24 Plus Size Fall Winery Outfits Curvy Women Will Love

Plus size fall winery outfits are all about combining cozy layers, flattering silhouettes, and stylish pieces that feel effortless for a day out among the vines. Think soft sweaters, midi skirts, tailored jackets, and ankle boots that balance comfort with seasonal charm.

Fall is the perfect season for winery looks because layers and rich textures create dimension and keep you warm during crisp afternoons. The right outfits let you enjoy tastings and strolls through the vineyard while looking polished and comfortable.

In this post, you’ll find 24 outfit ideas curated for curvy women who want fall-ready winery styles. From casual daytime ensembles to chic brunch-ready looks, these outfits focus on flattering fits, wearable layers, and easy ways to embrace autumn elegance.

24 Plus Size Fall Winery Outfits

1. Plaid Shacket + Black Denim Balance

Bold orange plaid jumps out first, rich, warm, and touchably soft, almost like brushed flannel you’d pull on before a cool vineyard stroll. Color and pattern feel lively without overwhelming the shape.

Black denim gives steady contrast, creating clean vertical lines that flatter curves without effort. Silhouette feels easy, grounded, and perfect for sipping wine outdoors, relaxed but still put-together in that quietly confident way.

2. Tie-Front Sundress + Soft Button Skirt Flow

Crisp white fabric catches the light beautifully, giving an easy, airy drape that feels fresh even against early-fall vines. Tie-front detail adds subtle structure while keeping the neckline open and relaxed.

Skirt falls gently from the bust, creating movement that flatters curves without clinging. Silhouette feels quietly confident, comfortable for sipping wine and wandering rows, yet still polished in that understated, vineyard-ready way.

3. Cutout Denim Set + Flared Jean Shape

Deep denim immediately stands out, sturdy, saturated, and shaped to follow curves with intention. Cutout detailing adds playful structure, giving the top a modern edge that still feels grounded in classic fabric.

Flared jeans balance proportions beautifully, bringing length through legs while keeping everything smooth at the waist. Outfit feels bold but wearable, perfect for fall winery days when you want something confident, sculpted, and uniquely your vibe.

4. Gingham Crop Set + Tiered Skirt Ease

Red gingham catches your eye right away, crisp, textured, and full of that charming picnic-meets-vineyard energy. Cutout hem on the top adds gentle structure, giving the pattern a little modern twist.

Tiered skirt brings soft movement that feels friendly on curves, skimming instead of clinging. Proportions sit nicely together, creating an outfit that feels playful yet relaxed, something you’d reach for on a warm fall afternoon among the vines.

5. Chunky Knit Vest + Ribbed Sweater Dress

Chunky knit layers instantly catch the eye, adding a cozy, tactile weight that feels made for crisp vineyard days. Ribbed olive sweater dress underneath shapes the figure with subtle structure, keeping everything sleek yet warm.

Wide belt draws the waist in just right, balancing out the softness of the knit. Paired with tall boots, the whole look leans effortlessly polished and fall-ready without trying too hard.

6. Mustard Cable Cardigan + Wrap Mini Dress

Chunky mustard cardigan makes a bold entrance, its thick weave adding warmth and a cozy fall texture. Black wrap mini dress underneath drapes softly, letting the knit stand out while keeping the overall shape light and fluid.

Loose waist tie brings gentle definition, letting curves breathe without losing shape. Paired with lace-up boots, the mix of soft knit and structured details hits that perfect sweet spot between relaxed and pulled together.

7. Rust Midi Dress + Infinity Scarf

Warm rust fabric flows with a soft, structured weight that moves beautifully as you walk. Midi length lands perfectly at the calf, giving that classic fall ease while still feeling refined and pulled together.

Wide belt brings shape without overpowering, letting curves sit naturally in the spotlight. Tall boots ground everything with an earthy finish, making the outfit feel polished yet effortless for a day at the vineyard.

