In a small bowl, combine the olive oil, red wine vinegar, oregano, salt, and pepper. Whisk everything together until it looks slightly thickened and well blended. This little dressing is what ties the whole salad together, so take a moment to taste and adjust it.
Slice your tomatoes into wedges, or halve them if you are using smaller varieties like cherry tomatoes. Thinly slice the sweet onion so it distributes evenly throughout the salad. Place both into a medium mixing bowl.
Pour the dressing over the tomatoes and onion. Gently toss so every piece gets coated without breaking apart the tomato wedges. Taste it once more and add extra salt or pepper if needed.
This salad tastes best when served immediately at room temperature. Tomatoes lose their texture in the fridge, so it is worth enjoying this one fresh rather than saving it for later.