In/out of pocket Definition 1 of 3Pro Tip 1/3Negative Outcome Used when someone has lost money, often unexpectedly or unfairly. He sold his car at a loss and was out of pocket. Pro Tip 2/3Financial Disappointment Expresses a sense of regret or dissatisfaction related to financial loss. After the concert cancellation, many fans were left out of pocket. Pro Tip 3/3Unexpected Costs Highlights unplanned expenses leading to monetary loss. The storm damage led to high maintenance costs, leaving us out of pocket.