22 Best Fall Outfits with Skirts You’ll Love This Season

As soon as the air gets crisp and leaves start turning golden, skirts take on a whole new personality. Unlike summer, when skirts are light and breezy, fall calls for layering, textures, and cozy combinations that make outfits both warm and stylish. The beauty of skirts in autumn is how versatile they are—you can wear them to work, a coffee date, or even for a casual walk, and they still feel season-appropriate.

From leather minis to flowy maxis, skirts open endless outfit possibilities that balance practicality with elegance. When styled with sweaters, boots, tights, and jackets, they create some of the best transitional looks for the cooler season. If you’re ready to refresh your wardrobe, here are 22 ideas to inspire your fall outfits with skirts.

Midi Skirt with Chunky Sweater

A knitted midi skirt paired with an oversized chunky sweater makes for the perfect cozy-meets-chic outfit. The balance between the fitted skirt and slouchy top creates effortless sophistication while keeping you warm during brisk mornings. Adding neutral boots or sneakers helps ground the look.

For extra polish, tuck in the front of the sweater and belt the waist. This subtle styling trick creates a flattering silhouette and adds a touch of definition without compromising comfort. A leather crossbody bag and gold hoop earrings elevate the outfit into something you could wear from brunch to a casual meeting.

Plaid Mini Skirt with Turtleneck

A plaid mini skirt instantly gives off classic fall vibes, especially when paired with a fitted turtleneck. This timeless combination works well in both casual and slightly dressier settings. Black tights and knee-high boots complete the outfit while keeping you warm.

To make the look more playful, consider layering a denim jacket or a cropped cardigan on top. A beret or structured hat adds Parisian flair, while a satchel bag ensures the outfit feels functional for everyday wear.

Leather Skirt with Oversized Blazer

A leather skirt is a bold statement piece for fall, especially when paired with an oversized blazer. The contrast between edgy leather and structured tailoring creates a balanced and modern outfit. Add ankle boots or heeled loafers to sharpen the look.

For color, try a camel or gray blazer over a black leather skirt to soften the edge without losing sophistication. A tucked-in blouse or ribbed knit underneath ensures the outfit remains put-together, perfect for work or after-hours.

Denim Skirt with Knit Cardigan

The denim skirt remains a wardrobe staple, and for fall, it pairs beautifully with a chunky knit cardigan. This look balances casual comfort with just enough structure to feel polished. Ankle boots or sneakers work well for a laid-back vibe.

Layering is key here—a simple white tee or turtleneck under the cardigan adds dimension. Throw on a scarf in earthy tones and a crossbody bag for a casual yet stylish weekend look.

Pleated Skirt with Leather Jacket

Pairing a pleated skirt with a leather jacket creates a mix of feminine and edgy. The flowy movement of pleats contrasts beautifully with the structured, rugged appeal of leather. Opt for a midi length for balance and pair with ankle boots.

Accessories can really shape this outfit—add a chunky knit scarf for warmth or switch to a silk scarf for elegance. Statement earrings or layered necklaces complete the look for day-to-night wear.

Tweed Mini Skirt with Knee-High Boots

Nothing says fall quite like tweed. A tweed mini skirt with knee-high boots creates a chic and slightly preppy outfit that’s perfect for colder days. Pair it with a fitted knit top or turtleneck for a timeless style.

To enhance the autumn vibe, layer a trench coat or wool blazer over the look. Keep accessories simple—a structured handbag and minimal jewelry allow the tweed’s texture to shine.

Wool Maxi Skirt with Fitted Top

A wool maxi skirt adds both drama and warmth, making it a fall wardrobe favorite. Pair it with a fitted knit top to balance proportions and keep the silhouette sleek. This look works particularly well with heeled boots.

A long coat or tailored jacket adds refinement, while a wide belt can define the waist. Carrying a structured handbag helps elevate the overall outfit, making it suitable for work or more formal occasions.

Corduroy Skirt with Cozy Sweater

Corduroy is a quintessential fall fabric that adds texture and warmth. A corduroy skirt with a cozy sweater is a combination that feels timeless and approachable. Pair with tights and loafers for a comfortable, everyday look.

Choose autumnal shades like burnt orange, olive green, or mustard yellow for an extra seasonal touch. A suede or leather satchel bag adds rustic charm, making this outfit perfect for coffee dates or strolls through the park.

Satin Skirt with Knit Pullover

Satin skirts don’t have to be reserved for summer or dressy occasions. Paired with a chunky knit pullover, they gain a cozy, luxe quality perfect for fall. Sneakers or ankle boots tone down the shine for daytime wear.

Adding layered necklaces and a crossbody bag gives the outfit balance between casual and chic. If you want a more elevated version, swap the knit for a fitted turtleneck and add heeled boots.

Pencil Skirt with Trench Coat

A pencil skirt in a thicker fabric like wool or tweed makes a strong fall statement when paired with a trench coat. This outfit offers both professionalism and warmth, ideal for workdays or meetings.

A tucked-in blouse or turtleneck underneath keeps the look streamlined. Pointed-toe boots or heels add length to the legs, while a structured tote ensures you’re ready for the day.

Floral Midi Skirt with Knit Top

Fall florals are moody and romantic, making a floral midi skirt a great choice. Pair it with a knit top in a neutral shade to balance the print. Ankle boots in suede or leather complete the seasonal look.

Layer with a cropped jacket to define proportions and add warmth. A wide-brim hat in a felt material enhances the autumn aesthetic while keeping the outfit playful.

