Sixteen years ago, Marc Jacobs was appointed creative director of luxury powerhouse Louis Vuitton with the goal to update the line’s conservative looks. “I was given an incredible amount of freedom,” he previously told InStyle. “A luxury brand must be based on quality, but it’s equally about pieces that delight. Luxury is a whim that tugs at your heart.” And he succeeded, reviving the 159-year-old brand with rich, desirable (and at times, fearless) pieces without completely losing touch with the brand’s heritage. With each collection, Jacobs has blazed the trail, setting the tone for every season. And while the spring/summer 2014 show served as his swan song (which referenced previous shows with one set), we also took a look back at his remarkable tenure at Louis Vuitton. See our five favorite looks from standout collections above, and click through for five unforgettable moments, from covetable collaborations to stellar runway backdrops.