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The dress-and-jean combo helped me look like I wasnt trying too hard, which is actually why I think the look was popular with female celebrities at the time. Besides balancing between dressy and casual, the juxtaposition of super feminine dresses with denim pants also offered a cheeky way of playing with gender norms, Idacavage said, adding that the trend coincided nicely with the third-wave feminist movement and allowed women to channel a little rebellious spirit

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Complete the look with a pair of black tights and ankle boots