8. Leather Moto Jacket + Wide-Leg Trousers

Supple leather adds instant edge, bringing structure and shine against soft knit texture. Cropped jacket hits at just the right spot, sharpening the lines and creating a confident, tailored finish.

Wide-leg trousers drape beautifully, moving with ease while keeping proportions balanced. Neutral tones keep everything grounded, making the outfit feel modern, elevated, and perfect for a breezy afternoon among the vines.

9. Rust Duster Cardigan + Olive Leggings

Rust-toned cardigan flows softly with a touch of texture that instantly warms up the look. Longline length creates that easy layered effect, giving movement while keeping everything feeling intentionally put together.

Olive leggings hug the shape without squeezing, pairing effortlessly with the loose striped blouse. Earthy shades blend beautifully, striking a comfy but polished balance perfect for a vineyard stroll.

10. Burgundy Sweater Dress + Statement Belt

Ribbed knit hugs every curve with a smooth, structured stretch that feels both warm and elevated. Midi length adds a polished finish, while the rich burgundy shade pairs effortlessly with earthy fall tones.

Wide belt cinches the waist just right, shaping a clean hourglass line without overpowering. Ankle boots and structured bag complete the look, giving vineyard style a refined, timeless twist.

11. Chunky Olive Sweater + Relaxed Trousers

Chunky knit sweater adds an easy, soft texture that instantly reads cozy. Slight slouch through the shoulders gives movement, keeping everything feeling unfussy yet elevated for a fall day out.

Relaxed trousers sit comfortably at the waist, skimming the body without clinging. Rolled hems and suede boots ground the look beautifully, bringing just the right mix of structure and ease.

12. Mustard Midi Dress + Leather Jacket

Bold mustard knit pulls the eye in immediately, hugging curves with a smooth stretch that feels confident and vibrant. Rich brown leather layers over top, adding sleek structure that sharpens the silhouette without weighing it down.

Fitted cut keeps everything clean and intentional, while tall boots elongate the line from waist to hem. Warm autumn tones tie the whole look together, striking a perfect balance of bold color and classic texture.

13. Textured Cardigan Coat + Belted Midi Dress

Soft knit cardigan coat brings instant warmth and texture, draping effortlessly with a gentle weight that feels plush and inviting. Open front keeps the movement easy, creating that cozy-luxe layering moment perfect for cool evenings.

Belted dress defines the waist beneath all that softness, shaping a clean silhouette without losing comfort. Tall boots and warm neutrals tie everything together, making the look feel relaxed yet beautifully intentional.

14. Cable Knit Sweater + Dark Denim

Rich burgundy knit stands out immediately, its cable texture adding cozy depth that feels made for crisp fall vineyard walks. Cropped cut hits at the perfect spot, creating shape without losing that relaxed, easy vibe.

Dark denim balances the softness of the sweater, hugging the figure with just enough structure. Warm-toned boots and a textured bag pull everything together, keeping the look grounded yet vibrant in the autumn light.

15. Chunky Knit Cardigan + Burgundy Dress

Open-knit cardigan adds a soft, relaxed layer that moves easily with every step. Its chunky texture feels warm and inviting, making the outfit instantly cozy without overwhelming the shape underneath.

Burgundy dress brings clean lines and a hint of structure, keeping the silhouette balanced and flattering. Tall boots finish the look with polish, giving that perfect vineyard stroll vibe.

16. Tan Sweater Dress + Moto Jacket

Soft knit dress draws attention with its subtle pattern and easy drape, creating a smooth line that flatters without clinging. Short hem adds a playful touch while still keeping the overall look clean and polished.

Fitted moto jacket sharpens the silhouette, adding just the right amount of edge. Dark tights and suede boots ground the outfit beautifully, striking a balance between warm neutrals and structured layering.

17. Olive Cardigan Coat + Skinny Jeans

Thick knit cardigan instantly stands out, its longline shape adding a soft, cozy frame that flows easily as you move. Textured weave gives depth, making the outfit feel layered and warm without being heavy.

