I am very similar to Suz.
(Suz, by the way, about that skirt: don't forget that cuts are slightly different nowadays and that might play a role too in your recent dissatisfaction with it).
All my life, I have struggled with fit. In my younger days, mostly, clothes wanted to escape me, blouses gaping open, cami escaping, bras impatient to peep, pants slumping no matter what. That's because fashion was on the max side, while I was not, and my tiny wallet hadn't discovered a good tailor yet.
I was throughout my 30's and for a good part of my 40's a slim inverted IT with -strangely enough - pear tendencies. Athletic wear fit me well and, for once, remained on me with enough sturdiness and reliability. I was a young travelling mom on the go, so I was content with this generic look.
In my mid 40's, my body was still very much IT but slowly morphing and it got to a point where I thought I was going to become an apple, because it seemed I had less and less hips, while retaining a shapeless mid-region and increasingly muscular shoulders.
Now, soon to be 50, I am moving towards what I hope is a more hourglass figure. An oddity: by gaining a little bit of weight and muscle around my hips, I suddenly have more of a waistline! Which is a good thing in terms of dressing. I realize that some things that didn't suit me before now look better because there is mass there to hold it up if you will. For example, my fit in most jeans is easier (especially cigarette cut), it makes more sense right away when I put them on. I guess it's because there are some hips to fill them out.