Whenever I visit a winery, I like to combine style with comfort so I can enjoy the day fully. There is something special about walking through the vines, taking in the scenery, and feeling confident in my outfit.

Dressing for a winery is about choosing clothes that match the beauty of the place while allowing you to move with ease.

In this guide, I am sharing my favorite winery outfit ideas to help you decide exactly what to wear to a winery. You will find options for different seasons and occasions, from relaxed afternoons to more refined events.

If you are planning a simple tasting or a special celebration, these ideas will help you look polished and feel comfortable from the first sip to the last.

Styling Basics Before Choosing Your Winery Outfit

A great winery outfit combines style, comfort, and versatility so you can enjoy the day without fuss. Start with fabrics that feel light yet refined, such as linen, cotton, silk, or soft knits, which work well in most settings.

Opt for silhouettes that allow movement while maintaining a polished appearance, think wrap dresses, tailored trousers, or jumpsuits.

Footwear should be stylish but functional, like block heels, wedges, or chic flats that handle uneven paths.

Keep accessories purposeful, such as a wide-brimmed hat, light jewelry, or a crossbody bag for essentials. Choose colors inspired by nature or muted patterns that complement vineyard scenery.

The aim is to look effortless while still appearing thoughtfully dressed.

With these basics in mind, you can pick the right pieces from the following winery outfit ideas to suit any occasion

Casual Daytime Winery Outfit Ideas

Daytime winery visits need stylish, comfortable outfits suitable for tours, tastings, or relaxed patio lunches. Light fabrics, comfy shoes, and subtle accessories keep you looking polished and relaxed.

1. Flowy Midi Dress with Sandals

A flowy midi dress adds comfort with grace, making it perfect for daytime winery visits. Lightweight fabrics and soft prints create a relaxed, vineyard-inspired look.

Pair with low-heeled sandals for comfort, a crossbody bag for essentials, and sunglasses for style and protection.

This versatile outfit works well for wine tastings, casual lunches, or scenic strolls through the vineyard, allowing you to look polished while staying comfortable during the entire day.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

2. Linen Jumpsuit with Woven Accessories

A linen jumpsuit offers effortless style and breathability, making it an excellent choice for long, winery days. Neutral tones provide versatility, while woven sandals and a straw tote give a vineyard-inspired touch.

This outfit works well for tours, casual lunches, or tastings.

It keeps you cool and comfortable while looking stylish, blending in with the winery’s setting without feeling too dressed up.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

3. High-Waisted Shorts with Blouse

High-waisted shorts paired with a flowy blouse make a chic, relaxed winery outfit. The shorts keep you cool, while the blouse adds polish. Flat sandals or espadrilles keep the look comfortable and stylish.

This pairing is perfect for outdoor tastings, casual lunches, or vineyard picnics. The high waistline elongates the legs, and the loose blouse allows for easy movement.

It’s a refined yet easygoing choice for warm winery days, balancing comfort with subtle style.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

4. Maxi Skirt with Fitted Top

A maxi skirt paired with a fitted top creates a balanced silhouette perfect for winery days. The flowing skirt moves gracefully, while the top keeps the look structured.

Sandals or wedges complete the outfit for style and comfort. This look works for casual afternoon visits, photo sessions, or semi-formal tastings.

Its versatility makes it easy to layer or accessorize, keeping you comfortable and confident for any winery visit.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

Graceful Evening or Special Event Winery Outfits

Evening tastings call for refined style. These outfits mix comfort with class, from silk to tailored pieces, keeping you polished and confident for special winery events.

5. Tailored Trousers with Statement Top

Tailored trousers paired with a bold blouse create a polished, approachable style for winery visits. Lightweight fabrics keep you comfortable, while loafers or block heels offer structure and stability.

A structured handbag finishes the look, ideal for moving from casual tastings to formal dinners.

This outfit balances class and practicality, ensuring you remain stylish without compromising comfort, whether seated at a wine bar or walking through vineyard paths.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

6. Shirt Dress with Belt

A belted shirt dress is a versatile winery pick. Its relaxed fit adds comfort, while the belt gives shape. Pair with wedges or boots for a polished, easy look.

This outfit transitions easily from daytime tastings to evening dinners without needing a change. The collared neckline adds structure, and the length offers modest coverage while remaining feminine.

Its adaptability makes it a dependable choice for all-day winery outings that require style and practicality.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

7. Wrap Dress with Block Heels

A wrap dress offers timeless style and comfort, making it perfect for winery outings. The adjustable design flatters all body types, while lightweight fabrics keep you comfortable.

Block heels add comfort and height, while a crossbody bag offers ease. The outfit works for tastings and formal events.

The wrap style also allows for easy movement, whether strolling through vineyards or sitting at a tasting table, making it both practical and chic for any winery visit.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

Warm-Weather Winery Outfits

Spring and summer winery visits call for light fabrics, airy silhouettes, and comfy footwear. These outfits keep you cool and stylish for sunny tastings and vineyard strolls.

8. Off-Shoulder Sundress with Espadrilles

An off-shoulder sundress offers romance and comfort in one winery-ready look. Soft colors or airy prints harmonize with vineyard surroundings, while wedge espadrilles add flattering height without sacrificing comfort.

A woven bag completes the look, perfect for outdoor tastings, picnics, or casual celebrations.

Its feminine charm works beautifully for photos, creating an effortless blend of casual refinement ideal for sunny days in scenic winery locations.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

9. Midi Wrap Skirt with Tank Top

A midi wrap skirt paired with a fitted tank top creates an airy, stylish winery look. The wrap adds flow, the tank keeps it sleek, and espadrilles or sandals finish the relaxed look.

