La Canadienne. They're marketed as being snow-tolerant but I live in a city that just gets rainy in the winter. Many dressy boots, even those made from quality leather, get worn-looking when worn outside in the rain which sort of defeats the purpose. My La Canadiennes have kept going - and looking dressy - season after season with regular polishing and minor repairs. Unfortunately many durable features popular on long-lasting masculine shoes like Goodyear welts just aren't considered appropriate for a dressy, feminine pair of heeled boots. La Canadienne boots may be over $500 new and full price but I often find new pairs available on some sites for as low as $200.

High quality shearling slippers. Teaching requires a lot of time on one's feet and having something nice and comfy to slip on after work that regulates temperature is nice.

Setting aside space for, and getting started on (the idea is you continue with a lot more of her input) an ergonomic work-from-home space for her to use as needed. People don't often realize how much work teachers have to take home and as home is not seen as the primary work location they often will work at the kitchen table, couch etc which causes back stress and so forth over time.