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Slice the top and bottom of both oranges with a paring knife.
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Set one of the flat sides on your work surface. From top to bottom, following the curve of the fruit, cut away peel and white pith.
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Trim off any remaining pith. Holding the orange over a bowl, cut along both sides of each segment, staying close to the membrane, to release. Repeat process with remaining orange; set segments aside.
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In a large bowl whisk together vinegar and sugar until well combined.
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Slowly whisk in vegetable oil and season with salt and pepper.
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Add cabbage, pepper, orange segments, and cilantro
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Toss to coat.
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Keep slaw refrigerated until ready to use, up to 2 hours.