
Hello my stylish friends, Emily here! As the autumn leaves begin their magnificent color transformation, there’s no better time to embrace one of the most versatile and flattering pieces in a curvy woman’s wardrobe: the skirt.
Often overlooked in favor of pants, skirts offer incredible opportunities to celebrate your curves while staying comfortable and chic throughout the changing seasons.

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Autumn is the perfect season for skirt outfits the weather allows for creative layering, the rich fabrics feel luxurious against your skin, and the styles naturally complement curvy figures.
Whether you prefer flowing maxis or structured minis, there’s a perfect autumn skirt outfit waiting to make you feel absolutely fabulous.
I’ve curated 12 plus size autumn skirt outfits that showcase different styles, lengths, and ways to layer for the season. Get ready to fall in love with skirts all over again!
Why Skirts Are a Curvy Woman’s Autumn Secret Weapon
Skirts offer unique advantages that make them particularly wonderful for plus-size autumn styling:
- Natural Shape Enhancement: A-line and fit-and-flare skirts naturally highlight your waist while skimming over hips and thighs beautifully.
- Layering Potential: Skirts provide the perfect foundation for autumn layering with tights, boots, and various tops.
- Comfort and Ease: Unlike pants that can constrict, well-chosen skirts allow for comfortable movement throughout your day.
- Versatility: The same skirt can create multiple different outfits with simple top and accessory changes.
- Seasonal Fabric Options: Autumn skirts come in wonderful textures like corduroy, wool, velvet, and thicker knits that feel luxurious and drape beautifully.
Your Autumn Skirt Style Guide: 12 Flattering Outfits
I’ve designed these outfits to work with various skirt styles and for different autumn occasions, from casual weekends to office days.

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I. Everyday Casual Comfort
These looks are perfect for weekend adventures, coffee dates, and casual autumn days.
1. The Midi Skirt and Sweater Set

A flowing midi skirt in an autumn floral pattern paired with a fitted turtleneck sweater creates the perfect balance of comfort and style. The fitted top defines your waist while the skirt provides ease of movement. Add ankle boots and a crossbody bag for complete casual chic.
2. The Denim Skirt and Boots Combination

A high-waisted denim skirt (choose one with some stretch) layered over opaque tights and paired with knee-high boots and a chunky sweater is autumn perfection. The denim provides structure while the tights and boots keep you warm and stylish.
3. The Corduroy A-Line Skirt

A corduroy A-line skirt in autumn colors like mustard or burgundy paired with a simple long-sleeve tee and sneakers creates an easy, comfortable outfit. The A-line shape is universally flattering, and corduroy is perfectly seasonal.
II. Office Appropriate Elegance
These skirt outfits transition beautifully from work to after-work activities while maintaining professionalism.
4. The Pencil Skirt and Blazer Ensemble

A stretch ponte pencil skirt in a dark neutral paired with a silky blouse and structured blazer creates powerful office style. The pencil skirt highlights your curves professionally while the stretch fabric ensures comfort during long workdays.
5. The Pleated Midi and Turtleneck

A pleated midi skirt in wool or heavy crepe paired with a fitted turtleneck strikes the perfect balance between professional and fashionable. The pleats add movement and interest while maintaining office appropriateness.
6. The Wrap Skirt and Button-Down

A faux leather wrap skirt paired with a crisp button-down shirt creates an interesting texture contrast that’s both office-appropriate and fashion-forward. The wrap style allows for adjustable fit throughout the day.
III. Special Occasion Style
These outfits are perfect for autumn weddings, parties, or date nights when you want to feel extra special.
7. The Velvet Maxi Skirt

A velvet maxi skirt in jewel tones like emerald or burgundy paired with a delicate silk blouse creates breathtaking autumn elegance. The rich fabric feels luxurious, and the maxi length adds drama and sophistication.
8. The Tiered Ruffle Skirt

A tiered ruffle skirt in dark florals or solid colors creates beautiful movement and romance. Pair with a simple fitted top to balance the volume and let the skirt be the star of your outfit.
9. The Sequined Midi Skirt

For holiday parties and special events, a sequined midi skirt paired with a cashmere sweater creates that perfect balance of sparkle and comfort. The combination feels festive yet appropriate for cooler weather.
IV. Creative Layering Solutions
These outfits master the art of autumn layering with skirts as the foundation.
10. The Skirt and Over-the-Knee Boots

A shorter A-line skirt paired with over-the-knee boots creates a fashionable look that’s also practical for cooler weather. The boots provide warmth and make the outfit appropriate for autumn while showing just a hint of skirt.
11. The Maxi Skirt and Leather Jacket

A flowing maxi skirt paired with a fitted leather jacket creates an edgy-yet-feminine contrast that’s perfect for autumn. The jacket provides warmth and structure while the skirt maintains comfort and movement.
12. The Tulle Skirt and Sweater

A tulle midi skirt layered over opaque tights and paired with a chunky sweater creates a playful, fashionable look. The combination of delicate tulle with a cozy sweater is unexpectedly chic and perfect for autumn.

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Emily’s Pro Tips for Autumn Skirt Success
- Choose the Right Length: Mid-length skirts (just below the knee to mid-calf) are often most flattering and practical for autumn. They allow for boot wearing and work with various top lengths.
- Consider Proportion: Balance fuller skirts with more fitted tops, and slimmer skirts with slightly looser tops to create harmonious proportions.
- Invest in Quality Tights: Opaque tights in neutral colors extend your skirt wearability into cooler weather while providing comfort and coverage.
- Play with Textures: Autumn is the perfect time to mix textures like wool, corduroy, velvet, and leather in your skirt outfits.
- Define Your Waist: Use belts, tucked-in tops, or naturally waist-defining skirt styles to highlight your smallest point and create flattering curves.
Find Your Perfect Skirt Silhouette
Different skirt styles work beautifully for different body types:
- A-line skirts are universally flattering, balancing hips and highlighting waists
- Pencil skirts celebrate curves and create powerful silhouettes
- Wrap skirts offer adjustable fit and beautiful drape
- Full skirts create beautiful volume and movement
- Asymmetrical skirts add fashion-forward interest

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Embrace Your Autumn Skirt Style
Remember, the most important thing is how your skirt outfit makes you feel. When you find styles that make you feel confident and comfortable, you’ll naturally radiate beauty and poise. Autumn is the perfect season to experiment with different skirt styles, textures, and layering techniques until you find what works best for your body and personal style.
Which of these plus size autumn skirt outfits are you most excited to try? Are you a midi skirt devotee or a maxi skirt enthusiast? Share your own skirt style creations with our community over on Pinterest. Tag @chicseasonstyle so we can see your amazing autumn looks and share the inspiration!