What to Wear to a Winery: 25 Chic Outfit Ideas

The first time I visited a winery, I remember standing in front of my closet for way too long. 

I wanted to look put together but also stay comfortable enough to enjoy a long afternoon sipping wine in the sun.

It was a spring day in Napa, and I ended up in a flowy midi dress with sandals—simple, but perfect. That day taught me that winery outfits don’t have to be over-the-top to feel stylish and confident.

I’ve since explored wineries across the country, from California to Virginia, and every time I go, I notice how much the right outfit can enhance the experience. 

You want something that feels relaxed yet polished, practical but pretty. 

This guide is for anyone wondering what to wear to a winery, whether it’s your first visit or your fifth. 

Inside, you’ll find 25 chic outfit ideas that strike the perfect balance between style and ease.

1. Flowy Midi Dress with Wedge Sandals

A midi dress is breezy and comfortable for walking through vineyards. Wedges give you a little height without sinking into the grass.

2. Linen Jumpsuit with a Straw Hat

A linen jumpsuit feels cool and effortless. Add a wide-brimmed hat to keep the sun off your face and complete the look.

3. White Jeans with a Printed Blouse

White jeans instantly elevate an outfit. Pair them with a light, patterned blouse for a clean and feminine look.

4. Wrap Dress with Espadrilles

A wrap dress flatters every body type and works for almost any winery setting. Espadrilles add a soft touch that feels timeless.

5. Maxi Skirt with a Fitted Tank

Maxi skirts are ideal for wine tastings—they move beautifully and feel romantic. A fitted tank keeps the outfit grounded.

6. Denim Dress with Ankle Boots

For fall or cooler days, a denim dress and ankle boots bring a bit of edge without feeling too heavy.

7. Cropped Wide-Leg Pants with a Button-Down Shirt

Wide-leg pants feel sophisticated but relaxed. Tuck in a button-down for a structured, put-together finish.

8. Floral Sundress with Flat Sandals

Floral dresses never go out of style at wineries. Flat sandals keep things casual while still feeling thoughtful.

9. Romper with a Crossbody Bag

A romper is playful and easy to wear. A crossbody bag lets you keep your hands free for holding wine glasses and snapping photos.

10. High-Waisted Shorts with a Flowy Top

If it’s warm out, high-waisted shorts and a lightweight top create a balanced, breezy silhouette.

11. Off-the-Shoulder Dress with Statement Earrings

Off-the-shoulder dresses bring a little drama in the best way. Pair with bold earrings and you’re good to go.

12. Monochrome Outfit with Gold Jewelry

Choose one color head-to-toe and accessorize with simple gold pieces. It’s clean, easy, and always looks polished.

13. Midi Skirt with a Knit Tee

A knit tee tucked into a printed midi skirt feels casual but stylish. Add sneakers or low sandals for extra comfort.

14. Shirt Dress with a Belt

Shirt dresses give you a relaxed fit but can be cinched at the waist to add definition. They’re also easy to dress up or down.

15. Cargo Pants with a Fitted Crop Top

For a cool and laid-back look, cargo or utility pants paired with a simple crop top feel fresh and functional.

16. Slip Dress with a Lightweight Cardigan

Slip dresses are sleek and breathable. A cardigan gives you an extra layer if the breeze picks up.

17. Chambray Top with White Shorts

Chambray and white is a classic summer combo that always feels crisp. This outfit works well for both indoor and outdoor tastings.

18. Tiered Mini Dress with Sunglasses

A tiered mini dress adds texture and movement. Don’t forget oversized sunglasses to complete the winery-ready look.

19. Matching Set with Minimal Sandals

Co-ord sets are simple but stylish. Look for soft fabrics and neutral tones for an elevated vibe.

20. T-shirt Dress with a Denim Jacket

If you’re going casual, a t-shirt dress is a no-fail option. Throw a denim jacket over your shoulders for that easygoing look.

21. Midi Dress with a Slit and Straw Bag

A slit adds just a bit of flair to a longer dress. A straw bag ties in perfectly with a vineyard setting.

22. Wide-Brim Hat with a Casual Maxi Dress

When in doubt, go for a wide-brim hat. It instantly makes any maxi dress look more styled and gives you extra sun protection.

23. Knotted Blouse with a Midi Skirt

Knotting your blouse at the waist adds shape and personality. It’s a great way to refresh basics you already own.

24. Structured Romper with Heeled Sandals

Choose a romper with clean lines for a more refined feel. Heeled sandals dress it up without sacrificing comfort.

25. Flared Jeans with a Boho Blouse

If you’re leaning into a relaxed, earthy look, flared jeans and a boho-style blouse feel effortlessly cool.

Final Thoughts

Wineries have a way of making you want to slow down and savor the moment, and your outfit should reflect that energy. 

It’s not about dressing up too much—it’s about finding that sweet spot where you feel confident, comfortable, and ready to enjoy good wine and good company.

I’ve worn versions of all these outfits over the years, and each one brings something different to the experience. 

Whether you’re headed to a vineyard in Sonoma or a countryside winery close to home, these ideas will help you show up in style—without overthinking it.