7 Cool Skirt & Boot Pairings To File Away For Your Fall Outfits Needs

Your pants will be jealous.

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A fashion week guest seen wearing a fringed skirt with cowboy boots and a leather jacket

Fall is a season that makes it exceptionally easy to get enthusiastic about dressing up. The temperatures dip low enough to green-light wardrobe staples like wool blazers and leather boots, and a fresh palette of burnt color tones and cozy patterns come into focus. And even if you’re feeling a bit blue about saying farewell to carefree summer style, let the excitement of autumn fashion perk you up. One such combination that always hits the mark is a stylish skirt and boot outfit.

It’s the kind of duo that’s always reinventing itself. You can play around with textures, colors, volume, hemline, heel height, and about a hundred other variations that make each skirt and boot coupling feel utterly unique. On the runways, you see this diversity across the board, like at Chloé where then Creative Director Gabriela Hearst showed a leather midi skirt with cowboy boots for a sleek take on Western dressing. Or at Jil Sander, where an olive green boucle miniskirt suit was accessorized with glossy pointed-toe booties for an edgy take on 9-to-5 style.

Chloe Fall/Winter 2023
Jil Sander Fall/Winter 2023

For Shop Le Point founder Pauline Montupet, her new fall arrivals invite this kind of mixing and matching between skirts and boots. “I love a stretch leather boot paired with a trouser style midi skirt,” she says. “The stretch leather fits nice and snug around the ankle giving it a really sleek, polished look that also has a little touch of S&M since they give off a latex stocking vibe.”

For stylist Neelo Noory, proportions matter most. “If I’m wearing a lower boot, I’ll pair them with a slim knit midi skirt that comes below the knee, but that doesn’t cover the boot,” she says. “With tall boots, I’d do a past-the-knee skirt so that it covers the top of the shoe.” Noory also has a few color combinations in mind for the coming season. “Warm fall tones with something like a baby blue boot would look really nice,” she notes.

Ahead, kick off the new season with seven skirt and boot pairings ahead — plus all the outfit ingredients you might need to flesh out your look.

Update Uniform Staples

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A khaki skirt will forever feel like a nod to collegiate school uniforms. Lean into the nostalgia and modernize the look by pairing yours with sock boots. Up top, a leather blazer and cropped button-down shirt solidifies the back-to-school aesthetic, with a rebellious twist. If you’re not feeling the bare midriff situation, a crisp poplin shirt makes for an equally stylish substitute.

Rethink The Cowboy Boot

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If you’re used to pairing your cowboy boots with prairie dresses and cottagecore tops, try a new direction by pairing yours with a mini skirt and long coat. Underneath, minimalist layers like a crisp button-down shirt and of-the-moment waistcoat will tie the look together. And for a touch of funk, accessorize with sunglasses in a slim, rectangular silhouette.

Play Up Print And Color

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It’s not uncommon to slip into a color drought once cold weather arrives, but resist the temptation and try brighter hues for your next skirt and boot combo. Here, the lug sole white boots help to ground the vibrancy of the striped sweater and psychedelic print mini, as does the texture of silver chainlink jewelry.

Double Down On Denim

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A denim-on-denim look is a perennial pairing to keep in your back pocket for days when there’s not enough time to coordinate an outfit. For fall, try a jean jacket and midi skirt with a pair of booties in a shade of cream. Leave the last few buttons of the jacket undone to give the silhouette a perfectly undone look.

Go High On The Thigh

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A blazer and plaid pencil skirt pairing can feel a tad traditional, but with the addition of these over-the-knee slim boots, the look is — instantly — rendered chic and interesting. Test drive this in your own wardrobe by styling together staples (a wool jacket, check-print skirt, cashmere sweater) and add in this style of boot, it works every time. The bright red bag doesn’t hurt, either.

Channel Nostalgia

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If your personal style skews more playful and experimental, try this look that feels like a subtle nod to Almost Famous’ Penny Lane. The shag coat sits front and center, while the denim skirt and tall, chunky boots play stylish supporting roles. Underneath, a simple camisole brings the outfit together without distracting while a shearling bag adds to the cozy texture.

Reinvent The Mini

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Once it’s deep, frigid winter, mini skirts will be — regrettably — off the table, so embrace autumn temperatures and pair yours with a long coat and tall boots for a look that feels plucked from the streets of Paris (like this one). The floral embroidery on the sweater plays off the skirt’s wavy print, and the simple gold hoops give the perfect finishing polish.