21 Plus Size Fall Winery Outfits Curvy Women Will Love

Plus size fall winery outfits that actually work? Yes, and they’re easier to style than you think when you know these secrets.

You know that feeling when you’re scrolling through Pinterest, dreaming about those perfect vineyard photos? The ones where everyone looks effortlessly chic sipping wine among autumn leaves?

I used to think those looks were impossible for my curvy body. Boy, was I wrong.

Here’s the thing about winery fashion that nobody talks about. Most style guides completely ignore our real bodies and real needs. They forget we want comfort for walking vineyard paths.

They skip the part about looking put-together without feeling restricted. And don’t get me started on how they assume one size fits all when it comes to fall layering.

I’ve spent years perfecting the art of wine tasting outfits. Through trial and plenty of fashion errors, I’ve discovered what actually works.

The secret isn’t about hiding your curves or following rigid rules. It’s about understanding how to dress your beautiful body for the vineyard setting.

Fall winery visits are pure magic. The crisp air, golden leaves, and that perfect glass of wine. You deserve to feel confident and comfortable while creating those Instagram-worthy moments.

Whether you’re planning a casual afternoon at a local vineyard or a mid-day autumn wine tour, the right outfit makes all the difference.

Must-See: Plus Size Simple Fall Outfits.

21 Plus Size Fall Winery Outfits

Ready to discover 21 stunning plus size fall winery outfits that’ll have you looking and feeling amazing?

These aren’t just pretty pictures. They’re real, wearable looks for real women. Don’t forget to check out our styling tips section at the end for extra insider secrets.

22. Plus Size Fall Burgundy Velvet Midi Dress Winery Outfit

You’ll turn heads in this rich burgundy velvet midi dress paired with cognac leather ankle boots and a delicate gold chain necklace. The velvet fabric adds luxury while the midi length keeps you comfortable for vineyard walking.

Complete the look with a structured tan crossbody bag and subtle gold stud earrings that won’t interfere with wine tasting.

21. Plus Size Fall Chunky Knit Sweater Denim Winery Outfit

Layer a cream chunky knit sweater over dark wash high-waisted jeans with brown leather ankle boots. Add a camel-colored wool fedora and a leather statement belt to define your waist.

This cozy combination works perfectly for casual vineyard visits while maintaining that effortless autumn sophistication you’re looking for during outdoor wine tastings.

20. Plus Size Fall Olive Maxi Dress Wide-Brim Hat Winery Outfit

Choose an olive green maxi dress with three-quarter sleeves paired with nude block heel sandals and a matching wide-brim felt hat. Layer a lightweight beige cardigan for temperature changes and add a woven crossbody bag.

The earthy tones complement vineyard surroundings beautifully while the maxi length photographs gorgeously against autumn backdrops and rolling hills.

19. Plus Size Fall Mustard Cardigan Neutral Winery Outfit

Style a mustard yellow open-front cardigan over a cream fitted tank with tan ponte pants and cognac ankle boots. Add a delicate pearl necklace and carry a structured leather handbag in matching cognac.

This warm color palette echoes fall foliage while the neutral base keeps the look grounded and sophisticated for upscale winery visits.

18. Plus Size Fall Leather Jacket Sweater Winery Outfit

Combine a black leather moto jacket with a soft gray cashmere sweater, dark skinny jeans, and black combat boots with buckle details. Add silver hoop earrings and a black crossbody bag with chain details.

This edgier approach to winery fashion works especially well for younger wine enthusiasts who want attitude with their autumn vineyard adventures.

17. Plus Size Fall Earth Tones Midi Dress Winery Outfit

Wear a rust-colored midi dress with a camel blazer, nude tights, and brown suede ankle boots with a slight heel. Style with a delicate gold bracelet and matching earrings, plus a structured leather tote in matching brown.

The warm earth tones create a cohesive autumn look that photographs beautifully against vineyard landscapes and wine barrels.

16. Plus Size Fall Cozy Textures Sweater Dress Winery Outfit

Select a taupe cable-knit sweater dress with cognac over-the-knee boots and a matching leather belt to cinch the waist. Add a cream infinity scarf and carry a woven tote bag with leather handles.

The textural elements create visual interest while maintaining comfort for long tasting sessions and vineyard walks throughout the day.

15. Plus Size Fall Burgundy Cardigan Denim Winery Outfit

Layer a burgundy open cardigan over a white fitted tee with medium wash straight-leg jeans and tan suede ankle boots. Add a delicate gold necklace and carry a crossbody bag in matching tan.

