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Pastel Pleated Tennis Skirt With Nike Socks. Gray sweater, plaid skirt, red hat, bag, and ankle boots. Box Pleat Gingham Skort, 19.99, Zara - buy now. The tops that could be worn with this look are basically limitless. Dis symmetry and slit skirt will be the trendiest in long skirts 2023 fashion. SALE Bolle Women's 13 Inch Tennis Skirt Black $48 20% OFF $38.40. Check out our black tennis skirt selection for the very best in unique or custom, handmade pieces from our women's clothing shops. Wear it with an oversized sweatshirt, sweater vest, or our You're the One Top for a trendy look. 913. Another benefit to wearing high socks with your tennis skirt outfit (aside from looking like Britney Spears circa 1998) -- increased mobility. The full outfit fits great with black stockings, a black handbag, and ankle boots. White Sweatshirt with Tennis Skirt. 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