I think I may take a different approach to some styling issues and questions.
I think, why is it that you want to wear that skirt ? That's not a loaded question, it's just a basic question about what draws us to certain items and to create certain outfits. Because then we get to, wear the skirt but be sure it's not twee or do things to mitigate twee-ness. (just using twee as the going term; not sure that's even the right term). So the question is, what kind of look does that skirt help you achieve--maybe fun and flirty? and then you're just trying to line all of that up to the right degree. Why this skirt and not another skirt? Or get the look another way?
Examples would be, sometimes I'm trying an item and I just know it's right, all the way. But then there might be an item that has some very specific features I need, but I'm not sure it checks all the other boxes I'd also like, or how to style so it does. For me, shoes are a good example. As in, these shoes are SO comfortable and "go" with lots of outfits, but...are they frumpy? Or, this longer skirt length is really elegant, but most stylings are shown with heels--if I style it with flats, will that destroy the very look I was hoping to achieve? Or, what features do the flats need to get closest to that look? Or maybe a perfect dress in the not-best color--it might be worth adding scarf or jewelry or topper to make it work.