Suede Skirt with Button-Down Shirt

Suede skirts bring warmth and texture that fit right into fall dressing. Paired with a crisp button-down shirt, the look balances rugged texture with sophistication. A pair of ankle boots ties the outfit together.

For layering, add a cropped sweater vest or lightweight jacket. A structured handbag or satchel complements the smart yet casual vibe.

Knit Skirt with Matching Sweater Set

Matching knit sets have become a stylish go-to for fall, offering comfort without sacrificing elegance. A knit skirt with its coordinating sweater makes getting dressed effortless. Pair with ankle boots or loafers for a polished touch.

The monochrome effect elongates your figure and creates a sleek, cozy appearance. Add a coat in a contrasting tone and finish with minimal jewelry for understated sophistication.

Wrap Skirt with Oversized Coat

Wrap skirts offer versatility and can be flattering on different body types. In fall, a wrap skirt styled with an oversized wool coat creates a cozy yet chic layered look. Heeled boots help elongate the legs and add structure.

Choose a wrap skirt in plaid or houndstooth to embrace the season’s patterns. A crossbody bag or belt bag keeps the outfit modern and practical for everyday wear.

Plaid Midi Skirt with Cropped Jacket

A plaid midi skirt paired with a cropped jacket balances playful pattern with modern proportions. Sneakers or lace-up boots keep the outfit casual yet stylish.

Layering with a turtleneck underneath enhances warmth while keeping the silhouette streamlined. Add a satchel or mini bag to keep the look youthful and functional.

Maxi Skirt with Oversized Scarf

A maxi skirt styled with an oversized blanket scarf creates cozy autumn vibes. This pairing is not only practical but also dramatic, giving a statement look while staying warm.

Neutral ankle boots or slip-on sneakers help ground the outfit. A slouchy tote bag adds functionality and casual charm.

Leather Mini Skirt with Knit Sweater

Leather mini skirts are edgy, but pairing them with a soft knit sweater balances the outfit beautifully. Black tights and heeled ankle boots create a chic, night-out-ready style.

To dress it down, swap heels for sneakers and add a casual jacket. The combination of textures makes the outfit look rich and season-appropriate.

Printed Skirt with Denim Jacket

A printed skirt, whether floral or abstract, takes on a new mood in fall when paired with a denim jacket. This look feels relaxed and approachable while still fashionable.

A scarf in earthy tones adds warmth, while boots or sneakers keep the outfit grounded. It’s a great go-to for weekend errands or casual outings.

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Pleated Maxi Skirt with Fitted Blazer

A pleated maxi skirt styled with a tailored blazer makes a powerful yet feminine statement. This pairing is polished enough for work while being stylish for evening plans.

Stick to deeper fall colors like burgundy or navy to enhance the season’s palette. Heeled boots or pumps complete the look with sophistication.

A-Line Skirt with Longline Cardigan

An A-line skirt is universally flattering, and paired with a longline cardigan, it creates a soft, flowy silhouette. This combination feels cozy and feminine, perfect for casual fall days.

Add ankle boots or loafers and a structured bag for polish. Play with textures—pair a wool skirt with a ribbed cardigan to make the look more dynamic.

Midi Slip Skirt with Oversized Sweater

A midi slip skirt adds elegance, while an oversized sweater gives comfort. Together, they create a look that’s relaxed but elevated. Sneakers or combat boots toughen it up for fall.

Adding a belt over the sweater defines the waist and gives balance to the silhouette. A crossbody bag and simple earrings finish off this effortlessly chic look.

Tiered Skirt with Knit Pullover

Tiered skirts bring movement and a playful vibe. Paired with a knit pullover, they feel whimsical yet grounded for fall. Neutral or muted shades make the look season-appropriate.

Cowboy boots or ankle boots can give the outfit extra character. A felt hat or tote bag completes the fall-ready ensemble.

FAQs about Fall Outfits with Skirts

What skirts are best for fall weather?
Wool, tweed, corduroy, denim, and leather skirts are best suited for fall as they provide warmth and structure.

Can you wear skirts in cold weather without freezing?
Yes—layering with tights, leggings, tall boots, and cozy outerwear makes skirts perfectly practical even when temperatures drop.

Are maxi skirts good for fall outfits?
Absolutely. Maxi skirts in heavier fabrics like wool or knits not only look stylish but also keep you warm while allowing layering.

What shoes work best with fall skirts?
Ankle boots, knee-high boots, loafers, and even sneakers can be paired depending on the vibe—boots are the most versatile for fall.

How do I transition my summer skirts into fall?
Pair lighter skirts with chunky sweaters, jackets, tights, and boots. Adding fall colors and layering pieces makes them season-appropriate.

Conclusion

Fall outfits with skirts aren’t just about keeping up with seasonal trends—they’re about finding the perfect balance of comfort, warmth, and personal style. With the right fabrics, layering pieces, and accessories, skirts can effortlessly transition from summer’s lightness to autumn’s cozy charm. From edgy leather minis to classic plaid skirts and flowing wool maxis, there are endless ways to style them for every occasion.

The beauty of fall outfits with skirts lies in their versatility. Whether you’re heading to work, going out for a coffee date, or dressing up for a night out, there’s a skirt look that fits the mood. Experiment with textures, play with proportions, and make each outfit your own. With these styling ideas, you’ll step into fall feeling confident, chic, and ready for the season.