In colder temperatures the Tesla Model Y will lower the displayed % state of charge, especially overnight, by as much as 3% to compensate for the colder temperature. The displayed estimated range should also be lower by the same amount (3%.) If you drive the same route at the same time of day the variables would be weather (including wind, precipitation and temperature) and traffic.
You can use the Wh/mile readout under the Trip odometers: current trip, since last charge, Trip A and Trip B as a gauge of your winter driving efficiency. After several thousand miles your lifetime Wh/mi will be consistent. Your Wh/mi for the current trip or since last charge will be higher in winter. In WI probably 20% to 30% higher. LPT: Rename Trip B to Lifetime and don't reset this one.
The estimated range display by the battery indicator is not as accurate as the Energy Screen metrics. The range display does not factor your speed, only the posted speed limits. The Energy Screen, while driving along a route using the Navigation system will factor weather conditions (including temperature, wind and precipitation), traffic in metropolitan areas in addition to elevation changes for the route and your driving speed. In general you can trust the information displayed on the Energy Screen including the estimated remaining battery charge when you arrive at your destination or next charging stop.
LPT: If you are concerned about reaching a destination with the current battery charge start out driving at or below the posted speed limit for the first half of the trip leg. Let the glide slope displayed on the Energy Screen be your guide as to your energy consumption and range or need to stop for a quick charge. If the consumption and range look good at the halfway point then gradually increase your speed if you want.
Above 60 MPH you can improve your efficiency and range by almost 10% for every 5 miles per hour you lower your speed. 10 MPH slower nets almost 20% increase in efficiency and range. Slowing down is like having a built-in battery reserve.
The seat heaters and steering wheel use a small fraction of the energy used by the heat pump. If you are at the point on a trip where you have range anxiety even after lowering your speed cycle the climate control off and on (so the windshield, windows don't fog) and use the seat heater(s) and steering wheel heater to stay warm.