Interesting post. You've made suggestions for which I've tried variations for the last 15 or so years.
I don't dress as a woman, but it's not a lack of courage. It's a lack of interest. Everything I'm wearing right now comes from the women' departments of various stores. But, I have a full beard and hair down to mid-back. I have no desire to lose the beard or look like a woman. I love wearing the things I wear. I have tried the many/most of the various alternatives you mentioned and keep coming to the conclusion that the alternatives are not the same and don't fill the same need.
I do have both men's and women's skinny jeans and wear both openly.
I've been wearing a bra almost daily for the last few months. I don't to forms and buy 38 or 40 A/AA and use extenders as necessary. The color isn't so much of a concern and I try to wear shirts that hide the lines of the band and straps. Wearing a bra makes my itty-bitties feel special and I've gotten to the point wear i don't feel completely dressed without the feel of the band around my chest.
I have sports bras and bralettes but prefer underwire bras and the way they shape my natural breasts just a bit.
I actually think that it's maybe more challenging to be a man with an openly feminine presentation than to be a man presenting as a woman. Even if one doesn't pass, at least there's more of a disguise or camouflage to one's identity. With my long hair and beard, I have a very distinctive look in male or androgynous mode. The few times I've been out in bearded crossdresser mode, there's been no mistaking who I am.
I do wear 4 and 5 inch inseam men's shorts in warmer weather, which was the norm back in my twenties but is considered to be feminine now. I have a fair number of pink t shirts and button-ups. I also wear various necklaces and a stack of bracelets most of the time. I am trying to work up the courage to wear pearls in male mode but not quite there.
I have one pair of men's Under Armor compression pants that look no different from the black yoga pants/leggings that I've begun wearing to the gym for the last few weeks. I wear the man's compression pants and women's yoga pants alternately and basically ignore other's reactions. I've even ventured to Walmart after a workout and run a couple of other errands dressed like that. I do wear unisex t shirts that are long enough to avoid offending the sensitives out there.
I like both. I like having shaved legs and I like the process of shaving. I just wish I had more time before the stubble got uncomfortable. I'd love to remove a large portion of my body hair permanently but I'm not willing to spend the money on that.
I like wearing a bra and I like the act of putting it on and taking it off. If practical, I almost always remove my bra with my top still on. I have no idea why that so satisfying, but it is.
I love the routine of putting on mascara and eyeshadow in the morning. That's one thing that I think the process is even more enjoyable that the result. If I do it right, the makeup is almost undetectable so it's not a visually exciting thing. But, putting it on satisfies something in me and then just knowing that I'm wearing satisfies something else in me.
I don't wear pantihose often, but I've begun to wear nude knee highs with my men's or women's jeans or leggings. I've gotten to be completely comfortable wearing them instead of socks. But I also like the act of putting the knee highs on, especially when my toenails are painted.
For most outerwear whether it's a dress, athletic wear, shorts or whatever, it's more the result than the process. I like looking in the mirror and finding that the femme things in my closet or drawers suit my preferred aesthetic perfectly. I don't get anything like that feeling from seeing myself in men's things, even if those things are less traditionally masculine.