At brunch with some other bloggers yesterday, I mentioned that I have just a few rules about pairing wine and food. Upon hearing me rattle them off, Elise suggested I post them. But looking at my old SFist post on the topic, I realize that my rules haven't changed. Read that first, especially the part where I say to not sweat it.
Some other bloggers at the table brought up points that I don't cover in the post. Clotilde asked about regional pairings, and this is a guideline I tend to follow, but I find it a rough rule. For one thing, only Europe and maybe South Africa have a long enough history of native cuisine and wines to pair. But even in Europe, wine making styles have changed over time. The traditional wine of Sancerre, after all, is a red, not the more common white of today. Bordeaux used to use Rhône grapes in varying amounts. Are you talking about a classic Barolo or one made in the modern, international style? A Chianti or a Super Tuscan? And is the chef keeping close to the traditional form of the dish, or using it as a springboard for a new concept? Regional pairings can be surprising: I consider Port and Stilton a regional pairing because the British controlled Portugal of the 600-year-old alliance and old trade agreements between Britain and Portugal, and the fact that the British control its most famous wine houses.
Amy added that you can make a choice to contrast the flavors in the wine with the food or make them comparable. I do this without thinking, based on my mood, so I tend to forget about it as a rule.