Is the clutch still kicking on, just not cold?
Is it not kicking on at all?
In either case, check the pressure in the system. If it's converted to 134, a cheap refill kit has the proper connection to check it.
If it's R12, you'd need an A/C gauge set - Harbor Freight sells them - that come with R12 and 134 gauges.
I'm not 100% familiar with these truck's A/C, however; on newer cars, under a certain pressure, the A/C will not kick on. Since temperature affects the pressure, it is possible for conditions to be just right for the pressure to go just below the threshold for a bit.
The line pressure and clutch engagement are the two main things to check.