Every season is Princess Diana season because even close to three decades after the royal's tragic passing, her style remains both timeless and aspirational—all while being eminently achievable for us common folk. Among other things, Diana showed us how to style capri pants in the spring and jeans tucked into boots in the fall.
Speaking of knee-high boots, the late Princess of Wales loved a boot-and-midi-skirt moment—a styling trick which the current Princess of Wales, aka Kate Middleton, clearly learned from her. There's an iconic photo of Diana bringing baby Prince Harry(!) to school while wearing the uniform: bunchy brown leather riding boots under a glorious chocolate suede ankle-length belted skirt. The crowning jewel of it all, if you will, was the white turtleneck balloon-sleeve sweater she tucked into it, casually, as if she hadn't given it a second thought. As ever, the outfit was perfect and thought-through without being try-hard. Also, somehow, it's totally current for 2026—even though the picture was taken in 1988. Go figure.
Re-Create Princess Diana's Outfit
