Hello my dears, Emily here! Picture this: golden sunlight filtering through fiery leaves, a crisp breeze carrying the scent of earth and grapes, and you, looking and feeling absolutely fabulous with a glass of wine in hand. A fall winery visit is one of life’s simple pleasures, but figuring out what to wear can sometimes feel more complicated than choosing between a Cabernet or a Merlot!
For us curvy women, the perfect winery outfit needs to strike a delicate balance. It should be comfortable enough for walking between vines, polished enough for photos and a potentially upscale setting, and adaptable enough for shifting fall temperatures. But most importantly, it should make you feel confident and beautiful.
After years of sipping and styling, I’ve curated 15 plus size fall winery outfits that blend practicality with undeniable chic. Let’s find a look that lets you focus on the wine tasting, not your outfit.
Why Winery Style Matters for Curvy Women
Winery fashion combines elegance and comfort in a way that naturally complements curves. The autumn setting calls for:
- Rich fabrics like velvet, ponte knit, and soft jerseys that drape beautifully
- Layered silhouettes that allow for temperature regulation while creating flattering shapes
- Earthy color palettes that complement both the season and diverse skin tones
- Sturdy yet stylish footwear that can handle uneven terrain without sacrificing style
Your Winery Style Playbook: 15 Curated Looks
I. Elegant Dresses for Sophisticated Sipping
Velvet Midi Dress Magic
A burgundy or emerald velvet midi dress offers luxurious comfort and elegance. The rich fabric drapes beautifully over curves while feeling seasonally appropriate. Pair with cognac ankle boots and minimal gold jewelry for a look that photographs beautifully against autumn foliage.
Sweater Dress Comfort
A belted sweater dress in taupe or oatmeal provides both warmth and style. The knit fabric offers stretch and comfort, while the belt defines your waist. Style with over-the-knee boots and a sleek crossbody bag for sophisticated warmth.
Earth Tone Maxi Romance
A flowy maxi dress in rust or olive green combines romance and practicality. The long sleeves and length provide warmth, while the flowing silhouette moves gracefully through vineyard rows. Accent with a wide-brim hat and layered necklace for bohemian charm.
Wrap Dress Classic
The timeless wrap dress creates a flattering V-neckline and cinches at your smallest point. Choose autumn-inspired prints or solid jewel tones for effortless elegance that works in any winery setting.
II. Chic Separates for Versatile Style
Knit and Denim Duo
Pair a cream or mustard chunky knit sweater with dark wash, high-waisted jeans. Add a statement leather belt to define your silhouette and complete with brown ankle boots. This classic combination offers both comfort and style.
Statement Cardigan Layer
Use a long, open-front cardigan in burgundy or mustard as your outfit’s centerpiece. Layer over a fitted tank and pair with ponte pants or skinny jeans. This versatile option allows easy adjustment as temperatures change throughout your visit.
Leather Jacket Edge
Add contemporary flair with a faux leather moto jacket layered over a cashmere-style sweater. Pair with dark skinny jeans for chic warmth that transitions seamlessly from daytime tasting to evening festivities.
Blazer Polish
A well-tailored blazer elevates any winery outfit. Wear over a shell top or lightweight sweater with your best-fitting jeans for smart-casual sophistication that works for both tasting and dinner.
III. Trend-Forward Ensembles
Shacket and Wide-Leg Comfort
The shirt-jacket hybrid, or shacket, in plaid or herringbone pattern layers perfectly over basic tees. Pair with comfortable wide-leg jeans and Chelsea boots for trendy relaxation that handles changing temperatures with ease.
Faux Leather Leggings Elegance
Elevate comfort with faux leather leggings paired with a knee-length tunic or oversized sweater. The leggings add sophistication while the tunic provides coverage and comfort for extended tasting sessions.
Jumpsuit Simplicity
A stylish jumpsuit in flowing fabric offers one-piece sophistication. Choose styles with defined waistlines or add your own belt for flattering shape that makes dressing effortless while maintaining polish.
IV. Essential Winery Accessories
The Perfect Hat
A wool fedora or wide-brimmed hat provides both style and function. It completes your autumn aesthetic while offering sun protection and photographic appeal.
Statement Boots
Ankle boots with block heels or knee-high boots provide stability on uneven terrain while maintaining style. Choose suede or leather in neutral tones like cognac or black for versatility.
Crossbody Convenience
A hands-free crossbody bag keeps essentials accessible while leaving hands free for wine glasses. Structured leather or woven designs add rustic charm while maintaining practicality.
Cozy Scarf Wrap
A lightweight infinity scarf or pashmina adds color and texture while serving as practical protection against cool breezes. Drape elegantly or use as a wrap when temperatures drop.
Emily’s Pro Tips for Winery Visits
Footwear First
Choose wedge heels, block heels, or flat booties with sturdy soles over stilettos that sink into grass. Comfortable footwear ensures you enjoy the entire experience without foot pain.
Fabric Choices
Select seasonally appropriate textures like velvet, corduroy, ponte knit, and quality wools that drape beautifully on curves while providing adequate warmth.
Waist Definition
Always define your waist through belts, tailoring, or strategic tying to create flattering silhouettes that highlight your curves.
Layering Strategy
Implement lightweight layers that can be easily added or removed as temperatures fluctuate throughout your visit. This ensures comfort during both outdoor vineyard walks and indoor tastings.
Your Perfect Winery Experience
Remember that confidence is your most attractive accessory. Whether you choose a cozy sweater dress or a chic jumpsuit, wear it with self-assurance and enjoy your day surrounded by beautiful scenery and excellent company.
Which of these plus size fall winery outfits speaks to your personal style? Share your favorite winery looks and styling tips with our community over on Pinterest by tagging @chicseasonstyle. Let’s inspire each other to savor every moment of this beautiful season in style!
