Having spent so many years as male, I find it personally very liberating and personally preferable to wear a dress or skirt and blouse. Although I do wear skinny jeans and shorts in summer), I would estimate that I am probably most likely to be wearing a skirt or dress over jeans, although I do have a pair of really nice leather look pants too.
Basically as with many - TG women I went through the phase of buying all the wrong clothes, either far to skimpy or too short, but for me the lifeline that changed everything for me was going to a half day session at a Image consultant with House of colour (
https://www.houseofcolour.co.uk/about).
What I came away with was a swatch of my colours, a booklet describing the right colours to wear and how to combine them and even the best colours for lipsticks, eye shadow, mascara, bushers etc that would help to highlight my skin tones. The aim being that when I entered a room or even met someone new, all they would see is a woman with the correct and matched clothes, make up etc.
In fact its interesting how many times I have heard the statement from other women - Oh high nice that lipstick looks on you or what colour and make is that nail polish! Even my beauty therapist notices it. Only two weeks ago she said its so nice to see you and how impressed she is with my colour matching presentation every time we meet! She of course knows I am TG.
This has all helped immensely to me to blend in and appear 100% female. Its interesting but I think the right colours, the correct makeup, obviously no facial hair or little of it, sensible clothes, confidence (and it helps if you no Adams apple and small hands), the right accessories (like a wedding and engagement ring) all helps to present yourself as nothing more than 100% female.
Three incidents amply typify what I mean here. On Sunday I was out with some women friends, both who know that I am TG and they were with two other women that I have never met before. We talked about just about everything under the sun, but eventually the conversation led to children. One of the women asked how many children I had and was my first one a difficult pregnancy. I explained that I couldn't have children then told her that I was Transgender. Her expression was Wow! I would never have guessed!. The second thing was last night. I popped out to Tesco's for some late night shopping. I didn't want to put too much on, so just added lipstick, mascara and eyebrow pencil (ie no foundation, blusher etc). Now my lipstick is one that has been exactly matched to my skin tone (similarly I always keep my nails and toenails perfectly manicured with nail polish on them. In a casual conversation with the check out girl complaining about the miserable weather I mentioned that I had just had 5 glorious days in Marbella. Her comment was I hope you managed to get your bikini on and got some sun. I told I did (although its a one piece!). Finally last week I had a consultation with Facial team in Marbella about FFS. The doctor I saw basically asked what I was doing there as he couldn't see why I needed facial feminisation surgery at all, because to him I looked 100% female - this is all about presentation and the right colour combinations in makeup and clothes.
My strong advice is that if you haven't done it yet - do go an see an Image Consultant and get advice on your Colours and skin tones. I am an Autumn person.
Best
Judith