Hey Darrin,
DISCLAIMER (for anyone who will read this and think it "harsh"): I don't often post in the "do I pass" threads (nor do I post looking for feedback) because I find that most people are far more "Pollyanna-ish" than I would be, and I don't want to be a total downer ->-bleeped-<- for someone, nor do I want sunshine squirted up my own ass.
But since you asked for the feedback and don't seem to take offense at bluntness, I'll give you my honest assessment, as I struggle with this one too, at least with the hair. Luckily, I have a great hairstylist (and there's another stylist there, a gay man, who also gives advice) who's very up-front with me about what I can and can't pull off, and what says "butch lesbian" vs. "gay man."
1. Hair - the first two photos have all your hair oriented upward. It seems that when I have the hair all pointing up like that, I tend to come across as a BL vs. a guy. It's different from when I do a fauxhawk or the little "ducktail" thing that's popular right now (at least among many gay men I see). Maybe consider side parting or something different like that? I think the last pic is best as far as hair goes. But you're still being held back by...
2. Flannel/plaid shirt. Screams "lesbian." When I decided to really put effort into passing, I had to give up a bit of "but it's comfy!/but it's ME!" and I had my little hissy fit about it. But right now, it matters more to me to be seen than to be all 90's grunge rocker in my comfy carpenter cords and my flannel shirt. :/ You may have to make a similar call. Seriously, it's part of the standard uniform. Lose the plaid.
3. Oversize glasses - emphasizes being too big for your face, emphasizing face, and you know where this goes...our soft, delicate features, etc. (ugh). People have already mentioned the glasses so I'll just add that I second the idea of smaller ones and/or different style.
4. You appear stocky/overweight in your photos (but the angles are tough so if you're actually not, ignore this part!). Putting on extra fat will often accentuate facial fat for us (as SOON as I start putting on extra fat, it flies right to my chin), which will impair passing. It also pads the hips and ass for us pre-T folks. And, for whatever reason, it seems to be a common build for butch lesbians. I don't know why. So if you're willing/able (I don't know how much is fat and how much is just "naturally stocky") to lose some weight, at least in fat weight, that might help. I went from 147 to 132 when I finally realized that I wasn't appearing "big" to anyone, just fat, and it helped my passing ENORMOUSLY.
The last thing, which you can't do anything about, is that you just happen to have nice thick lips, which are generally much more common on females than males. You're stuck with that and maybe later it'll even be an asset, but for now it doesn't help. :/ I have the same attribute.
Hope this helps,
Eli
