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Tomatoes in Chile-Fennel Oil

['1/2 cup olive oil', '2 tablespoons crushed red pepper flakes', '1 tablespoon fennel seeds', '3 pounds large tomatoes, preferably heirloom, sliced into 1/4"-thick rounds', '1 tablespoon (or more) red wine vinegar', 'Flaky sea salt']

Cook oil, red pepper flakes, and fennel seeds in a small saucepan over medium-low heat, stirring occasionally, until oil around spices is sizzling, about 5 minutes. Reduce heat to low and continue to cook until oil is infused with flavor and rusty-orange in color, 20–30 minutes. Let cool.
Arrange tomatoes on a large platter and drizzle with vinegar, then chile-fennel oil. Season with more vinegar if desired and sprinkle with salt.

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