Place bacon in a large skillet and cook over medium-high heat, turning occasionally, until evenly browned, about 10 minutes. Drain the bacon slices on paper towels.
Cook and stir okra in the same skillet used for bacon until tender and browned, 10 to 15 minutes. Remove and drain on paper towels.
Combine bacon, okra, tomato, green onion, and green bell pepper in a bowl.
Whisk oil, sugar, and vinegar together in a microwave-safe bowl. Heat in microwave on high for 1 minute, stirring every 10 seconds, until dressing is boiling and sugar is dissolved. Pour over vegetables right before serving; toss to coat.