I mean right off the bat. I found a full Hooded Thalmor set on my way to Riverwood from Helgen but the first set of mage gear you get from the cave is better. --- The real trouble with reality is that there's no background music.
Honestly a lot of the loot is pretty random. I guess the easiest would be to head straight to Whiterun, get a Firebolt spell from the court Mage, and then take the wagon by the stable to Winterhold and join the Mage College. They hand out gear to new mages. --- The secret to life is honesty and fair dealing. If you can fake that, you've got it made.