My easy formula to continually use a shift dress all year is adding some layers to make it warmer in the winter. Most shifts can be worn year round, although I keep the wool just for the winter. This also helps be justify purchasing yet, another, dress. I really don’t need it, but, I can wear it all year, therefore, decision made (and cost justified).
For your upper half, a classic white button down is almost fool proof in every case, or, a turtle neck can, often, work as well. The key is that you want to add some type of sleeve.
For your legs, tights (I go with a heavier version, like these) to give an extra layer on the legs. Using a knee high boot can also provide a layer of warmth, or can be paired with booties.
Shoes: Above: Michael Kors Becky Slingback; Below: booties old, similar here and here; Top: Old, similar here; Dress: Banana Republic Bow Neck Ponte Sheath Dress