeup on my strolls. I wear just enough facial makeup to make myself feel feminine but little enough to remove easily if necessary.

At some point you may find yourself ready for that foray to the mall and interacting with sales associates. If I was five foot six and 120 pounds I would be in that comfort zone. But, that is not to be in this lifetime. Maybe the next time around.