What to Wear to a Winery, According to a Fashion Pro

You may have your order at a vineyard down pat—I like an ice-cold glass of rosé with a charcuterie board to munch on while I yap, for example—but knowing what to wear to a winery isn’t always so clear.

That’s because there typically is no hard and fast dress code. A quick look at the website should help you decode whether a wine cellar is dressy or the kind of place where a T-shirt is totally appropriate. However, wardrobe stylist Danielle Cafiero’s offers this advice: “Easy, breezy is always a winning formula for vineyard dressing,” she tells Glamour. The expert points to relaxed silhouettes, like maxi skirts and shift dresses as great options. The goal, of course, is to find “a look that aligns with a day of wine tasting and cheese grazing.” Put another way, what will you feel comfortable in but still look good in all the photos you’ll inevitably be taking?

Glamour’s winery styling wish list

The Floral Dress: J.Crew Embroidered Apron Dress, $200
The Trendy Sandals: Yishaweiqi Ankle-Strap Flat Sandals, $40
The Statement Vest: Ann Taylor Long Crewneck Vest, $129
The Easy Dress: Grace Karin Casual Smocked Dress, $44
The Printed Skirt: Wayf Josefina Skirt, $79
The Elevated T-Shirt: Treasure & Bond Ruched Muscle Tee, $24
The Jelly Flats: VorisVina Jelly Mesh Ballet Flats, $45

Since a day at the vineyard is meant to be fun, the setting is also a perfect fashion playground—a safe place to experiment with seasonal trends and wear something outside your normal day-to-day. The current nautical aesthetic that’s taking over the fashion industry, for instance, will feel right at home in wine country. Toss on a long-sleeve striped top and accessorize with a seashell-adorned necklace and boat shoes. Or, if this season’s boho look is more your speed, slip into a gauzy sheer number and finish with strappy sandals.

Something else to keep in mind: Be practical with your shoes. If you think you might end your wine tour by frolicking through the nearby fields and capturing photos of the gorgeous vineyard views, comfort is king. Swap your high heels for a feel-good flat, sturdy ankle boots, or a teeny-tiny pump. “Whatever you do, stay away from wearing stilettos,” Cafiero advises. “The grapevines are the only things we want rooted in the soil.”

Below, set your sights on eight chic winery outfit formulas made for Napa Valley and beyond.

A Breezy Mini + Strappy Sandals

You can’t beat a floral mini dress for a winery outing, especially one with a comfortable loose silhouette. After all, you never know how many hours you’ll spend in the tasting room (no one really ever wants to leave). Swap the heels pictured here for more sensible strappy sandals, however. Accessorize with a woven bag, and you’re all set for Sonoma.

Courtesy of brand

Farm Rio Pineapple Tapestry Studded Dress

$348

Nordstrom

Courtesy of brand

Yishaweiqi Ankle-Strap Flat Sandals

$50

Amazon

A Cute Blouse + Skirt

A day of wine tasting should fit in with your personal style—so if a cute blouse and skirt sounds more like you than a dress, go for it! A minimal white off-the-shoulder top looks especially punchy with an eye-catching striped maxi skirt. Tie everything together with a black leather mule, a crossbody bag, and perhaps a wide-brimmed hat to protect your skin from the sun.

Courtesy of brand

J.Crew Cap-Sleeve Lace-Trim Top

$98

J.Crew

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Boden Full Poplin Maxiskirt

$185

Boden

Mixed Patterns

Calling all maximalists! I bet you’ll have a hard time resisting this print-heavy (and serotonin-boosting) look. When mixing patterns, it helps to choose two motifs in the same color scheme to avoid looking too outlandish. You’ll stand out in every group photo taken during your winery visit. A denim jacket can help anchor the look if you’re nervous about going all in with patterns.

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Zara Gingham Cropped Top

$40

Zara

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Wayf Josefina Skirt

$79

Nordstrom

All White (Yes, Really)

Not sure what to wear to a winery? When in doubt, reach for summer whites no matter what time of year it is. My favorite wine tasting outfit is a basic tank top with a flowy maxi skirt in neutral colors. The separates don’t necessarily need to match, either—a stark white and eggshell combo can feel fresh yet still refined. However, if you’re prone to spills, I’d suggest skipping red wine and sticking to chardonnay.

Courtesy of brand

Treasure & Bond Ruched Muscle Tee

$40 $24

Nordstrom

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Madewell Pleated Midi-Skirt

$128

Madewell

A Floral Midi Dress

If you get a last-minute invite to a wine tasting experience, don’t panic about what to wear. A floral midi dress is one of those pieces you can pretty much guarantee will work anywhere, and a vineyard is no exception. Because the look is statement-making on its own, simply accessorize with dainty necklaces and understated ballet flats (and sunscreen!). A light jacket is a wise addition to the outfit as well if the weather is on the chillier side.

Courtesy of brand

J.Crew Embroidered Apron Dress

$248 $200

J.Crew

Courtesy of brand

VorisVina Jelly Mesh Ballet Flats

$45

Amazon

A Pair of Jeans + A Statement Vest

Wondering how to spice up your everyday denim? A linen pastel vest, like this salmon-colored style here, won’t disappoint. We love how this iteration boasts beads for a touch of playfulness. Earn extra fashion points by styling the outfit with a summery straw bag and beachy seashell earrings. If this is a winter winery visit, add a button-down top underneath the best or go for a blazer instead.

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Ann Taylor Long Crewneck Vest

$129

Ann Taylor

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Madewell Dean Jeans

$148

Madewell

Loafers + A Shirt Dress

Loafers may not first spring to mind when mapping out your winery outfit, but don’t overlook the silhouette. A chunky black leather style plays well with a printed shirt dress and is the perfect outfit for looking cute while staying comfortable. Here’s an extra style tip: A belt, be it skinny or thick, has the power to transform any ensemble.

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Boden Amy Cotton Midi Shirtdress

$190

Boden

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G.H. Bass Weejuns Whitney Loafers

$175

Nordstrom

$175

Free People

The Minimalist Dress

A LWD always reads sophisticated and put together, despite the look requiring little to no effort. If the winery’s environment is laid-back, tone down the sundress with black flip-flops. All the look is missing is a roomy handbag (in case you’re tempted to bring home a souvenir from the gift shop) and a soft cardigan.

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