Remember that in the winter, we are warmer than the air around us, and what we feel as cold is the heat leaving our body trying to put us and the air at the same temperature.
The wind speeds that process up. “Feels like” is the temperature it would have to be for your heat to leave your body that fast without the help of the wind.
A thermometer however has no body heat, so it is already at the temperature of the air around it, and doesn’t go below.
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