I'm going to have to recommend an English made shoe here. This is just my two cents -- Italian made shoes are largely overpriced, and the ones in your price range just aren't the best value. Italians make great shoes in the $1000+ price range, but in the sub-$500 you are better off with an English shoe.
Some Italians make good shoes (not just Lattanzi and Kiton). One issue is that some such as Gravati also make a lot of ugly shoes. English shoe makers generally have fewer models, and you are less likely to get something really bad.
I'd also recommend just getting one shoe for now.
Left or right?
You're a novice here (nothing wrong with that, mind you -- we've all been there) and it would be a shame to drop $1K on two pairs of shoes that you end up hating.
I agree with this. I am a novice too and notice that my tastes change very fast. AE is safe and cheap if you get them from an outlet. They are not very fashion forward but owning a pair of conservative shoes cannot hurt (funerals, meeting with in-laws, etc.). Go wild when you are sure you'll still like the shoes years from now. Otherwise, as jn3 said, you'll just be wasting your money. Mathieu