Julie Bornstein, the former fashion and beauty executive turned serial entrepreneur, has spent years trying to build a fashion shopping search engine. In 2018, the e-commerce veteran, who previously helped scale businesses at Stitch Fix and Sephora, raised $30 million in Series A financing from NEA and others to jumpstart the personalized shopping app The Yes. (The company modestly exited in a cash-and-stock deal with Pinterest in 2022.) Two years later, she raised another $50 million from Google and V.C.s like Forerunner and Index to launch Daydream, which bills itself as fashion’s answer to ChatGPT. Bornstein was trying to christen digital retail’s A.I. era, and at the perfect time.