If you are using Hodgdon's extreme line of powders, the new temp stable Alliant powders, and a few of the other more temperature insensitive powders, I wouldn't worry too much about it. Just don't be pushing it right to max load or over, because then you might run i to some issues when it warms up.
If you are planning on using some powders that are known to have wide fluctuations of burn rate, depending on the temperature of the round, I would definitely reconsider. But that also depends on how cold you are talking, and how warm if weather you will be shooting them in.
I have worked up loads a bit below zero, that shot perfectly in the summer time, with very minimal change. But I was also using H4350, Varget, and H4895. Which are very temp stable powders, depending on the exact cartridge they are shot in, but across the board, pretty stable.
My 300RUM loads with 225-240 grain bullets use 101.0 grains of US869, I worked up in the heat, because it changes quite a bit. Shoots almost exact same point of impact 40°C and -40°C. I do not load for groups at that temp, but I will take a quick measurement of speed and point of impact when I'm going out for elk, regardless of how cold it is outside. Once it gets cold enough, and your bore diameter decreases in size, you will start to gain some speed again, and build more pressure.
And for some reason every bullet over 220 grain just plain likes 101.0 grains of powder. I get a few hundred fps drop in velocity, so only same POI at a hundred yards. And I works great for hunting, and easy to load for.
I would recommend developing the load in the hotter months, then checking poi and velocity in the cooler ones. You can for hunting, just to develop the load around the temperature it normally is around hunting season, and use that load for hunting season. All the ways work, just pay attention to what max load is, and try to get info on the temp stability of the powder you are using.