The Skirt-And-Boot Combo That Looks Great Together For Fall 2026

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The transition from summery sunshine to autumnal chills typically necessitates a major wardrobe shift. Fortunately, there's a celebrity-approved skirt-and-boot combo that will easily translate summer-ready bottoms into the new season: the midi skirt with tall boots. 

The most comfortable skirt and dress trends of summer 2026 included the '90s-inspired midi skirt that appeared on runways and in street style. The silhouette was worn by notable stars of the decade, like Sarah Michelle Gellar and Britney Spears. Though this silhouette is worn in many fabrics today, the slip-inspired iterations trimmed in lace remain a fashionable choice that is majorly nostalgic.

Skirts that fall at the knee or mid-calf continue to be a stylish option, with a pair of tall boots being the perfect way to transition the pieces into fall. For 2026, vogue iterations of the footwear include leather mid-calf boots, fun cowboy boots, and kitten heels. When it comes to styling, fashionable celebs have demonstrated several ways to wear this trend.

Tall boots and a midi skirt are a celebrity-approved combination for the cold-weather seasons. For example, Emily Ratajkowski was dressed for the weather when spotted in New York City in January 2024, combining an animal-print skirt trimmed with lace and kitten-heel leather boots. She stayed warm with a roomy leather jacket and simple black scarf. Overall, the pairing of the jaguar skirt and leather boots creates a chic, sexy vibe, with Cicy Bell's Silk Satin Leopard Midi Skirt being a comparable option.

Style icon Katie Holmes leaned into '90s minimalism with her midi skirt, showcasing another method for styling the pieces. When spotted in NYC in February 2025, the actor donned pointed-toe boots in an inky black shade with a silver skirt. She added a simple white top and blue blazer, completing the outfit with a chunky clutch. Because each element of this ensemble is relatively simple, they come together to create a look that feels very classic. For a similar shoe style, Steve Madden's Rizk Boots make a great starting point.

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Lastly, Zaya Wade opted for a preppy take on the combination when pictured in September 2025. The model, who's the daughter of Dwayne Wade, wore a navy, pleated skirt with brown moto boots. A pinstripe button-up with a white collar really brought the preppy energy, while a tawny handbag and wire-frame glasses finished out the look. To similarly channel academia with a skirt-and-boot outfit this fall, check out the Solid Box Pleat Skirt Top of Knee from Lands' End.