Body-image shaming is sort of rampant, even if we want to reject it. On some level society draws a correspondence between "being female" and "wanting to look good/beautiful," but what society promotes doesn't reflect your attitudes about gender, and with men increasingly targeted as well, that correlation is only getting weaker... and this doesn't even begin to address where androgynes (a diverse group in its own right) are in the grand scheme of things.
On some level, what we think of ourselves and others involves "filling in the gaps," and sometimes the way we imagine ourselves or others is more "perfect" than what is true. When we see the "naked truth," we can be disappointed. Many countries place value on "making good first impressions" and maintaining those perceptions at gatherings and on Facebook -- we are expected to maintain the image of our "brand" and not show weakness, even when we need help. We lie to each other, but we also lie to ourselves. It would be fine and all, except these pervasive lies inflate our expectations and typically leave us disappointed with the truth and ourselves.
You're not satisfied with the "male" look you have, even though you can "dig" that look in someone else. You've also indicated you wouldn't be happy with a "female" body, although you seem to respect that look as well. You don't sound happy with either appearance, so I think this sort of begs the question: "what do you feel you're supposed to look like?" It's tempting to feel helpless here, but it may be that your sense of self dictates wearing clothes to your liking. For example, earrings are not a "natural" part of the human body, but some people, regardless of their gender, feel they are supposed to wear earrings, and in fact they need to wear certain types of earrings to feel complete/true/assembled. People in most developed societies are so used to wearing clothes and seeing the particular aesthetic that wearing nothing can take them out of their comfort zone, and you may be in the same boat -- and dresses/skirts are simply the clothing options that deliver the most satisfying expression (just as certain people need certain earrings and hairstyles).