I'm not an expert on this at all, but I would say to wait until April time and the beginning of the growing season. I am waiting myself as I want to grow an oak tree or two. I've tried already but have little hope that they'll grow. Good luck and I await contradiction of my answer by someone better informed.
I'll give that a go after I've planted the cuttings but will have to wait now until autumn to collect the acorns. Things take a long time in gardening, not sure if I have the patience!
You can propagate cuttings at any time of year as long as you protect them eg. gardeners "come out of hibernation" from February onwards and start planting seeds etc. but usually under glass to protect them from frost. So as long as you can protect the cuttings from frost/rain/snow etc then you can plant out now. ps. don't forget plenty of root powder. ...and in answer to the acorns, Jonathan R - acorns (like horse chestnuts which i try and grow) are hard to get to grow as you don't know which ones have been pollenated (in the sense that mummy and daddy have got together - if you know what i mean) so the best way is grab a large handful and plant them out (spring time is best but not essential) and by the laws of randomness some of them should grow. They're very hardy so you don't have to worry about frost etc - plant some outside and forget about them for a year or so (if you're low on patience!)