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For over a decade, Alison Loehnis was obliged to put on the same clothing day after livelong day. “I wore a uniform to school for 12 years,” said Ms. Loehnis, who is the president of influential online fashion retailers Net-a-Porter and Mr Porter. “So being able to choose what I was going to wear was something I always looked forward to.” Given these monotonous strictures, how did she develop her impeccable taste? “My mom had a great sense of style, so part of it comes from that,” she said. “Of course, I’d style my Barbie dolls too.”

Both…