I totally feel you on the skirts + bun combo, lol. I feel like I either look really religious or like I'm larping. I don't like how I look with my hair pulled straight back either, but I find doing braid accents (I like lace braids around your hair on each side of the part, I find that softens my square/round face too!) helps with that.
Getting some layers to have loose might help too. You could do wispy or more chunky if you want the "hair down" look. Length is up to you, I know most people recommend shorter ones, chin length and up, but I like the look of longer ones too. I'll sometimes just leave the front pieces of my hair down and even though they're collarbone length and long enough to pull back, I don't think it looks out of place as long as the rest of the hair isn't super sleek.
That being said, if you want to cut back to waist and just wear it down, do it! At the end of the day what matters is that you're happy with your hair. I would take some time to mull it over though, and perhaps try with some layers first - I know for me I often want to wear my hair down but when I do, it quickly gets too annoying. And my hair is just APL!
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