A point about make up and presenting outside.

[JMJW]

So put my make up on and contour a feminine shape as best I can.

I look in the mirror in my room, looks  good acceptable in daylight and in room light. Feeling confident enough to go out.

Then when I'm walking, I see my reflection in car windows or the windows of the bus, or the windows of a building. The  reflection this time keeps the dimensions of the facial features, but desaturates and washes out the colour of the make up by nature of being a dark image. Look good I do not!

I feel my confidence draining away. Has anyone else noticed this effect?

I'm looking for a way to find a decent look with minimal make up, but it's not working out. 
It's fun to try though.

[KathyLauren]

You can't really go by the reflection in a window.  As you say, plain glass washes out colour and doesn't give an accurate picture of what you look like.  The daylight image in a proper mirror is what you look like.

Confidence comes from repeated practice.  Just keep doing your face and going out as you.

I sometimes do makeup, but mostly, for grocery shopping or taking the cat to the vet, I just put on a bit of lipstick and mascara.  It takes all of 15 seconds.  Today, I was out like that, with the addition of a two-day growth of stubble on my chin in preparation for electrolysis tomorrow.  I don't let it get to me.  I put some effort into other areas of my presentation - clothes mostly, my hair (a wig), and I try to get my voice right - but ultimately, I yam what I yam: a 62 year old trans woman.  I am out of the closet, I like the way I feel when I am dressed right, and I feel good about myself.  Anyone who doesn't like it can get out of my way.  I learned that just by doing it every day.

[JoanneB]

Like KathyLauren mentioned, what is doing the reflecting can and will alter the colors. Also, there is the type of lighting you used when applying the makeup. The color temperature of the lights will make a BIG difference in daylight. Having a nice big window with lots of natural lighting is a big plus. Nightime lighting is "artificial" by it's nature so what you see at home is usually close enough except for like a brightly lit store.  And then, there is the angle of the lighting on your face.

Practice, practice, practice. In the beginning I think there were times I needed to wash everything off and start over 3 times, twice a lot more often.

[Dena]

Lighting can really mess up a good makeup job. Under incandescent or some Led lighting that's deep in to the red end of the spectrum, my hair appears light brown. In sunlight or fluorescent my hair goes gray. Because of this, I hadn't realize my hair had gone gray for a long time as the only mirror I used what in the bathroom with incandescent lighting. It took a DMV photo to really drive the point home and while I know the DMV is known for taking bad pictures, that was the worst.

[Jenny94]

I have noticed this effect too. But I think honestly, a lot of cis women will look like men in a reflection in a car window...I've been learning recently to stop looking at my reflection and just practise my body language. Also, I found it helpful to do a study of women's faces with masculine features, and vice versa - I can post the list of celebrities that I made if you're interested - to give me confidence. There can be a really fine line between a man's face and a woman's, and make-up is essentially a detail that helps to give us confidence. =)

[JMJW]

I'd like too see some examples from your list for sure.

When I said minimal make up in the OP, I'm trying without any sort of base like BB cream or foundation for when I go to the gym etc. Without lipstick or eyeshadow. Really limiting it to eyeliner, colour correcting my 5 o clock shadow, lip gloss and mascara. It is more difficult to  pull off and have self acceptance with the result, more so than a full face.   

[Jenny94]

Great. I have a similar 'minimal' routine, though I can't really call it a routine at my early stage: just bits of highlight and blush here and there, pencilling in my eyebrows a little and then mascara. Foundation is a bit of a ballache. Tell you what, I'll just control C&V the list I made -

LIST OF BEAUTIFUL WOMEN WITH MASCULINE FACIAL FEATURES

Lake Bell
Barbra Streisand
Claudia Black
Liv Tyler
Julia Roberts
Cate Blanchett
Idina Mezel (nose and jaw)
Nicole Marrow (jaw and cheeks)
Lady Gaga (chin, nose, forehead, amount of empty space in her face)
Glenn Close (seriously, how is she not trans)
Tilda Swinton = David Bowie
Florence Welch = Noel Fielding
Nicole Kidman (forehead and size of face)
Cher!! Feminine chin, everything else masculine.
Wendy Williams (without make-up, could easily be a man in a wig). She said, "There's no worse way to insult a woman than by saying she looks like a man, but once a woman gets over that, there is no stronger woman."

[Ashley3]

So put my make up on and contour a feminine shape as best I can. ...  when I'm walking, I see my reflection in ... windows ... The  reflection ... desaturates and washes out the colour of the make up by nature of being a dark image. Look good I do not!

