Tuscan kale (also called dinosaur or lacinato kale) has a slightly sweeter flavor than regular kale. Choose the smaller leaves, which are tender and more mild than larger leaves.
Heat 2 tablespoons oil in a large skillet over high heat. Add kale and 2 tablespoons water. Reduce heat to medium. Cook, covered, stirring occasionally, until wilted, about 4 minutes. Season with salt. Cook, uncovered, stirring occasionally, until kale is tender, about 15 minutes more.
Clear a space in center of skillet, and add remaining tablespoon oil, the garlic, and chile. Cook until fragrant, about 1 minute. Stir to combine. Season with salt and pepper.