What to Wear to a Winery (Do's and Don'ts + Stylish Wine Tasting Outfits)

Essential rules and ensembles to make your next wine tasting trip unforgettable

From the breathtaking landscapes of Napa Valley, California to the enchanting scenery of Finger Lake, New York, there are so many magical places to show off your wine tasting outfits. Whether you want to sip a divine pinot in the spring or toast champagne at a winter wedding, we’ll help you put together the perfect wardrobe. If you’re ready to make the vineyard your runway, then enjoy our guide to looking sumptuous and delicious at any winery you find yourself.

This article is based on an interview with our personal stylist and image consultant, Cassandra Sethi, founder of Next Level Wardrobe. Check out the full interview here.

Things You Should Know

  • Make sure you stay comfy. For example, wear practical shoes, like dressy sandals, chunky heels, or slingback mules so you can explore the whole winery.
  • Go for more sophisticated ensembles, like a flowy blouse, a midi skirt, and ankle boots, since wine tasting is a classy affair.
  • Dress for the season. For example, wear a blouse tucked in shorts with beaded sandals in the summer. In the winter, slip on a knitted puff sleeve dress and boots.
  • If you attend a wedding at a winery, steer clear of white and go for dresses in different shades, like jewel tones, solid colors, or pastel shades.
Section 1 of 6:

Dress Code

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    Wear something sophisticated and dressy. If you’re a little unsure what to wear, reach for the sophisticated staples in your wardrobe. For example, instead of a T-shirt, try on a flowy blouse. Give your flip-flops a pass and go straight for your dressier footwear. Accessorize your ensemble with dainty jewelry to provide a touch of class to the outing.[1]
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    Wear comfortable shoes. While stilettos are pretty, it’s easy for them to get stuck on dirt paths or grass. In order to make sure you get the most out of your experience and see all the sights, choose practical footwear like dressy sandals, chunky heels, or slingback mules.[2]
    • Opt for low-maintenance outfits. For example, moisturize and use a chilled eye cream before you leave so you glow all day.
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    Try on outfits that are low-maintenance so you can move around a lot. Make it effortless to impress—choose dresses, tops, and bottoms that are simple to slip on. Steer clear of outfits that take a lot of time to lace up or have hard-to-reach zippers. Also leave the rompers at home. With all the wine you’ll be drinking, you’ll probably want ensembles that are easy to deal with.[3]
    • Convenient outfits are especially important when you need to run to the restroom.
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    Bring layers if it’s chilly. Since the weather might suddenly change up on you or you and your buddies might hit more wineries in the evening, come prepared. Stow your outerwear, like a fitted denim jacket or a jewel tone blazer, in your car or throw it on if you need to keep warm.[4]
    • A blazer's also great because it'll dress up any top right away.
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    Wear earthy tones, dark colors, or floral prints. Try not to court danger by wearing white—Murphy’s law might kick in, and you may get dirt or dust all over your outfit. Plus, if you or one of your friends gets a little too tipsy and spills wine on you, it’ll be way easier to blot it off of a dark shade or a busy pattern.[5]
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    Pull out your best statement prints. Make your wine tasting trip a fairy tale that’s worthy of dreamy IG posts. Since you may be surrounded by seemingly endless vineyards, lush trees, and even stone castles, dress for the occasion. Act like you’re about to waltz onto a photoshoot in your most eye-catching piece, like a striped maxi dress.[6]
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    Elevate jeans with a dressy top. While it’s totally acceptable to wear denim jeans or shorts, balance out these low-key bottoms with whimsical blouses. For example, wear a silk off-the-shoulder floral top with skinny jeans or a boho peasant blouse and a gold layered necklace with a pair of shorts. You’ll radiate care-free glamor right away.[7]
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    Stick with a small purse. Make sure your hands are free and avoid a clutch or a big bag that can get knocked around—it’ll be easier to laugh it up and tell stories to your friends while carrying a wine glass. Plus, you’ll probably have a lot of h'orderves and tiny desserts to look forward to.[8]
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    Keep your hair easy to manage. Help yourself get in the zone and truly savor all the glasses of wine. Instead of a high-maintenance hairstyle like a tight bun, go for a look that won’t require a ton of touch-ups. Try fun but simple beachy waves, an easy fishtail braid, or a high ponytail.[9]
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    Use chapstick instead of reapplying lipstick with each glass of wine. Keep your lips soft and supple in case you want to take a cutie selfie. Apply your favorite chapstick and slip it in your purse so it’s there whenever you need it. Not only will you avoid smeared lipstick, but you won’t leave any telltale marks on your wine glasses, either.
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    Skip perfume or strong fragrances. While it’s usually nice to put on a signature scent, any kind of perfume will only clash with the wine you’re drinking. Part of the experience is getting immersed in the fragrance of wine so you can pull out some essential aromas, like chocolatey or tart notes.[10]
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Section 2 of 6:

