We may be living in the best age for long-hair on adult women (at least in the USA) since before the 1920s, with the possible exception of the 1970s.
I wasn't around in the 50s or 60s, but I don't see long hair in movies, modeling photos, or family photos. The 70s looked pretty good through the lens of time -- e.g., Katherine Ross in Stepford Wives.
In the 80s, from what I can tell and partly remember, were not a time for long-hair. Women felt that the should permanently cut their hair short usually by age 30 and definitely before age 40. Long hair was seen as unprofessional. Even unpermed shoulder-length hair was super rare. Buns, which are necessary to make very-long hair practical, were seen as an old-fashioned relic of the 1910s.
Things got better in the 90s. I'll never forget the first few times I saw a women wearing a bun in public. That was the sign long hair might come back.
Now I routinely see women in their 20s, 30s, and even 40s with mid-back length hair worn down or in various styles, including buns. Waist length is less common but not rare. Sure, classic+ is rare, though it may be more common than it seems if hidden in buns.
In terms of "solutions" to make things better, I'm not sure.
Certainly respected high-profile people with real natural long hair help. I think it's wonderful how Chelsea Clinton is wearing her hair at age 44. (look her up if you haven't recently, regardless of your politics.)
I think it would help if women felt very-long hair was worth trying once or twice in their life. If the stigma of wearing long hair as a professional woman in your 30s or 40s has gone away, there's a chance for women to grow their hair out to waist+ a few times even if they like to change it up and go short too.
I've seen a few examples online of women who committed to not cutting their hair until a particular milestone: finishing a doctoral degree, getting into med school, or getting married. These were amazing rapunzels with healthy knee+ length hair who started their journies from ordinary lengths. If that could become a trend, it would be amazing. Unfortunately none of them were American.
A woman growing out her hair significantly in college or for her wedding increases the long-hair population. Some might realize their long hair is actually easy to maintain and keep it. Even if they don't keep it long-term, they might influence others to try long hair and help the trend.