Rinse the pearl barley under cold water to remove any debris. In a medium saucepan, combine the rinsed barley and water or vegetable broth. Bring to a boil over medium-high heat.
Once boiling, reduce the heat to low, cover, and let it simmer for about 30-35 minutes, or until the barley is tender but still chewy. If the barley absorbs all the liquid, add a little more broth or water as needed.
After cooking, drain any excess liquid and allow the barley to cool for about 10 minutes in a large mixing bowl.
While the barley is cooling, prepare the vegetables. Halve the cherry tomatoes, slice the Kalamata olives, and chop the fresh parsley.
In a small bowl, whisk together the extra-virgin olive oil, dried oregano, salt, and black pepper to create the dressing.
Once the barley has cooled, add the cherry tomatoes, olives, feta cheese, parsley, and dressing to the bowl. Gently toss all the ingredients together until well combined.
Taste the salad and adjust seasoning if necessary. For an extra flavor kick, let the salad sit for about 15 minutes before serving to allow the flavors to meld.