Like we said in the title, we're not talking about skinny jeans or leggings today. This fall, the chicest people are styling their boots with something infinitely cooler: skirts. Whether it's a structured midi, a fitted pencil, or a pleated mini, the balance of leather boots with a skirt feels directional in 2025—equal parts polished and confident. It's the kind of outfit that doesn't try too hard but immediately reads as perfectly stylish.
Designers leaned heavily into the boots-with-skirts formula this season, pairing knee-high boots with tailored wool miniskirts and tall riding boots with sleek, mid-length silhouettes. It's a look that hints at old-school prep but has a modern twist. Think tonal knits, longline coats, and a hint of bare leg—just enough to make the boots the main event. It's effortless but intentional.
The key is in the contrast. Chunky Western boots instantly toughen up a soft pleated skirt, and pointed-toe leather boots make even a basic denim midi feel like a runway moment. It's not about matching. It's about creating tension. The proportions feel new again, especially when balanced with a sharp blazer or slouchy turtleneck.
If you're still reaching for jeans, consider this your sign to switch it up. The boots-and-skirt combo is the understated power move of the season that's smart, sophisticated, and quietly sexy. Every editor, model off duty, and fashion insider has already caught on. It's the fall outfit formula that feels both classic and completely of-the-moment.
Below, see how to style fall boots with skirts this season and shop the essentials along the way.
Get the look: Black turtleneck + Midi skirt + Tall leather boots
Get the look: Oversize jacket + White skirt + Tall leather boots
Get the look: Leather jacket + Black skirt + Leather boots
Get the look: Cropped sweater + Midi skirt + Moto boots
Get the look: T-shirt + Cardigan + Black skirt + Printed tall boots
Get the look: Sheer top + Polka-dot skirt + Suede tall boots
Get the look: Cropped jacket + Embellished skirt + Fitted tall boots
Get the look: Fringe cape + Miniskirt + Western boots
Get the look: Boxy jacket + Miniskirt + Mid-calf boots
Get the look: Matching set + Tall fitted boots + Clutch
Get the look: Black turtleneck + Suede long skirt + Pointed-toe boots
Get the look: Cardigan + Long leather skirt + Leather boots
Get the look: Turtleneck sweater + Fringe skirt + Fitted leather boots
Get the look: Jacket-and-skirt set + Leather belt + Tall leather boots
Get the look: Long leather coat + T-shirt + Cardigan + Tall suede boots