This classic combination feels effortless yet polished, perfect for casual vineyard hopping where you want to look put-together without appearing overdressed.

14. Plus Size Fall Mustard Sweater Hat Winery Outfit

Pair a mustard yellow crew neck sweater with black skinny jeans, brown ankle boots, and a black wide-brim hat. Add a brown leather crossbody bag and gold statement earrings for polish.

The pop of mustard brightens the outfit while black and brown neutrals keep it grounded and vineyard-appropriate for autumn wine country adventures.

13. Plus Size Fall Olive Cardigan Ankle Boots Winery Outfit

Style an olive green long cardigan over a cream fitted tank with dark wash jeans and cognac ankle boots with block heels. Add a delicate layered necklace and carry a structured handbag in matching cognac leather.

The military-inspired olive shade pairs beautifully with autumn vineyard colors while maintaining sophisticated appeal for wine tasting events.

12. Plus Size Fall Tan Sweater Dress Leather Jacket Winery Outfit

Combine a tan ribbed sweater dress with a cropped brown leather jacket, black tights, and black ankle boots with gold hardware. Add gold hoop earrings and a black crossbody bag with chain details.

This combination balances cozy autumn textures with edgier leather elements, perfect for evening wine tastings or indoor winery events.

11. Plus Size Fall Burgundy Midi Dress Chunky Knit Winery Outfit

Layer a cream chunky knit cardigan over a burgundy midi dress with cognac knee-high boots and a matching leather belt. Add pearl drop earrings and carry a woven tote with leather trim.

The rich burgundy echoes wine themes while cream and cognac accessories create a sophisticated color story for upscale vineyard visits.

10. Plus Size Fall Earth Tones Sweater Denim Winery Outfit

Wear a rust-colored crew neck sweater with medium wash boyfriend jeans, brown suede ankle boots, and a camel wool hat. Style with a brown leather crossbody bag and gold layered bracelets.

The warm earth tone palette complements autumn vineyard settings while the relaxed fit jeans ensure comfort during full-day wine country explorations.

9. Plus Size Fall Neutral Cardigan Maxi Dress Winery Outfit

Choose a beige maxi dress with a cream long cardigan, tan ankle boots, and a matching wide-brim felt hat. Add a brown leather belt to define the waist and carry a structured tote bag.

The tonal neutral palette creates an effortlessly elegant look that photographs beautifully against vineyard backdrops while ensuring comfort throughout the day.

8. Plus Size Fall Mustard Midi Dress Boots Winery Outfit

Style a mustard yellow midi dress with a brown leather jacket, black tights, and black knee-high boots with buckle details. Add a black fedora and matching crossbody bag for polish.

The unexpected mustard and black combination creates visual interest while maintaining autumn appropriateness for wine country visits and outdoor tasting events.

7. Plus Size Fall Olive Sweater Wide-Brim Hat Winery Outfit

Pair an olive green turtleneck sweater with tan wide-leg pants, cognac ankle boots, and a matching wide-brim hat. Add gold statement earrings and carry a leather crossbody bag in cognac.

The military-inspired olive creates an unexpected twist on autumn dressing while maintaining sophistication appropriate for upscale winery experiences and photo opportunities.

6. Plus Size Fall Burgundy Sweater Dress Hat Winery Outfit

Select a burgundy sweater dress with cognac ankle boots, a matching leather belt, and a brown felt fedora. Style with gold layered necklaces and carry a structured leather handbag.

The rich burgundy creates wine-inspired elegance while cognac accessories add warmth and sophistication perfect for autumn vineyard visits and wine tasting sessions.

5. Plus Size Fall Tan Cardigan Ankle Boots Winery Outfit

Combine a tan open-front cardigan with a cream fitted tee, olive green skinny jeans, and cognac ankle boots with block heels. Add a delicate bracelet and carry a crossbody bag in matching cognac leather.

The unexpected olive and tan combination creates an earthy palette perfect for blending with vineyard surroundings during autumn wine tours.

4. Plus Size Fall Neutral Sweater Leather Jacket Winery Outfit

Layer a cropped black leather jacket over a cream crew neck sweater with tan straight-leg pants and black ankle boots. Add silver jewelry and carry a black structured handbag with gold hardware.

This edgier take on neutral dressing works perfectly for evening wine events or indoor tastings where you want sophistication with attitude.