Obviously you know, windows aren't the best mirrors but even the best mirrors can be deceiving when trying to assess what others see. If you're walking and looking in windows, my guess is you're scrutinizing yourself much more than anyone else will in a window reflection such that you may be seeing a perspective that isn't realistic for what you're trying to assess.

Self-assessment of appearances, beauty, and femininity is a hugely tricky business for anyone generally but for the MTF I feel it's compounded. So much plays into it... one's current mood/perspective, one's ability to use their own eyes to see as others might see, a feat that so far seems largely an impossibility when analyzing the self. I even feel the human mind sort of positively embellishes "bathroom mirror" and other assessments... I don't know why... probably evolution's protection which boosts our ego by hiding details... if we look in the mirror and don't see the faults, we have more confidence which, at the end of the day, may have been (seems to actually be) more important than aesthetics (though we know aesthetics play a role in mate selection... I most definitely no little about evolution so forgive me dear scientists if this falls short). I don't know... the caveperson who felt he/she looked great in the pond's reflection that morning perhaps caught the most food that day or something... LoL     

Despite all that I feel with effort one can get closer to doing it right than otherwise.

Once one has some level of grip on how others may perceive them it seems a whole world of things can positively/negatively affect things... you have inside/outside lighting... the sun is a light like no other... even mood and confidence can affect things, for certain... and as you point out, all of that can further affect your confidence, further affecting your perceptions... it's like a snowball. I feel the snowball can go either way... toward healthy strides/healthy reconciliation that does not affect defeat, or defeat and confidence that has one stopping from making efforts.

I used to agonize trying to get a hold over where to start and how best to see things—this gave me appreciation for what ciswomen probably grow up learning here/there, much probably from good nurturing little by little over many years. Many MTF transitioners on the other hand are microwaving decades of experience within a few years.

For myself personally, I won't say I've mastered anything by any stretch, but I've made some strides, I've reconciled a little bit, and I continue to not give up trying to go further here/there (i.e., pick a day... not every day... but there are days where I just have a little session to try to figure something out, make it a little better).

... colour correcting my 5 o clock shadow, lip gloss and mascara. ... It is more difficult to  pull off and have self acceptance with the result, more so than a full face.   

When you color correct your shadow, does it really make the shadow go away? If not, that's an area you might want to  consider improving... in person, people will see shadow right off.

I agree with you that it's hard to pull off... when I first started taking transition steps, hair removal... I was ecstatic about full facial electrolysis because I really wanted a normal gal day routine for the face, with light foundation... it bugged me to wear heavy cover... with heavy stick, I felt like I was getting ready to go onstage or something... drove me batty... I was like I wanted my light Mac and just to be normal in that way... I really feel facial hair removal is 'The' only way to do that right. I could be wrong... I don't have data to convince me otherwise... but maybe there is a good light routine to cover shadow... I felt even with the cakey stuff, shadow showed through or it looked like a lot of effort to cover or some such... I just had to get the hair gone... and it went... that's not for everyone but it's my experience so I offer it fwiw.

I realize this thread isn't about hair removal but I'm guessing you have quite an elaborate cover routine to hide shadow and that will show up on the radar unless it's a dark nightclub or something ... maybe there's a way to avoid it being obvious but I was never able to do it... I always felt it looked like I was covering shadow. The women I see everyday do not have loads of shadow cover... shadow cover and a light routine each look vastly different... I think this is exactly what your pointing out, correct me if I missed something... but I get that, went through my version of dealing with that.

[JMJW]

The colour correcting isn't a huge problem as I have brown skin which isn't that far from the orange I use to cover it up. I simply look very manly without make up but really feminine with full make up. It always requires a big make over in order to feel confident enough to go outside in anything but male presentation, which even then I cover my head with a hood.
https://www.pinterest.co.uk/pin/344947652701783504/ So when I go minimal it still looks very masculine.
Its what keeps me from going full time, as full make over
https://www.pinterest.co.uk/pin/344947652701281611/ takes hours.
I'll get there though. I'll do something that works. 

[Sophia Sage]

I found that facial surgery corrected the problem most effectively.  No makeup required.

[JMJW]

Out of curiosity, do they do FFS on pre hrt candidates or do they have a minimum time you have to be on E.

[CarlyMcx]

According to his website Dr Zukowski has performed procedures on crossdressers.

[Sophia Sage]

When I had mine done many many years ago, all I needed was a letter from my therapist.  That was with Meltzer.