Skinny jeans balance that volume, highlighting shape while keeping everything streamlined. Ankle boots anchor the look, blending earthy tones into a polished, easygoing winery outfit that feels both chic and comfortable.

18. Mustard Grape Knit Sweater + Dark Denim

Playful knit brings instant charm, its thick mustard yarn adding warmth and bold personality. Grape motif gives the outfit a fun vineyard twist, while the slightly oversized cut frames the body with an easy, cozy drape.

Dark denim keeps the look grounded and clean, balancing the sweater’s texture with a simple line. Structured leather tote ties everything together, making the outfit feel thoughtful yet effortlessly laid-back.

19. Burgundy Chunky Cardigan + Cropped Denim

Deep burgundy cardigan catches the eye with its plush, oversized texture, creating a cozy frame that moves softly with each step. Length adds drama without feeling heavy, wrapping the look in warm autumn layers.

Cream sweater and fitted denim keep the shape balanced, letting the cardigan take center stage. Suede boots and a structured bag ground everything, giving that perfect mix of softness and polish.

20. Belted Knit Dress + Oversized Scarf

Soft knit dress flows with a gentle weight that hugs in all the right places. Grey tone sets a calm, classic base, letting texture shine through without feeling busy or heavy.

Wide tan belt defines the waist beautifully, pulling the look together with structure. Chunky scarf and tall boots layer in warmth, creating a balanced, cozy outfit that feels both refined and inviting.

21. Textured Blazer + Midi Skirt Set

Warm, earthy tones instantly draw the eye, with soft knit meeting structured layers in such an elegant way. Cropped sweater and flowing midi skirt create movement that feels effortless yet pulled together.

Tailored blazer shapes the frame, grounding the softness with clean lines. Ankle boots and a structured tote complete the look, blending vintage charm with modern polish that fits perfectly into a vineyard backdrop.

22. Studded Leather Jacket + Charcoal Sweater

Sleek leather jacket brings a cool, structured edge that contrasts perfectly with the softness of the knit underneath. Cropped cut sharpens the waist, creating strong lines without losing comfort or ease.

Charcoal sweater sits effortlessly against dark denim, keeping the palette moody and modern. Studded boots tie everything together with a bold finish, making the whole outfit feel powerful yet wearable.

23. Mustard Chunky Cardigan + Cream Dress

Golden mustard knit brings instant warmth, its chunky texture wrapping the frame in cozy softness. Loose sleeves and an open front give the outfit movement, making it feel relaxed but still put-together.

Cream dress underneath adds a clean, easy line that softens the bold knit. Neutral tones and simple layering let the cardigan shine, creating a warm fall look that feels effortless and elevated.

24. Olive Midi Dress + Cozy Cardigan

Olive fabric flows with an easy drape, catching light softly and moving beautifully with each step. Light knit cardigan layers over top, adding warmth and texture without interrupting the clean lines of the dress.

Loose silhouette feels relaxed yet polished, giving room to breathe while still framing the figure gently. Straw accessories and warm tones make the whole look feel perfectly effortless for a sunny fall afternoon.

The Ultimate Guide to Plus Size Fall Winery Outfits

Welcome back to [TrendiHair], where style meets confidence, and today, we’re serving you the perfect blend of chic, cozy, and curve-flattering looks for a gorgeous day at the winery. Think warm autumn tones, romantic textures, elevated casual layers, and silhouettes that make you feel effortlessly elegant as you sip, stroll, and snap pictures among the vines.

Fall winery outfits are flattering for plus-size bodies because they lean into:

• Soft, drapey fabrics that skim the curves
• Waist-defining silhouettes
• Layering that adds polish without bulk
• Rich fall colors that complement every skin tone

These looks work beautifully for:

• Hourglass shapes wanting defined waists
• Apple shapes who love flowy tops + structured layers
• Pear shapes who shine in A-line skirts and balanced proportions
• Rectangle shapes seeking curve-creating pieces like wrap dresses

The best part? Winery fashion blends comfort with sophistication, perfect for photos, tastings, and fall breezes.

