1. Look for a "Harvest Date" or "Crop Date" on the bottle. The "Harvest Date" tells you exactly when the olives were picked. Olive oil is best if it's used within 18 to 24 months of harvesting. If more time has passed, the oil is still edible, but is probably better for cooking than drizzling over salads. Many olive oil brands have a "best if used by" date, but this doesn't tell you how long the olives were sitting before being pressed. Plus, various companies may have different views on how long olive oil is still good.
2. Expensive olive oil isn't necessarily worth the splurge. Most of the time, the extra money you pay doesn't even make it back to the grower. Excellent olive oil comes from all over the world including places like California, Spain, Italy, and Greece and increasingly Australia and South America. The soil and other environmental factors influence the growth, but taste quality is also heavily dependent upon the care the farmer takes growing, picking, and pressing the olives.
3. Look for certifying seals. If you're dead set on buying olive oil from a specific region, look for certifying seals that authenticate the olive oil is grown and pressed in one location. Certifying seals also help prevent olive oil fraud, including lying about an olive oil's origin or the ingredients in the product. The Toscano seal certifies that the olives are grown, pressed, and packaged in Toscano, Italy. DOP and IGP are other seals that guarantee the production and processing of the olive oil was done in a specific geographical area.