This pairing works well for outdoor events, tastings, or warm-weather winery visits. The adjustable skirt makes it comfortable for long days, while its feminine cut ensures you look polished in photos.

It’s a go-to choice for a casual yet thoughtfully styled vineyard appearance.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

10. Jumpsuit with Belted Waist

A belted jumpsuit is a one-and-done solution for winery style. The belt defines your waist, creating a tailored look, while the relaxed fit ensures comfort. Pair with mules or sandals for a chic finish.

This outfit is adaptable for both casual day trips and polished evening tastings. Its simplicity invites accessories like a scarf or bold earrings, letting you customize the look.

The one-piece design makes dressing easy, while the belt keeps it flattering and structured all day

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

11. Wide-Leg Pants with Sleeveless Blouse

Wide-leg pants paired with a sleeveless blouse offer effortless grace for winery outings. The loose silhouette keeps you comfortable, while the blouse adds structure. Wedges or heeled sandals complement the style.

Perfect for upscale tastings, events, or wine garden afternoons, this outfit combines modern style with lasting comfort.

The fluid lines of the pants create graceful movement, making it a flattering choice for walking through vineyards or sipping wine on a terrace.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

Cool-Weather Winery Outfits

Autumn and winter winery trips call for warm layers, rich colors, and comfy shoes. These outfits suit tastings, walks, or gatherings, mixing practicality with style for colder months.

12. Knit Sweater with Midi Skirt

A knit sweater tucked into a midi skirt is an ideal choice for cooler winery days. Opt for a skirt with movement, such as pleats or a bias cut, for a soft, feminine shape.

Suede ankle boots introduce seasonal texture, while a leather bag and subtle jewelry complete the outfit.

This pairing offers warmth without sacrificing style, making it suitable for autumn vineyard walks, indoor tastings, or cozy wine lounges, combining comfort and class in one effortlessly stylish ensemble.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

13. Pleated Midi Skirt with Blouse

A pleated midi skirt with a blouse delivers feminine grace for winery settings. The pleats add movement and visual interest, while the blouse keeps it refined. Pair with ankle boots or flats for a balanced look.

Perfect for day-to-night transitions, this outfit works equally well for wine tours, tastings, and evening events.

The textured skirt looks great in vineyard photos, making it a favorite for winery visits where memories matter as much as the wine.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

14. Cropped Pants with Button-Up Shirt

Cropped pants with a crisp button-up shirt create a smart, casual winery style. Light fabrics allow easy movement, while loafers or block heels add polish.

A crossbody or tote bag adds functionality. This look fits winery tours, tastings, or lunches. Its tailored yet relaxed style easily transitions from sunny patios to indoor lounges.

The combination of structure and comfort ensures you’ll remain stylish while feeling completely at ease all day.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

15. Paperbag Waist Pants with Fitted Top

Paperbag waist pants with a fitted top create a flattering, modern silhouette. The cinched waist adds definition, while the fitted top balances the proportions. Sandals or block heels finish the look with style.

This outfit is perfect for casual tastings, patio lunches, or even semi-formal events. It’s easy to accessorize with light jewelry or a statement bag, allowing it to work across different winery settings.

The combination of comfort and refinement makes it a wardrobe staple for vineyard visits.

• Fabric Choice: Select breathable cotton or viscose for warm days.
• Prints & Colors: Soft florals or muted tones blend with vineyard views.

Accessorizing Your Winery Look for Style and Comfort

Accessories can take your winery outfit from simple to standout while keeping comfort in mind. The right additions enhance your style and make the day more enjoyable.

• Statement Hat: A wide-brim hat offers sun protection and flatters your face in vineyard photos.
• Light Jewelry: Minimal gold or silver jewelry adds polish without overpowering and stays lightweight.
• Stylish Sunglasses: Sunglasses protect from glare and add style. Choose frames that suit your face shape.
• Functional Bag: A medium-sized crossbody bag keeps essentials close and hands free.
• Light Scarf: A thin scarf adds texture and can double as light coverage. It’s perfect for breezy vineyard afternoons.
• Comfortable Footwear: Block heels or wedges keep you stylish yet stable on uneven ground. They also ensure comfort for extended walking.

Tips for Choosing the Perfect Winery Outfit

The right winery outfit combines style, comfort, and practicality so you can enjoy the day without worry. Keep these tips in mind to make sure you look great and feel comfortable from your first glass to your last sip.

• Prioritize Comfort: Choose breathable fabrics for easy movement and all-day ease.
• Mind the Footwear: Opt for stylish yet stable shoes like wedges, block heels, or flats.
• Stick to Versatile Colors: Neutral or earthy tones suit vineyards and simplify accessorizing.
• Balance Fit and Flow: Mix fitted and relaxed pieces for structure with comfort.
• Layer Smartly: Light layers adjust easily to indoor and outdoor settings.
• Consider the Occasion: Dress to match the winery’s vibe and event type.

Conclusion

Visiting a winery is as much about the atmosphere as it is about the wine, and the right outfit can help you enjoy both.

Comfort and style should go together, whether walking the vineyard, tasting, or at an evening event.

I still remember one afternoon when I wore a breezy linen jumpsuit with sandals, which kept me cool during the vineyard walk and polished enough for the dinner that followed.

Choosing breathable fabrics, balanced silhouettes, and practical shoes makes the day smoother.

With these ideas, you’ll feel confident and comfortable, ready to enjoy everything from casual tastings to special celebrations, savoring each sip with ease and style.