Hi Kiteless;
I agree totally with what Eva Marie says. These days I spend about 95% of my time dressed as myself, just 5% as my alter-ego. Being a woman of later years I think I have found a reasonable medium. I was just in the United Kingdom staying in my UK cottage for the last month and had time to catch up with some old friends and new friends (mostly women). One cis female friend that I met up with a couple of times took me to a couple of social events of hers (a handbell group rehearsal - 6 women and 2 guys and a pub quiz night). I was obviously a bit concerned not to over dress although the quiz night was in a pub full of people. Her comment to me was...Judith, you are very convincing as a female and blend in very well.. Obviously it helps that I have been on HRT for 3 years, have 44B+ bust and now womanly curves, no Adam Apple (never had one) and small hands and feet. But importantly I try to dress my age.
I also went to my local beauty therapist in Devon and she commented that I looked really great - she only sees me when I am in the UK, I went to her for a full facial and to get my Express lashes done (False lashes that last 10 weeks) and my eyebrows shaped and tinted. Again she tells me every time that that I am very convincing now and most would not realise that I am pre-op. I can tell you that getting lashes and eyebrows done helps considerably too.
I also 3 years ago had my Colour Analysis done (UK House of Colour) and have worked hard on my colour co-ordination including lipsticks, blushers and nails. Although I love high heels, these days I rarely wear them and if so tend to use wedges. But I rarely wear jeans or trousers, although I do have some really nice black leather pants and some flowing trousers and skinny jeans. But I spend almost all the time in dresses and skirts as I find them actually very liberating after all those years having to wear trousers!. In fact my deportment coach said in summer its best to just wear a soft off the shoulder skimpy "A line dress" that will move in the breeze. Don't over dress!. If you must take a long line cardigan or short tailored jacket. Most of my dresses and skirts are just above the knee. I.e. Nothing too short. Though I do have some really nice denim shorts. These are quite short! and I have a nice denim skirt too (although that's just above the knee).
For makeup, during the day I only wear a light coverage of Bare Minerals Liquid foundation, blusher, lipstick (soft pink or nude) and mascara (I get my eyelashes tinted), but at night time put on eyeliner and eye shadow and highlighter, plus a stronger colour lipstick e.g. Ruby red. I don't go in for younger colours. I always have my nail and toenails nicely manicured and painted with colours from my House of Colour guide and matching clothes swatch. For Nail varnish I always use OPI - Big Red Apple is my favourite, but I also love other two colours - Is Mai Tai Crooked and Cosmo Not tonight honey. Mascara is Dior Show - Blue Black Intense. I do like wearing open toe sandals (and of course open toe pantie hose). Note no bare legs for my age! If anything I focus on dressing down to blend in.
Mind you it was lovely weather in Devon and I even braved it and went out and sat on one of the beaches in my new one piece swimsuit. That's a first for me, although I didn't venture into the sea this time
One key thing is don't try to be over feminine. Just be natural. Keep you head up when walking and don't forget to smile to people passing you by. You will be surprised at how many people smile back and then don't give you a second glance! Best of luck.
Hope this all helps
Judith Lynn