Step-by-Step Styling Guide: Creating the Perfect Plus Size Fall Winery Outfit

1. Start With a Romantic, Figure-Flattering Base

Your base piece should feel polished but comfortable.

Great Options

• Wrap dresses
• Midi sweater dresses
• Flowy blouses paired with jeans
• Ribbed knit tops
• Off-shoulder sweaters

Fit Tips

• Wrap silhouettes are universally flattering for plus-size curves.
• Choose tops that skim rather than cling for a polished finish.

💡 Pro Tip:
Vertical ribbing or a wrap neckline naturally elongates your torso and highlights your shape.

2. Choose Chic, Comfortable Bottoms

Winery style is laid-back luxe, your bottoms should reflect that.

Great Picks

• High-waisted dark jeans
• A-line or pleated midi skirts
• Faux leather leggings
• Straight-leg trousers

Fit Tips

• High-rise fits define the waist and smooth the midsection.
• A-line skirts balance wider hips beautifully.

💡 Pro Tip:
If wearing pants, choose ankle-length styles to show off cute fall boots.

3. Add a Polished Fall Layer

Chilly breezes + winery views? Layering is key.

Ideal Layers

• Long cardigans
• Trench coats
• Lightweight shackets
• Suede or faux leather jackets
• Tailored blazers

Layering Tips

• Choose hip- or thigh-length layers for the most flattering shape.
• Avoid overly bulky knits; medium-weight layers drape better.

💡 Pro Tip:
For a defined waist, belt your cardigan or choose a jacket with subtle shaping.

4. Pick Winery-Perfect Shoes

Comfort is important—winery terrain can be uneven.

Best Shoe Styles

• Block-heel ankle boots
• Tall riding boots
• Ballet flats
• Loafers
• Low wedges

Fit Tips

• Block heels give height without sinking into grass.
• Wide-width boots keep you comfortable all day.

💡 Pro Tip:
Taupe, brown, burgundy, or black boots blend beautifully with fall palettes.

5. Accessorize With Elevated, warm-Toned Pieces

Accessories complete the winery vibe, think soft, cozy, luxe.

Great Accessory Options

• Felt wide-brim hats
• Gold hoops or layered necklaces
• Leather crossbody or saddle bags
• Printed scarves
• Oversized sunglasses

Styling Tips

• Stick to warm metals (gold, rose gold) for a rich fall feel.
• Use one statement accessory, like a hat or chunky necklace, to elevate your look.

💡 Pro Tip:
Long scarves or necklaces create vertical lines that elongate your silhouette naturally.

❓ Frequently Asked Questions (FAQ)

1. How do I avoid looking bulky with fall layers?

• Choose medium-weight fabrics instead of heavy knits.
• Belt your cardigan or choose structured outerwear for shape.
• Pair flowy pieces with fitted ones to balance the silhouette.

2. What fabrics are most flattering for plus-size winery outfits?

Opt for fabrics that drape beautifully and flatter curves:

• Soft knits
• Jersey
• Chiffon
• Ponte
• Faux suede
• Lightweight wool blends

These create movement without adding unnecessary volume.

3. Can petite plus-size women wear winery-ready fall outfits?

Absolutely!

Try:

• Knee-length or midi dresses that don’t overwhelm your frame
• Cropped or hip-length outer layers
• Monochromatic or tonal outfits for elongation
• Block heels or ankle boots for subtle height

4. How do I pick the right accessories without doing too much?

• Choose a color palette (warm neutrals, gold, burgundy).
• Pick one star piece (hat, scarf, or statement earrings).
• Keep everything else minimal and coordinated.

Final Thoughts

Plus size fall winery outfits are all about feeling beautiful, polished, and comfortable while soaking in the seasonal magic. From wrap dresses to chic boots and cozy layers, you have endless ways to create a stunning vineyard-ready look that celebrates your curves.