Things to consider when calculating "cold" tire pressure.
Is your bike in an attached garage? The temp in the garage will be warmer than the outside temp in the winter and cooler in the summer.
Is the sun shining on your tires? The sun can rise the temps in your tire by a few lbs. Ideally, the tires would be in the shade before checking them so consider that when taking pressure readings.
General rule is 1 lbs of air pressure for every 10F of temp change. That means a 10F temp increase = about a 1lb increase in tire pressure. If it is a really cold morning but I know the temps will be significantly increasing later in the day, I'll take that into account. So if it is 20F in the morning but I know the temps will be increasing into the 70s (an unusually large temp spread), I'll let my tires be 2lbs (~5%) under my target pressure in the morning to help offset the +5lb natural pressure gain the tires will see throughout the day. A few lbs +/- isn't gonna make a huge difference in wear/performance. The important bit is to keep an eye on them and actively manage them so you don't unknowingly wind up with under inflated tires. I believe the NHTSA considers a tire that is 25% below the recommended cold pressure as under inflated.
I keep my pressures within 1 lb of my target. Managing this is made easier with an on-board TPMS with real time pressure readout.