21 Plus Size Dressy Fall Outfits Curvy Women Will Love

Plus size dressy fall outfits shouldn’t be about hiding… they should be about celebrating every gorgeous curve while staying effortlessly chic this autumn season.

Listen, I’ve been there. Standing in my closet, staring at the same old rotation of safe pieces, wondering why “dressy” always felt like code for “boring” when you’re plus size.

But here’s what I’ve learned after years of trial, error, and some truly fabulous discoveries: fall is actually our secret weapon season.

Think about it. While others are scrambling to layer summer pieces, we get to embrace rich textures, luxurious fabrics, and sophisticated silhouettes that were practically designed for curves.

A tailored blazer over a stylish blouse? Pure magic. Those wide-leg pants that make you feel like you’re gliding? They’re having a moment, and so are we.

The truth is, dressy fall fashion isn’t about following rules… it’s about breaking them with confidence.

Whether you’re heading to a semi-formal wedding, planning the perfect date night look, or need something polished for that dinner party, autumn gives us permission to be bold.

We’re talking rich burgundies, deep emeralds, and textures that catch the light just right.

From casual Friday elegance to full-on formal glamour, the key is understanding that classy doesn’t mean conservative.

Sometimes it’s about pairing unexpected pieces… like those gorgeous heels with a flowing dress that moves with you, not against you.

Must-See: Plus Size New York Fall Outfits.

21 Plus Size Dressy Fall Outfits

Ready to transform your fall wardrobe? Don’t forget to check out our styling tips at the end for all the insider secrets that’ll have you feeling absolutely unstoppable this season.

22. Plus Size Velvet Blazer and Leather Leggings Dressy Fall Outfit

You’ll command attention in a rich burgundy velvet blazer paired with high-waisted faux leather leggings.

The structured blazer creates definition while the sleek leggings elongate your legs beautifully. Add pointed-toe ankle boots in black patent leather and a delicate gold chain necklace.

This sophisticated combination works perfectly for gallery openings or upscale dinner dates where you want to look effortlessly chic.

21. Plus Size Midi Skirt and Turtleneck Dressy Fall Outfit

A pleated midi skirt in deep emerald paired with a fitted cream turtleneck creates timeless elegance.

The high-waisted skirt accentuates your waist while the turtleneck provides sophisticated coverage. Complete the look with cognac leather knee-high boots and a structured handbag in matching brown.

This polished ensemble transitions seamlessly from office meetings to evening cocktail parties with absolute grace and confidence.

20. Plus Size Wide-Leg Trousers and Silk Blouse Dressy Fall Outfit

Chocolate brown wide-leg trousers in crepe fabric paired with a champagne silk blouse create luxurious sophistication.

The high-waisted trousers define your silhouette while the silk blouse adds elegant texture contrast. Finish with nude block heels and gold hoop earrings for refined glamour.

This combination works beautifully for formal business dinners or sophisticated social events where you need to look polished and professional.

19. Plus Size Sweater Dress and Statement Coat Dressy Fall Outfit

A fitted camel sweater dress layered under a structured wool coat in navy creates sophisticated warmth.

The ribbed sweater dress hugs your curves while the tailored coat adds architectural interest. Add tall suede boots in matching camel and a silk scarf for luxurious finishing touches.

This elegant combination works perfectly for autumn weddings or upscale brunch events where comfort meets refined style.

18. Plus Size Pencil Skirt and Cashmere Sweater Dressy Fall Outfit

A high-waisted pencil skirt in charcoal paired with a fitted cashmere sweater in blush pink creates feminine sophistication.

The structured skirt emphasizes your curves while the soft sweater adds luxurious texture. Complete with pointed-toe pumps in black patent and pearl drop earrings.

This polished look works beautifully for important presentations or dinner parties where you want to look professionally elegant and approachable.

17. Plus Size Palazzo Pants and Fitted Top Dressy Fall Outfit

Wide palazzo pants in navy crepe paired with a fitted long-sleeve top in ivory create effortless elegance.

