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My preference is for women to have some length to their hair. So instead of a very short hair cut, maybe something chin-length, for a woman who prefers short hair. I think hair that has a bit of movement to it looks younger and fresher. There are a few women who can look very feminine with a very short look, but I think these are in the minority, and even then, they will look even more feminine with a bit of length.
Of course ultimately it comes down to personal preference. Some women simply are not as concerned about how others perceive them and more power to them if that is the case. Others don't prioritize their physical appearance, and again, that is certainly their prerogative.
I am in my 40's and have long hair, but what I have found is that wearing my hair super-straight looked good on me 4-5 years ago, it now is not as flattering. I find having loose waves or curls with more volume looks better now. Luckily I have hair that can go either way, so I can do that if I want. I like to wear my up in various styles, so that is another reason I prefer to keep my hair long.
With short hair, I would need frequent hair cuts and daily styling since my hair is thick, so I feel that longer hair ultimately requires less maintenance than short would. So I doubt I will ever have hair that is shorter than shoulder length. I would always want to at least be able to pull it back into a ponytail when needed.
I have an older friend who is about 60yo. She had pretty short hair when I met her, but has since grown it out to the point it is almost shoulder length, and it does make her look younger.
I like shaved heads, but you have to have the right shaped head for it. It is just not for everyone.
I like women who wear a long hair and like a shave head for a man.
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