Use 10W30 as an example.
Looking at the second number first, we find that the 30 means that at 100c (212f) the oil's viscosity is between 9.3 and 12.5 Cst (a measure of viscosity or thickness). 0W30, 5W30 and 10W30 are ALL in this range at this temp. A 20 weight is a little thinner at 100c, a 40 or 50 weight is a little, or a lot thicker, again measured at 100c. (Remember, we are looking at the SECOND! number only)
The first number is read 10 winter, NOT WEIGHT!
It is an arbitrary value THAT IS IN NO WAY! comparable to the second number. The 10 means that the oil is borderline pumpable at a temperature of -25c (-13f). Comparing other weights, we find that a 0W pumps at -35c (-31f), a 5W pumps at -30c, a 15w pumps at -20c and a 20W pumps at -15c.
Oils must pass some other viscosity criteria as well to obtain the various W designations, but in general terms the lower the first number, the lower the temperatures at which the oil can flow and pump.
So... if it gets really cold, use a 0w. Kind of cold, a 5w. Not too cold, then a 10w.(or 15w, or 20w)
Hope this helps a little...