The high-waisted pants create beautiful proportions while the fitted top balances the silhouette perfectly. Add wedge heels in nude and a delicate tennis bracelet for sophisticated finishing touches.

This combination works wonderfully for semi-formal events or date nights where you need comfort without sacrificing style.

16. Plus Size Shift Dress and Tailored Blazer Dressy Fall Outfit

A long-sleeve shift dress in forest green paired with a fitted blazer in cream creates polished sophistication.

The structured dress skims your body beautifully while the contrasting blazer adds professional polish. Complete with ankle boots in brown leather and a structured tote bag.

This versatile combination transitions effortlessly from office environments to after-work networking events with confidence and style.

15. Plus Size Culottes and Silk Camisole Dressy Fall Outfit

High-waisted culottes in black paired with a silk camisole in dusty rose create modern elegance.

The wide-leg culottes provide comfort while maintaining sophisticated proportions. Layer with a cropped cardigan in matching black and add block heels in nude.

This contemporary look works perfectly for art gallery openings or sophisticated dinner dates where you want to look fashion-forward and polished.

14. Plus Size Maxi Skirt and Fitted Sweater Dressy Fall Outfit

A pleated maxi skirt in burgundy paired with a fitted mock-neck sweater in cream creates romantic sophistication.

The high-waisted skirt creates beautiful proportions while the fitted sweater balances the silhouette perfectly. Add ankle boots with a slight heel and delicate gold jewelry.

This elegant combination works beautifully for autumn celebrations or dinner parties where you want to look feminine and refined.

13. Plus Size A-Line Skirt and Button-Down Shirt Dressy Fall Outfit

A knee-length A-line skirt in camel paired with a crisp white button-down creates classic sophistication.

The structured skirt flatters your silhouette while the tailored shirt provides timeless elegance. Add knee-high boots in matching camel and a structured blazer for added polish.

This refined combination works beautifully for business meetings or upscale social events where traditional elegance is appreciated.

12. Plus Size Jumpsuit and Statement Cardigan Dressy Fall Outfit

A fitted jumpsuit in charcoal paired with a longline cardigan in mustard creates contemporary elegance.

The tailored jumpsuit creates beautiful proportions while the open cardigan adds sophisticated layering. Complete with heeled ankle boots and geometric jewelry in gold.

This modern look works perfectly for gallery openings or dinner parties where you want to look fashion-forward and effortlessly chic.

11. Plus Size Cropped Pants and Tunic Blouse Dressy Fall Outfit

High-waisted cropped pants in black paired with a silk tunic in jewel blue create polished sophistication.

The cropped length shows off your shoes while the tunic provides elegant coverage. Add pointed-toe heels in nude and a delicate chain necklace.

This versatile combination works beautifully for upscale lunch dates or evening cocktail parties where you need comfort without sacrificing refined style.

10. Plus Size Midi Dress and Structured Jacket Dressy Fall Outfit

A sleeveless midi dress in deep wine paired with a structured jacket in cream creates sophisticated contrast.

The fitted dress hugs your curves while the tailored jacket adds professional polish. Complete with knee-high boots in cognac and gold stud earrings.

This elegant combination works perfectly for business dinners or formal events where you need to look polished and professionally appropriate.

9. Plus Size Flare Pants and Fitted Blouse Dressy Fall Outfit

High-waisted flare pants in forest green paired with a fitted blouse in ivory create retro-inspired elegance.

The flare silhouette creates beautiful proportions while the fitted top balances the look perfectly. Add platform heels in nude and a vintage-inspired clutch.

This sophisticated combination works wonderfully for dinner parties or date nights where you want to look uniquely stylish and confidently feminine.

8. Plus Size Pencil Dress and Longline Coat Dressy Fall Outfit

A fitted pencil dress in navy paired with a longline coat in camel creates executive elegance.

