While I understand why some people don’t like to compare the current Princess of Wales to the late Princess Diana, I find it fascinating to examine how royal style has evolved (or stayed the same) over the years. My discussions are purely sartorial in nature and are never meant to pit the two women against each other. It’s not a competition! On the contrary, I enjoy celebrating how each has left a mark on royal fashion in her own way. Both women have consistently proven that royals can set trends while working within the confines of their roles.

One of the clearest examples of this evolution across generations of royals is Kate Middleton‘s newest outfit. Echoing a classic Princess Diana formula, Princess Kate wore an A-line midi skirt with knee-high boots and a blazer. The only difference? Kate modernized Diana’s look by opting for a cropped jacket instead of a full-length one. This small tweak creates a fresher, more contemporary silhouette while still nodding to Diana’s classic approach. Scroll down to see how the looks compare.

Kate Middleton’s Skirt-and-Boots Outfit, September 2025

Kate Middleton wears a midi skirt with knee-high boots

(Image credit: Getty Images)

On Kate Middleton: Me + Em Suede Cropped Military Jacket ($475); Ralph Lauren Collection Brown Birdseye Tweed Evilyn Skirt ($2100); Polo Ralph Lauren belt; Gianvito Rossi boots; Spells of Love earrings; Sudbury Silk Mills Shop scarf

Princess Diana’s Skirt-and-Boots Outfit, January 1991

Princess Diana wears a midi skirt and knee-high boots

(Image credit: Getty Images)

Re-Create Kate Middleton’s Newest Outfit