There was a time when dressing for middle school meant begging your parents for the cutest outfits: perhaps a Hollister graphic tee or the latest Air Jordans. These days, the look is somewhat more casual. At 7:50 a.m. in New York City, you’ll find hoards of tweens rushing to school in matching pajama pants. Eleanor Woodsworth, 11, of Brooklyn, says that the trend started several months ago. She and her friends would collectively pick a pattern from the retailer Five Below, which...

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