The structured dress emphasizes your curves while the tailored coat adds sophisticated layering. Complete with pointed-toe pumps in black and a structured handbag.

This polished look works beautifully for important business meetings or formal events where you need to project confidence and professional authority.

7. Plus Size Bootcut Pants and Silk Shell Dressy Fall Outfit

High-waisted bootcut pants in chocolate brown paired with a silk shell in champagne create timeless sophistication.

The bootcut silhouette flatters your legs while the silk top adds luxurious texture. Add heeled boots in matching brown and delicate pearl jewelry.

This classic combination works perfectly for upscale restaurant dinners or semi-formal events where elegant simplicity is most appropriate.

6. Plus Size Wrap Skirt and Fitted Sweater Dressy Fall Outfit

A knee-length wrap skirt in plaid paired with a fitted sweater in solid burgundy creates preppy sophistication.

The wrap style accentuates your waist while the fitted sweater balances proportions beautifully. Complete with ankle boots in brown leather and a structured tote bag.

This polished look works wonderfully for autumn lunches or casual business meetings where approachable elegance is key.

5. Plus Size Cigarette Pants and Embellished Top Dressy Fall Outfit

Slim cigarette pants in black paired with an embellished top in gold create evening elegance.

The fitted pants create sleek proportions while the embellished details add glamorous sparkle. Add pointed-toe heels in metallic gold and statement earrings.

This sophisticated combination works perfectly for cocktail parties or special dinner dates where you want to look polished and appropriately festive for the occasion.

4. Plus Size Accordion Skirt and Cashmere Cardigan Dressy Fall Outfit

A pleated accordion skirt in navy paired with a fitted cashmere cardigan in cream creates refined sophistication.

The structured skirt creates beautiful movement while the luxury cardigan adds elegant warmth. Complete with low-heeled pumps in nude and a silk scarf.

This polished look works beautifully for afternoon tea or upscale shopping events where classic elegance and comfort are equally important.

3. Plus Size Straight Skirt and Cowl Neck Top Dressy Fall Outfit

A high-waisted straight skirt in burgundy paired with a cowl neck top in ivory creates sophisticated elegance.

The structured skirt emphasizes your waist while the draped neckline adds feminine softness. Add knee-high boots in black and delicate gold jewelry.

This refined combination works perfectly for dinner parties or date nights where you want to look elegantly polished and romantically appealing.

2. Plus Size Trouser Suit and Silk Camisole Dressy Fall Outfit

A tailored trouser suit in charcoal paired with a silk camisole in blush creates executive sophistication.

The structured jacket and pants create professional proportions while the silk camisole adds feminine softness. Complete with pointed-toe heels in black and a structured briefcase.

This polished look works beautifully for important business presentations or formal networking events where professional authority is essential.

1. Plus Size Culotte Jumpsuit and Fitted Cardigan Dressy Fall Outfit

A culotte jumpsuit in forest green paired with a fitted cardigan in cream creates modern sophistication.

The wide-leg silhouette provides comfort while maintaining polished proportions. Add block heels in nude and geometric jewelry in gold.

This contemporary look works perfectly for art gallery events or upscale brunches where you want to look fashion-forward and effortlessly elegant.

Must-See: Plus Size Fall Vest Outfits.

11 Helpful Styling Tips For Plus Size Dressy Fall Outfits

1. Master the Art of Layering Without Looking Bulky

Here’s the thing about layering that nobody tells you: it’s not about adding more clothes, it’s about adding the right clothes.

I used to think layering meant throwing on a cardigan and calling it a day. Wrong! Start with a fitted base layer—think a sleek bodysuit or thin knit top. Then add structure with a blazer or jacket that nips in at the waist.

The magic happens when you choose pieces that complement your silhouette rather than compete with it. A flowing kimono over a structured dress? Perfection. A cropped jacket over a longer tunic? Chef’s kiss.

