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LATE SOCIALITE NAN KEMPNER once told Lauren Santo Domingo she preferred the company of young people because they kept her current. “That stuck with me,” said Ms. Santo Domingo, 41. “I always want to be curious about what’s new. I say to myself, ‘Why be boring?’ It’s my mantra.”

It could also be the unofficial guiding principle of Moda Operandi, which Ms. Santo Domingo co-founded in 2011 as an online trunk show that let shoppers preorder directly from the runway days after a fashion show instead of waiting months to see…