Sauté okra in 1 Tbsp. hot oil in a large cast-iron skillet over medium-high heat 4 to 5 minutes or until browned. Transfer to a bowl.
Cook tomatoes in 1 Tbsp. hot oil in skillet over medium-high heat, stirring occasionally, 2 to 3 minutes or until skins are charred. Place in bowl with okra.
Sauté shrimp, garlic, and dried crushed red pepper in remaining 1 Tbsp. hot oil in skillet over medium-high heat 2 to 3 minutes or just until shrimp turn pink. Stir in okra and tomatoes. Add salt and pepper to taste; cook 1 to 2 minutes or until thoroughly heated. Garnish, if desired.