Alright you've got my interest.
If your going to do it you might as well get off on the right foot. Now first off the wild populations of guppy have a much greater genetic variation than what is currently in aquariums. Even feeder guppy's have very little genetic variation in them. So your going to have to improve the genetic variation in you initial population. There has been some research done that shows that some strains of guppies can tolerate cold temperatures (55F) and other die quickly. I just read the abstract because I'm not paying $25 for the 1990 article from research done in Japan. Since I have no idea what strains have the tolerance and what don't, the key is diversity. Go to as many stores and buy as many different looking female fancy guppies as you can. The more you can find the better.
Next see if you can get feeder guppies from several different sources (males only). Again the more differences in their appearence the better.
Put the female fancies and the male feeders in your pond together when the water in the pool is at least 75F. Then let the fun begin (a little mood music won't hurt).
After 3-4 months when you have a ton of babies in your "pond", remove the original males and females. If you pick up some fancy males and have a spare tank available you can keep the fancy females that you like best inside. Then let nature take its course for the next few months. Hopefully you get at least 1 more generation before the water starts to cool down. At this point you will probably have a pond filled with all sort of mostly ugly fish.
Now when the weather starts to cool and the average temperature in the pond starts to drop carefully monitor the pond. Remove all of the fish that have died so you don't get an ammonia spike. Once you have lost 90-95% of the population bring all of the females inside and hold in a separate tank from the fancy's. Leave all the males in the pond. If any of the males survive the winter Eureka!! You've got your cold tolerance source.
Now during the second year let the females that survived the cooler water and a few fancy females into the pond with the male that survived. If no males survived the winter just toss in a few different types of fancy males into it.
Then let nature take it's course over the summer and allow the die-off to happen again in the winter. Repeat with taking in the 5-10% of the female survivors to overwinter and allow the males to take the harsh weather. Repeat this for 2 or 3 more years and you might have some very good looking hardy guppies.
I see a few flaws in this plan, the 2 biggest for me is that you can't have 90% of the population of guppies dead with no ammonia (remember this is a low maintenance "fun" experiment, with no hard WC labour), and the most important to me: the sheer loss of fish. The OP's plan was to wait until a few died of the cold, and then bring them in. Your plan has almost all of the guppies dying of cold. By the time there's only a few left, they'll probably be on the verge of death, and you can't take them from freezing water and dump them into warm water.