I wear most of my maxis year round and while this Joie dress is very summery, a thick wool sweater and some boots with serious tread help it transition into early winter. In the summer I wore it with some flat form sandals and a denim jacket - for winter I put a thick wool sweater over it and then a jacket wth a high percentage of wool and a scarf to help hold in the heat. When the temps drop lower I will wear a longer wool coat to really stay warm. I wore Dr Marten's Persephone boots with it, these are roomy enough I can wear two pairs of warm socks and they have an aggressive tread for walking on icy surfaces.
I personally like more of a cropped sweater, as you can see here the waistline makes a big difference and I usually go with a higher rather than lower waistline.