3. Plus Size Fall Earth Tones Maxi Dress Winery Outfit

Choose a rust-colored maxi dress with three-quarter sleeves, paired with cognac knee-high boots and a matching leather belt. Add a cream infinity scarf and carry a woven tote bag with leather handles.

The warm earth tones create a cohesive autumn look while the maxi length provides elegance and comfort for vineyard walking.

2. Plus Size Fall Mustard Cardigan Midi Dress Winery Outfit

Style a mustard yellow long cardigan over a black midi dress with brown ankle boots and a matching wide-brim hat. Add gold statement earrings and carry a brown leather crossbody bag.

The bold mustard creates unexpected sophistication against the black base while brown accessories ground the look in autumn vineyard appropriateness.

1. Plus Size Fall Olive Sweater Dress Chunky Knit Winery Outfit

Wear an olive green sweater dress with a cream chunky knit vest, cognac over-the-knee boots, and a matching leather belt. Style with gold layered necklaces and carry a structured handbag in cognac leather.

The layered knit textures create visual interest while the olive and cream combination maintains sophisticated elegance for upscale winery experiences.

10 Step Styling Tips For Plus Size Fall Winery Outfits

1. Start with the Right Foundation Layer

Your foundation sets the tone for everything else. I always begin with a well-fitted bra that gives me the support I need for a day of walking around vineyards.

Trust me, nothing ruins a wine tasting faster than constantly adjusting yourself. Look for seamless options under fitted tops or go for a wireless bra with good coverage under flowy pieces.

Your undergarments should make you feel secure and confident. I learned this the hard way during a particularly windy day in Napa when my ill-fitting bra made every photo session uncomfortable.

The right foundation means you can focus on enjoying the wine instead of worrying about wardrobe malfunctions.

Remember, comfort starts from the inside out, and when you feel supported, it shows in your posture and confidence.

2. Master the Art of Layering Without Bulk

Fall layering can be tricky for us curvy women. The key is choosing pieces that add warmth without adding bulk around your midsection.

I start with a fitted base layer, then add a structured cardigan or blazer that hits at the most flattering part of my torso. Avoid bulky sweaters that hide your shape completely.

Instead, opt for cardigans that can be left open to create vertical lines. A lightweight scarf adds texture and interest without overwhelming your frame. Think about proportions here.

If you’re wearing a flowy top, balance it with more fitted bottoms. The goal is creating a silhouette that feels intentional, not accidental.

I’ve found that investing in quality layering pieces makes all the difference in how polished you look.

3. Choose Fabrics That Move with Your Body

Vineyard visits involve walking, sitting, and yes, lots of wine glass lifting. Your fabrics need to work with you, not against you. Jersey knits, ponte fabrics, and pieces with a bit of stretch are your best friends.

Avoid anything too stiff or structured that might dig in when you sit down for that long wine tasting session. I love how ponte pants feel like leggings but look like dress pants.

Cotton blends breathe well during those unexpectedly warm fall afternoons. Stay away from fabrics that wrinkle easily since you’ll be sitting and standing frequently.

Natural fibers mixed with a small percentage of elastane give you the best of both worlds. The last thing you want is feeling restricted when you’re trying to relax and enjoy yourself.

Your clothes should feel like a second skin, not a costume.

4. Embrace the Power of a Well-Fitted Jacket

A great jacket can transform any outfit from basic to brilliant. For winery visits, I prefer structured blazers or denim jackets that hit at the hip or just below.

This length is universally flattering and creates a nice silhouette without cutting you in half. The jacket should fit smoothly across your shoulders and back without pulling or bunching.

If you can’t comfortably layer a thin sweater underneath, it’s too small. I have this amazing burgundy blazer that makes me feel like I belong in any upscale winery setting.

The color coordinates beautifully with fall foliage and wine barrels. A well-chosen jacket also gives you flexibility as temperatures change throughout the day.

You can start covered up in the morning and remove layers as the afternoon sun warms things up.

5. Select Bottoms That Flatter and Function

Your bottom half needs to handle walking on uneven vineyard terrain while looking effortlessly chic. High-waisted jeans or trousers create a smooth line and give you confidence to tuck in tops.

I’m obsessed with dark wash jeans that don’t show dirt from outdoor adventures. Wide-leg pants in flowing fabrics look elegant and photograph beautifully against vineyard backdrops.

Avoid anything too tight that might be uncomfortable after a few wine tastings and appetizers. The waistband should sit comfortably without digging in.

I learned to always do the “sit test” before buying pants. If they’re uncomfortable sitting in the dressing room, they’ll be miserable during a three-hour wine tasting.

