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What To Wear With Flare Jeans 2024. Your flared jeans are fun, playful, and the perfect balance of casual. See on abercrombie & fitch. From baggy jeans to the polarizing skinny jeans silhouette, shop these styles now. Ultimately, the best shoes to wear with your flared jeans depends on the aesthetic you’re aiming for and whether you want to dress the look up or down.