Advances in computer vision and machine learning are changing the way people dress, and buy clothes. Given the vast space of fashion problems, where can data-driven technologies provide the most value? To understand consumer pain points and opportunities for technological interventions, this paper presents the results from two independent need-finding studies that explore the gold-standard of personalized shopping: interacting with a personal stylist. Through interviews with five personal stylists, we study the range of problems they address and their in-person processes for working with clients. In a separate study, we investigate how styling experiences map to online settings by building and releasing a chatbot that connects users to one-on-one sessions with a stylist, acquiring more than 70 organic users in three weeks. These conversations reveal that in-person and online styling sessions share similar goals, but online sessions often involve smaller problems that can be resolved more quickly. Based on these explorations, we propose future personalized, online interactions that address consumer trust and uncertainty, and discuss opportunities for automation.