Goodness me, @AppleDumplings - how have you managed to make 5’9 and hourglass a problem?
Firstly - burn the white plimsolls and denim jacket - they’re holding back your thinking.
Take a look at this dress:
MaxMara wool
The model is apparently 5’10. Clearly her other measurements are smaller than yours but there’s absolutely no reason why anyone (up to a size 14 here but a million other examples are available in larger sizes everywhere) should not be able to wear this type of dress.
You’re presumably shopping for autumn? There isn’t a single type of boot I can think of that wouldn’t work with this. Knee high, mid-calf, ankle, pull on, laced, zipped. Purple suede, silver foil … (I’d stick to black or brown leather that can be satisfyingly polished for years.)
It doesn’t need a belt. (Though some people might wear it with one.) You could load it with jewellery or wear it unadorned. With a thin t shirt or shirt beneath, or a huge chunky cardigan above. It will look fabulous with a winter scarf. You could try it with your trousers.
There may be reasons why you won’t want to try this dress. Cost, woolliness, colour, exact sizing, general trepidation. Find a different version if you like. But I can’t think of an easier dress to wear.
(I am of retirement age, though not, and ruthless about my wardrobe.)