I don't know whether this post should be in "Crossdressing" or "Clothing, Beauty," forum as it is more about a CD style issue than specific dressing items.
When I first began to serious crossdress fully as a woman, I concentrated on becoming the prettiest and most beautifully dressed woman I could be. Well, I've come on the stark realization that 1). At 6'1 and 230 with size 14 feet and masculine features, I could not pass as a pretty woman at midnight in a coal mine, and 2) the more I attempted to add makeup, fancy clothes and bigger boobs, the more I looked so much different from most women my age.
So, now I simply dress and make myself up to "blend in" with the women I see shopping at major retail stores like Target, Walmart, TJ Max, etc. If I can simply look like, dress like and carry myself like the average woman I see there while shopping, I will have achieved my goal.
For example, I just got back from shopping at TJ Max and Target. I wore a peasant top (over bra w/sm forms), jean skirt, and flats, my grey wig, fem watch, and everyday purse. I wore just a little makeup (used foundation, powder, blush, eyeliner & a little mascara, but no eyeshadow and light lipstick). It was an 'everyday casual' look of a 60-70 year old, matronly shopper who is somewhat overweight! I felt like I really blended in with those shopping around me. Of course, I had to be careful about my deportment and mannerisms and, when I spoke, I did so at barely above a whisper. Feeling this confident, I was not so afraid of being noticed or otherwise 'busted' and I had a truly enjoyable experience.
Since my primary occasion to go out dressed en femme is to go shopping or to a restaurant, this "Blending" objective works pretty well for me. If & when the time comes for me to attend a social gathering, etc dressed, I'll then need to step it up a bit, but at least I'll have a solid basis to work from. For now, though, my focus will be on "blending in" rather than "standing out"!