Problem being, your Animal Companion is an animal. Giving it intelligence breaks whatever connection it has to you as an Animal Companion, so while Headband of Intellect and Pearl of Speech will certainly allow your Companion to use non-passive magic items...
Hmm ... I know that if you Awaken an animal it becomes a magical beast and it cannot be an animal companion. Though [MENTION=98644]Jacob[/MENTION] does raise an interesting point. At what point does the bond break?
I don't know that magical Intelligence boosts break the Animal Companion bond. I do know that Awaken specifically breaks it.
Bearing in mind that I hadn't given this even a moment's thought before Friday (when I read this thread)...
My take on it would be to apply the rule in the 3.5e MM (and/or Pathfinder's Bestiary) than "no creature with an Intelligence score of 3 or higher can be an animal"
last.
So,
Awaken turns the creature into a Magical Beast (and so breaks the Animal Companion bond) and then raises the creature's intelligence. Conversely, a
headband of intellect (or the now ironically named
fox's cunning spell) don't change the creature's type. As such, although they should raise the creature's intelligence, they quickly hit up against the ceiling imposed by its being an animal. So, a tiger (Int 2) wearing a
headband of intellect +4 ends up with an intelligence of 2+4 = 2. (And a lizard (Int 1) wearing the same headband ends up with an intelligence of 1+4 = 2.)
Which kind of sucks, since you've just invested a huge amount of money in doing something cool, and it just doesn't work, but it would seem to be consistent in RAW. The alternative would be that the creature becomes a Magical Beast (augmented animal), and so not an Animal Companion, for as long as the headband is active... and likewise that casting a
fox's cunning spell on a fox would turn it into a Magical Beast for the duration of the spell. Which also works by RAW, but seems oddly convoluted somehow - and also not really what the Druid is likely to want.
(The third option, of course, is just to let the Animal Companion gain the benefits of the Int boost with no other effect - that is, it remains an Animal, and so remains an AC. But given the relative power of the Druid compared with most other classes, I'd be reluctant to give them yet more advantages.)