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Popflex Crisscross Hourglass Flared Leggings With Pockets in Black ($65)

The flared leggings trend is picking up steam, and definitely taps into the early aughts look. You can shop this pair in five different lengths and seven different shades — though yet again, black is the most popular. The flare silhouette starts just below the knee and they have a mid-rise. The V-cut in the waistband is made to comfortably highlight an hourglass shape without pinching the skin.