Long Skirt Outfits for Fall with Boots: 10 Perfect Looks to Stay Cozy & Chic
As a fashion writer, one of my favorite things about fall is the beautiful layering opportunities—chunky knits, rich textures, and, of course, boots! But if there’s one combo that consistently steals my heart (and dominates my Pinterest boards), it’s long skirt outfits for fall with boots. They’re feminine, cozy, and effortlessly stylish. And after spending hours curating this post, I can confidently say these 10 looks will inspire you to refresh your wardrobe.
Whether you're headed to work, brunch with friends, or just love dressing for the crisp fall air, there’s a skirt + boot pairing here for you. Let’s dive into some seriously chic inspo.
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1. The Classic Jean Jacket + Midi Skirt Combo
This is a fail-proof fall outfit. A soft, flowy midi skirt paired with a structured jean jacket creates a perfect balance of laid-back and polished. Add a pair of ankle boots—flat or heeled—and you've got a transitional look that works for nearly any daytime activity.
Personally, this is my go-to for early fall coffee dates. I love mixing prints on the skirt with a neutral top underneath the jacket.
Style Tip: Opt for boots in camel or taupe to make prints pop.
2. Work-Ready: Modest Midi Skirt, Tights & Sleek Boots
Dressing for the office during the fall season can feel like a challenge. You want warmth, modesty, and style all in one. Enter: the modest midi skirt with opaque tights and heeled ankle boots. Tuck in a blouse or thin turtleneck and throw on a structured blazer to complete the look.
This is a great way to bring feminine energy into a professional setting while still keeping warm and stylish.
Style Tip: A pencil or A-line silhouette adds just enough shape without being restrictive.
3. Denim Maxi Skirt + Chunky Knit + Knee-High Boots
When I think of casual fall style, this look immediately comes to mind. A denim maxi skirt brings texture and structure, while a chunky knit adds that cozy vibe. Pair with knee-high boots and you're golden.
This outfit is one I recently wore apple picking, and let me tell you—it got compliments all day!
Style Tip: Choose boots that sit right under the hem of your skirt to create a seamless silhouette.
Product Recommendation #1: Chunky Cable Knit Sweater
ANRABESS Women’s Casual Long Sleeve Cable Knit Sweater
This Amazon best-seller is soft, slightly oversized, and perfect for tucking into skirts or layering over dresses. Available in a wide range of fall hues like rust, ivory, and sage, it’s a must-have layering piece.
Why I love it: It’s thick enough to keep warm but lightweight enough to wear indoors without overheating.
Snag this cozy-chic sweater and complete your fall look! Shop here on Amazon
4. Leather Long Skirt + Statement Boots
Now, if you’re ready to turn heads, a leather skirt (faux or real) is your ticket. Pair it with a sleek top and statement boots—think snakeskin print or metallic detailing—for a daring, editorial look.
I wore a version of this to a local art gallery event, and it felt effortlessly stylish with just the right touch of boldness.
Style Tip: Keep your top neutral and minimal to let the skirt and boots shine.
5. White Skirt + Fall Sweater + Suede Boots
Yes, you can wear white after Labor Day—and you should. A white skirt with a camel or tan sweater, paired with suede boots, creates an ultra-luxurious fall look. It’s crisp, clean, and a little unexpected.
White skirts add freshness to the deeper tones we usually see in fall wardrobes, and they photograph beautifully for social media.
6. Plaid Skirt + Oversized Cardigan + Combat Boots
This outfit brings cozy vibes with a side of attitude. Think a high-waisted plaid skirt, chunky cardigan, tights, and lace-up combat boots. It’s perfect for running errands, sipping cider, or weekend road trips.
I love mixing classic plaid with modern elements like a cropped cardigan or crossbody bag. It’s also a subtle nod to grunge while still staying polished.
Product Recommendation #2: High-Waisted Plaid Midi Skirt
IDEALSANXUN Women’s Plaid A-Line Midi Skirt
This skirt is structured yet flowy, with a flattering waistband and just the right amount of swish. The plaid comes in classic autumn tones—think burgundy, navy, and forest green.
Why I love it: It’s super versatile for both work and casual wear and looks gorgeous with a tucked-in sweater or blouse.
Fall in love with plaid all over again—grab this skirt on Amazon
7. All-Neutral Maxi Skirt Ensemble with Suede Booties
There’s something so calming about an all-neutral outfit in fall. Try a cream or taupe maxi skirt, paired with a light beige sweater and soft suede booties. Layer delicate gold jewelry and carry a leather crossbody to polish off the look.
This is one of those outfits that looks expensive—even if it’s not. Minimal effort, major style.
8. Tights + Pleated Skirt + Slouchy Boots
Pleated skirts are inherently elegant, but when styled with black tights and slouchy boots, they gain a laid-back coolness perfect for work or play. You can easily dress this up with a blazer or down with a denim jacket.
Product Recommendation #3: Opaque Thermal Tights
No Nonsense Women's Super Opaque Control Top Tights
Don’t underestimate the power of a great pair of tights. These thermal tights are thick, comfortable, and stay put all day. Plus, they come in classic shades that go with every skirt in your closet.
Why I love them: They’re warm without being bulky, and they add just enough coverage for chillier mornings.
Stay warm and stylish—grab your pair on Amazon
9. Denim Midi Skirt + Longline Coat + Booties
A denim midi skirt is a fall MVP. Pair it with a thin turtleneck and a longline coat, then finish with pointed booties. It’s a city-chic look that’s perfect for museum days, shopping trips, or casual office environments.
Bonus: It’s super easy to style around. Swap your top or boots, and you’ve got a whole new outfit.
10. Leather Midi + Plaid Blazer + Block-Heel Boots
If you’re going for a boss-girl vibe, this is the ultimate fall power outfit. A leather midi skirt, plaid blazer, and block-heel boots scream confidence and style. It’s perfect for presentations, networking events, or just feeling like your most powerful self.
This is one of my favorite "boardroom to bar" looks—it looks like effort, but it's all about smart layering.
- Boot Height Matters: Choose ankle boots for midi skirts, and knee-highs for maxis to balance proportions.
- Layer Smartly: Add interest with belts, scarves, and textured fabrics like wool or ribbed knits.
- Mix & Match: Most of these skirts can be styled multiple ways with different boots—maximize your wardrobe!
Final Thoughts
There you have it—10 incredibly stylish long skirt outfits for fall with boots to keep you cozy, chic, and confident this season. From casual days in denim to power plays in plaid and leather, the possibilities are endless.
Writing this blog post truly reminded me of why I love fashion—it’s a personal, creative way to embrace every season with confidence. I hope these looks sparked ideas for your own fall wardrobe!