@Captainobvious35 I've done a quick moodboard for the skirt as I think this is probably the trickiest one to style up. Black and cream would be the obvious choice for this time of year as it's a strong, bold colour. I like the more casual look with a roll neck and boots but if you wanted to dress it up, I'd wear with a black top with some kind of neckline interest such as this sweetheart style top from H&M. If you're into prints and a bolder look, I think it would look great paired back with leopard print or something like this ombre top. For a going out look, I'd wear with heels but for a more laid back look, I'd pair back with a burgundy boot to bring all the gorgeous earthy tones together.
I agree with you on the jacket, the jeans would look too matchy matchy if they're the same tone/ wash. An all black outfit such as this dress would be an easy option but I'd also like to see it with winter whites- think ecru jeans and a nice roll neck underneath paired back with black boots. It would also work with leather trousers, a smart top and boots for a dressier look.
I have a pair of white boots and I actually find them really easy to style and they add an edge to any outfit. They go with anything really as they're a neutral- blue denim, black, brown tones. I've got a rixo zebra print dress that I always wear mine with- they just lift the outfit whereas black looks a bit boring and safe. Another idea would be a black satin midi and cream top, sticking to a monochrome look or even bringing in a pop of red would look lovely.
If you're happy to play around with colour, you could wear them with the orange skirt. Hope that helps