Not sure what you mean – that’s not really familiar to me at all. The one scenario I can imagine is the following: you’re outside, where it’s very cold, but lightly cloudy or even sunny. You go inside into an unheated building. The air temperature will be the same as outside, yes. But outside, you were getting hit by the rays of the sun, which carry energy and warm you. Inside, you are not, or less so, so you feel colder. You’re basically stepping into the shade, which works no matter what the temperature is.
You cant feel temperature directly. What you feel is the heat exchange from your skin. Temperature is the most important factor in that but not the only one. Humidity is another big factor. Air movement is also one.
Another thing that is unrelated to what you feel on your skin is that you will feel cold when you get sick ie the common cold.
Both explenations are equaly possible especially in winter.
Humidity – for instance I live in SE Asia, where there (often) is very high humidity. So 35°C here feels a hell of a lot hotter than 35° in for instance Europe, middle east, or other drier places. Has a lot to do with your ability to sweat properly – thats really the only way your body can regulate temperature down. So when its very humid, there is already so much moisture in the air that you struggle sweating as well as you would otherwise. So 45°C can kill people in Bangkok – but be “just another day” in Dubai. Its ofc very hot in both cases, but feels very different.
Same with cold. -30°C in Northern Russia isnt *that* bad – its cold ofc, but manageable. -30°C in London, and birds starts falling from the sky.
Trying to keep this simple, in addition to humidity (convection) we also radiate heat. This can be felt if you stand in front of a window on a very cold day, you can feel this radiation. You notice this in front of the window because there is a sudden change between the rest of the room and that location, but this exchange happens wherever there is a temperature difference, so even if the air temp and humidity were exactly the same, you would feel colder in a room with cold walls.
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