The key is creating visual interest while maintaining your natural waistline. Remember, layers should enhance your curves, not hide them under a pile of fabric.

2. Embrace the Power of Monochromatic Dressing

Monochromatic doesn’t mean boring… it means sophisticated. When I wear all black or all navy, something magical happens.

I look taller, more polished, and honestly? More expensive. But here’s where it gets interesting: texture is your secret weapon.

Pair a matte crepe blouse with glossy leather pants. Mix a chunky knit sweater with sleek ponte leggings.

The same color family creates a seamless line from head to toe, while different textures add depth and visual intrigue. Don’t be afraid to play with shades within the same color family either.

A burgundy blazer over a wine-colored dress with oxblood boots? That’s not matching—that’s mastery.

Trust me, once you start thinking in color stories rather than individual pieces, your entire wardrobe will feel more cohesive and intentional.

3. Invest in Statement Accessories That Actually Make Statements

Accessories can make or break an outfit, but they shouldn’t whisper… they should sing. I’m talking about pieces that draw the eye exactly where you want it.

A bold statement necklace can transform a simple sweater into dinner-party worthy attire.

But here’s what I’ve learned: bigger isn’t always better. Sometimes it’s about choosing pieces with incredible craftsmanship or unique details.

A structured handbag in a rich cognac leather, a pair of earrings that catch the light just right, or a belt that creates the perfect waist definition… these are the pieces that elevate everything else.

The trick is balancing scale with your outfit. If you’re wearing a busy pattern, let your accessories be more subtle. If your outfit is simple, that’s when you can go bold with your accessories.

4. Find Your Perfect Fit Formula for Pants and Bottoms

Let’s talk about the holy grail: pants that actually fit. After years of settling for “good enough,” I finally cracked the code.

High-waisted wide-leg pants are having a moment for a reason… they’re universally flattering and incredibly versatile. But here’s the secret: the rise matters more than the style.

Find the point on your torso where you feel most confident, then shop accordingly. For me, it’s about two inches above my natural waist.

Some days it’s high-waisted trousers with a tucked-in blouse. Other days it’s palazzo pants with a fitted top. The key is understanding your proportions and working with them.

Don’t be afraid to get things tailored either. A $15 hem can make a $50 pair of pants look like they cost $200. Trust me on this one… proper fit is worth every penny.

5. Master the Art of Choosing Flattering Necklines

Necklines are like picture frames for your face, and choosing the right one can change everything.

I used to avoid V-necks because someone told me they were “too revealing.” What nonsense! A well-placed V-neck elongates the neck and creates a beautiful vertical line.

But here’s what I’ve discovered: it’s not just about the shape, it’s about the depth. A shallow V-neck on a blouse can look professional and polished. A deeper V on a sweater can look sophisticated and intentional.

Scoop necks are incredibly flattering because they mirror the natural curve of your shoulders. Boat necks can make your shoulders look broader in the best way.

The key is trying different styles and paying attention to how they make you feel. When you feel confident, it shows in how you carry yourself.

6. Build a Capsule of Versatile Dress Styles

Dresses are the ultimate one-and-done pieces, but not all dresses are created equal. I’ve learned to invest in styles that can transition from day to night with just a few tweaks.

A midi dress in a rich jewel tone can go from office appropriate with a blazer to date-night ready with statement jewelry.

Wrap dresses are universally flattering because they create a defined waist and accommodate different body shapes beautifully.

A-line dresses in ponte or jersey fabrics are comfortable enough for all-day wear but polished enough for evening events. The key is choosing dresses in fabrics that drape well and colors that work with your existing wardrobe.

When you find a dress silhouette that works for you, don’t be afraid to buy it in multiple colors or patterns. Life’s too short for ill-fitting dresses.

7. Navigate Plus Size Brand Shopping Like a Pro

Shopping for plus size dressy fall outfits used to feel like a treasure hunt, but now? The options are incredible.

