Actually, I'm looking more for confirmation of what I think might be correct. I've just read through a bunch of posts on this topic on here but some of the answers were a little confusing/conflicting, so I'm just trying to get clarification.

We will be in Spain September 19 - October 6 of this year, and we will be traveling via car through a total of 4 regions. (Madrid, Extremadura, Andalucia, La Mancha) I'm trying to think ahead to what I might need to pack clothing-wise to see if I need to buy new stuff. I have checked the temperature tables and such, but they normally cover a whole month and if Spain is anything like Southern California, those temps can vary! So...

I'm thinking the weather will mainly be warm to hot. Would that be a good guess? I'm also thinking the evenings might have a chance of getting cool? I also read on here that there is a greater chance of rain in the beginning of Oct. Is that true? I'm planning a wardrobe that is geared toward warmer weather, but with a long-sleeved shirt, a light jacket (that does double duty as a rain coat), and a nicer sweater for evening thrown in. And, as always, I will be taking my umbrella with me! Is this a pretty safe bet? I don't like to buy clothes on vacation in other countries because sizing can be such a problem.

Also, I will be traveling with my boyfriend who typically lives in jeans and jean shorts. I know the jeans will be heavier, but it's his suitcase! Any tips I can pass along to a guy? Specifically looking for evenings, if we should decide on a nicer restaurant. He doesn't own a sport coat or even a tie! Can he get by with a nice pair of slacks and a dress shirt?

(Yes, I'm know...I am a self-admitted sufferer of Obsessive/Compulsive Disorder, but any advice/suggestions/comments are sincerely appreciated!)