thesaurus wrote:I think that his philosophical/rhetorical writings are easier than his orations. When I was still fairly new to reading unadapted Latin, I worked on his "De Amicitia" and "De Senectute"--the two are often paired up. Not terribly long, not terribly complicated. Plus, you can comprehend most of what he's saying without needing outside historical context, unlike most of his speeches. If you look around, you should be able to find editions with lots of notes for people in your position. I'm rereading these works now, and I find them quite enjoyable.
The first oration against Catiline, "In Catilinam," is a common introduction to Latin prose, but I don't think it's necessarily easy. However, it may be a good pick if you prefer the excitement of his speeches.
Cicero uses a fairly small vocabulary, so the more of him you read, the easier his other works will become. This is true for any author, but I have found that Cicero has a pretty consistent style and register, and he tends to stick to fairly common vocabulary. You won't find many rare or strange words in his writings. The language/style of his philosophical writings does differ from his orations (which in turn differ depending on their audiences), but it's nothing drastic.