Riding boots are a go-to for sure! If you invest in a truly good pair, they are warm and very durable. You can wear them in rain and snow and they will wear very well.
A close second are lace up boots. For me they are a little more casual than riding boots (I just think riding boots are a little more polished.) Similarly to riding boots, they are great with skinnies and leggings.
If you are going for a more dressed up look, I think ballet flats are best. I would not wear heels out when it is wet or icy. Simple flats will look great and can keep your feet wet if they are a good and sturdy material.
Those are my picks and really all I wear in the cold months. Have a great Friday, I will have my TGIF pins up in a few hours. Got to get through Italian first!
What shoes do you prefer in the winter?