For many transpeople born male, they think the name of the game in looking like a woman is to wear clothing assigned to women in this culture, preferably with a body shape that is as femaled as possible, either with shapewear or from the inside.
This is looking like a woman to them.
For women, though, looking like a woman means something very different.
Women are creatures of connection, always scanning their environment for clues to what is going on around them. We notice differences quickly, always multitasking and having an eye out and an ear cocked for changes.
To be a mother you have to look out for the welfare of your family, knowing when there are threats around, seizing on opportunities as they come by, and catching the gleam of possibility to make things better with a adjustment in stance.
Living in a world of men, your strength doesn’t come from size or force, rather from wit. Seeing what is going on as early as possible allows you to adjust your approach, tailor your choices to make a difference.
Looking is the power of a woman, even catching the flicker of emotion before another even knows that they are having one. Looking close allows us to build models of our world and the people in it, anticipating reactions and shaping strategies to get what we need and want, for ourselves and for our families.
The better we look, the better we can choose our battles, winning before others even get their hackles up.
The high school experience that sets much of the pattern for how women interact is a place to be trained in looking well, seeing the ebbs and floes of those around us. There is a reason chick flicks tend not to have big action scenes, because to women looking at people engage emotional situations is usually even more dramatic than another staged petrol bomb.
Looking like a woman means having a powerful sense of the forces at play around us. That understanding allows us to play into those forces rather than just playing against them, brutish and bull headed.
Every woman wants to look good, of course, but the way she manages that is to use her looking to assess what kind of looks will suit her and the situation. Because she has been looking at other women her whole life, building a vocabulary which lets her code, understand, and store looks. That vocabulary is hers to assemble looks for herself and to understand what other women mean by the looks that they create.
Looking like a woman starts not with padding and makeup but rather with context and understanding. You learn to appreciate choices that you would never make for yourself but which work well for other women, learn to be effective in the world, and learn how to assemble looks which work for you.
It starts with the senses, this looking like a woman, not with the clothes.
Linda Lavin sings about looking like a woman at other people in this song from “It’s A Bird, It’s A Plane, It’s Superman”