After 26 years at J. Crew — and nearly a decade at the helm of the brand — designer Jenna Lyons is stepping down as its creative director, as CEO Mickey Drexler revealed on Monday. Over the course of her tenure, Lyons became in many ways the aspirational figurehead of the very woman she designed for, broaching the divide between designer and street style star. (A tricky gap to cross, as Justin O’Shea recently learned.) She rolled up to the Met Gala flanked by Jenni Konner and Lena Dunham of Girls, each wearing a tuxedo; she appeared front-row at countless shows, from Altuzarra to Prabal Gurung, while also hosting her own presentations for J. Crew — often featuring non-model models. Her look, a little androgynous, often tended towards power suiting and polished trousers, topped off with her trademark dark-rimmed glasses and neat updo. On the occasion of Lyons’s departure from J. Crew, we look back on a few of her best street style moments at fashion week and beyond through the years.