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Transitioning Your Look: A Postponed Adolescent Experience

A reply to a question from a trans person wanting to get their hair dyed:
I have a few trans friends, and every single one of them colored their hair dramatically at some point early in the transition / living out as a woman process. I never would have told them at the time, but to me it always called more attention to the fact that they were trans and detracted from the "passing" because it looked like a costume they were trying on instead of just being themselves.

It's like they were going through the teenage girl process but as much older women, which I TOTALLY understand, but it wasn't exactly doing them any favors. -- Source
There is a lot of truth to the idea that gender is a social construct. For cishet individuals, dressing like one gender or the other and "passing" for one gender or the other is rooted in a literal lifetime of being trained in how that gender is supposed to present itself for a particular culture.

Another phrase from a different reply to the above question is the culture of femininity. The MtF trans individual was trying to cross a cultural barrier, trying to move from a culture of masculinity to a culture of femininity.

Gender presentation is a kind of culture within a culture. Historically, there have been very big taboos on crossing the invisible barrier that separates the two. It's still a hot button issue, but not as drastically as it once was.

But the point I want to make is that even when someone is cishet and has been trained in the culture of their gender from birth, they typically transition from childhood to adulthood via an awkward adolescent phase. Their body is changing and their role in life is changing and they try various things out that often don't fit them especially well, both literally and metaphorically.

You may need a lot of practice before getting your look right. You shouldn't be too hard on yourself.

You also shouldn't immediately assume that it's the fault of your body. It may be due to being left out of the culture of feminity/masculinity for so many years.

Don't expect to get everything right on the first try. No one does, not even the people who were raised in the gender culture that fits their gender identity.

Try to set aside time for trying on a zillion outfits, trying out different hairstyles, etc. Try to find ways to try things on for size temporarily first in case you don't like it. For example, a wig or temporary hair dye instead of a drastic hairstyle or permanent hair dye can let you try it out without committing to it.

But also remember that if you do cut it or dye it and it goes badly, it will grow out and you will get another chance. Having a dreadful haircut you hate at least once in life seems to be a very normal experience the world over.

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