Brands like Eloquii, Lane Bryant, and Torrid have really stepped up their game with sophisticated pieces that don’t compromise on style.

For higher-end options, I love Universal Standard and 11 Honoré—they carry extended sizes from luxury designers. Online, ASOS Curve and Nordstrom have amazing selections with detailed size charts and customer reviews.

Here’s my pro tip: sign up for newsletters and follow these brands on social media. They often announce sales and new arrivals first to their subscribers.

Also, don’t overlook department stores like Macy’s and Nordstrom Rack—they’re carrying more plus size designer pieces than ever before.

The key is knowing your measurements and reading reviews from other customers with similar body types.

8. Create Perfect Color Palettes for Fall Sophistication

Fall colors are like nature’s own mood board, and they’re incredibly flattering for dressy occasions. Rich burgundies, deep forest greens, warm caramels, and sophisticated navies create an instant sense of elegance.

But here’s what I’ve learned: it’s not just about following trends, it’s about finding colors that make your skin look radiant.

I used to avoid certain colors because they weren’t “my season,” but then I realized that the right shade of any color can work if you choose it thoughtfully.

A rich plum might be more flattering than a bright purple. A warm cognac might work better than a cool brown. The key is testing colors near your face and paying attention to how they make you look and feel.

When you find your perfect fall palette, building outfits becomes so much easier because everything coordinates beautifully.

9. Balance Proportions with Strategic Styling Choices

Proportion is everything in fashion, but it’s not about making yourself look smaller… it’s about creating visual harmony.

I used to think that meant wearing loose, shapeless clothes, but that actually made me look larger than I was. The secret is understanding how different silhouettes work together.

A fitted top with wide-leg pants creates a beautiful balance. A flowing tunic with skinny jeans does the same thing in reverse.

The key is avoiding the matchy-matchy trap where everything is the same level of fitted or loose.

Create contrast by mixing structured pieces with softer ones, or fitted pieces with flowing ones. This creates visual interest and helps define your silhouette in the most flattering way possible.

10. Perfect Your Shoe Game for Fall Elegance

Shoes can make or break a dressy fall outfit, and I’ve learned that comfort doesn’t have to mean sacrificing style.

A good pair of ankle boots with a modest heel can work with everything from dresses to pants. Pointed-toe flats in rich fall colors add sophistication without the height.

For special occasions, a kitten heel or wedge provides elevation without the pain of a stiletto. Here’s my secret: invest in quality shoes in neutral colors that work with multiple outfits.

A great pair of black leather boots, cognac flats, and navy heels can carry you through an entire season.

Pay attention to details like hardware, stitching, and materials… these small touches make a big difference in how expensive your outfit looks. And never underestimate the power of a good sole insert for all-day comfort.

11. Master the Art of Seasonal Transitioning

Fall fashion is all about transition pieces that work as temperatures change throughout the day. I’ve learned to think in layers that can be easily added or removed.

A light cardigan over a sleeveless dress works for cool mornings and can be tied around your waist when it warms up.

A blazer over a short-sleeve top provides structure and warmth without being too heavy. The key is choosing pieces that look intentional whether you’re wearing them or carrying them.

Scarves are perfect for this… they add warmth and style but can be easily tucked into a bag when you don’t need them. Think about your daily routine and choose pieces that adapt to different environments.

The goal is looking polished from morning coffee to evening dinner without having to completely change your outfit.

Final Thoughts

Here’s the truth about plus size dressy fall outfits: they’re not about conforming to someone else’s idea of what we should look like. They’re about celebrating who we are right now, in this moment, in these bodies.

I’ve watched too many beautiful women wait for someday… someday when they’re smaller, someday when they’re more confident, someday when they have the perfect wardrobe.

But someday is today. Fall is here, and you deserve to feel absolutely stunning in every single outfit you choose.

Your curves aren’t something to hide or apologize for… they’re your signature, your strength, your story. So go ahead, embrace those rich textures and bold colors. You’ve got this.