Look for details like flat-front styling that creates clean lines without extra bulk around your hips and stomach area.

6. Find the Perfect Balance with Footwear

Vineyard terrain can be challenging, so your shoes need to be both stylish and practical.

I’ve made the mistake of wearing heels to outdoor wineries and spent the entire day wobbling on gravel paths. Low block heels or wedges with good grip work well for more formal winery events.

For casual vineyard hopping, I love ankle boots with a slight heel. They look put-together but provide the stability I need. Closed-toe shoes protect your feet from spills and outdoor elements.

Make sure whatever you choose, you can walk confidently for several hours. I always bring a backup pair of comfortable flats in my bag, just in case.

Your feet will thank you at the end of the day, and you’ll actually enjoy the experience instead of counting down minutes until you can sit down.

7. Accessorize with Purpose and Personality

Accessories can make or break your winery outfit, but the key is choosing pieces that enhance rather than overwhelm.

A statement necklace can elevate a simple sweater, while delicate earrings complement a busy patterned top. I love how a silk scarf tied around my neck adds sophistication to any look.

Sunglasses are essential for outdoor tastings, so invest in a pair that flatters your face shape. A crossbody bag keeps your hands free for wine glasses and photos.

Avoid anything too dangly or noisy that might interfere with your tasting experience. The goal is looking polished without appearing overdressed.

I’ve found that one standout accessory paired with more subtle pieces creates the most balanced look.

Remember, you want people noticing your radiant smile and confidence, not being distracted by competing accessories.

8. Shop Smart: Brands That Actually Understand Our Bodies

Finding the right pieces starts with shopping brands that design specifically for plus size women.

Torrid consistently delivers trendy pieces that fit well through the bust and hips. Lane Bryant offers classic styles that photograph beautifully at wineries.

ASOS Curve has incredible variety for different style preferences and budgets. Eloquii creates sophisticated pieces perfect for upscale wine country visits.

Target’s Ava & Viv line provides affordable basics that mix well with investment pieces. Online, I love Dia & Co for discovering new brands that work for my body type.

Don’t forget to check department stores like Nordstrom and Macy’s, which carry multiple plus size lines under one roof.

The key is finding brands that consistently fit your body well, then building your wardrobe around those reliable pieces. Quality over quantity always wins, especially for special occasion outfits like winery visits.

9. Consider Color Psychology and Photography

Colors play a huge role in how you feel and how you photograph against vineyard backdrops. Deep jewel tones like burgundy, emerald, and navy complement fall foliage beautifully.

Earth tones help you blend harmoniously with the natural winery setting. I avoid wearing all black because it can look harsh against the warm, golden tones of autumn vineyards.

Instead, I incorporate black as an accent color paired with warmer shades. Rich purples and deep reds echo the wine theme without being too literal.

Neutrals like cream, camel, and olive green photograph gorgeously and never look out of place. Think about the Instagram photos you want to create.

Will your outfit complement the scenery or compete with it?

I’ve learned that slightly muted colors often photograph better than bright, saturated ones because they don’t overpower the beautiful natural lighting you’ll find at most wineries.

10. Plan for Weather Changes and Comfort

Fall weather can be unpredictable, especially in wine regions with morning fog and afternoon sun. I always check the forecast and plan for temperature swings throughout the day.

Start with a base layer you’d be comfortable in during the warmest part of the day, then add pieces you can remove as needed.

A lightweight cardigan or wrap is perfect for transitioning between indoor tasting rooms and outdoor vineyard walks. Don’t forget about wind factor in open vineyard settings.

Your hair and clothes will move, so choose styles that look good even when slightly tousled. I pack a small emergency kit with hair ties, blotting papers, and lipstick for touch-ups between tastings.

Comfort should never be sacrificed for style, especially during a full day of wine tasting.

When you feel comfortable and prepared, you can fully enjoy the experience and focus on making beautiful memories instead of worrying about your outfit.

Final Thoughts

Creating the perfect plus size fall winery outfits isn’t just about clothes. It’s about claiming your space in those beautiful vineyard moments.

You deserve to feel radiant while sipping wine among autumn leaves. Every time you choose an outfit that makes you feel confident, you’re showing other curvy women it’s possible.

So go ahead, book that wine tour. Pack those gorgeous pieces we talked about.

Trust me, when you feel amazing in your own skin, the wine tastes better, the photos turn out stunning, and the memories become absolutely magical.