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Toss coleslaw mix, pineapple and 1 tablespoon oil together in a medium bowl until evenly coated. Set aside at room temperature.
In another medium bowl, toss shrimp with chile-lime seasoning until evenly coated.
Heat the remaining 1 tablespoon oil in a large cast-iron skillet over medium-high heat until shimmering. Add the shrimp; cook, undisturbed, until mostly cooked through and golden brown on the bottoms, 2 to 3 minutes. Flip the shrimp; cook, stirring often, until opaque and fully cooked through, 30 seconds to 1 minute.
Divide the shrimp among 8 tortillas; top each with coleslaw mixture. Serve with lime wedges, if desired.