Spring Outfits

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    Maxi dress, sunglasses, purse, and heeled sandals. Throw on a maxi dress that really brings in spring with tropical prints, floral patterns, or fresh shades like mint green, baby blue, or mustard yellow. Make your outfit pop with fun oversized sunglasses, a woven purse, and neutral heeled sandals.[11]
    • If you wear a high-low maxi dress, match your manicure to your heeled sandals.
    • Add extra elegance and a "queenly" vibe by giving yourself semi permanent highlights.
    • For a prim and sweet look, try a maxi dress with flared sleeves.
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    Off the shoulder blouse, silk slacks, and slingback shoes. Tuck a light toned off the shoulder blouse, like one that’s white or light blue, into color-coordinated silk slacks, like a pair that’s olive green or beige. Then, add a fun twist with statement slingback shoes, like a zebra print pair. Finish off your look with a purse in a neutral shade.
    • If it’s really bright out, pop on cat eye sunnies for a Parisian flair.
    • For a dash of girliness, put on a dainty gold necklace.
    • Style your hair in loose waves to add romance to your sleek outfit.
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    Floral mini dress, straw hat, and ankle boots. Slip on any floral mini dress of your choice. Then, slide into color-coordinated ankle boots and pop on a straw hat. Use your small bag to make a statement—go for an envelope bag for old world elegance or a mini fashion backpack for fresh trendiness.[12]
    • For a femme fatale look, wear a black floral dress with red lips, a black felt hat, and black ankles boots.
    • For an ultra innocent vibe, pair a white floral dress with a pink fedora and round woven purse.
    • For a breezy ensemble, match a blue floral dress with a straw hat and beige ankle boots.
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    Long sleeve tie front blouse, maxi skirt, and strappy sandals. Choose a long sleeve tie front blouse in a fun and whimsical spring shade, like bright yellow or mint green. Then, complement it with a black and white striped maxi skirt. Complete the ensemble with strappy sandals in the same shade as your top and tassel earrings.[13]
    • To help your tassel earrings pop, style your hair in a high ponytail.
    • Wear light-colored tassel earrings so they’re not overpowering.
    • Put on a bold red lip to balance out a white and black maxi skirt.
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Section 3 of 6:

Summer Outfits

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    Flowy shirt, paperbag shorts, straw hat, and strappy sandals. Pull out any flowy shirt you like—one that’s light toned, dark toned, or patterned will work. Tuck it into a pair of color-coordinated paperbag shorts, then pop on a straw hat. Slide into some neutral strappy sandals and accessorize with tassel hoop earrings.[14]
    • For a fun and fresh ensemble, go monochrome with a light blue top and light blue paperbag shorts. Then, pair your outfit with white tassel hoop earrings, white strappy sandals, and a straw hat with a black brim.
    • For a more creative twist on this look, wear a jewel-toned top with black paperbag shorts. Pair these pieces with black wedge sandals and multi-colored tassel hoop earrings.
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    Embroidered peasant blouse, shorts, and beaded sandals. Go for a dark or light colored embroidered peasant blouse, then tuck it into a pair of high waisted denim shorts. Style your hair in beach waves, throw on a small straw hat, and slide into a pair of pretty beaded sandals.
    • Since a peasant blouse is a little busy, wear dark matte makeup so your beautiful face stands out.
    • Balance out the earthiness of ripped hem shorts with a fresh mani and pedi.
    • Swap out a straw hat and pin a flower in your hair to radiate goddess vibes.
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    Two-piece maxi skirt set, bangles, and ankle boots. Walk around like the princess of the vineyards with a dreamy two-piece maxi skirt set. Choose any light or jewel tone that reminds everyone of summer, like white, yellow, or pink. Help your ensemble pop with a set of color coordinated bangles. Finish off the look with a pair of ankle boots or dressy sandals.[15]
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    Tie front dress, tassel earrings, and slingback clogs. Choose a tie front dress in a summer tone like rose, or go for a fun pattern. Stripes, floral print, or a tropical design are all fun options. Put on some earrings and slide into a pair of neutral slingback clogs. Throw on a round woven purse and you’re ready to enjoy wine in the sunshine.[16]
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Section 4 of 6:

Fall Outfits

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    Form-fitting autumnal sweater, tweed skirt, and knee-high boots. Slide into a bodycon sweater in a lovely fall shade, like a chocolatey brown or a rust orange. Then, wiggle into a color-coordinated tweed skirt. Complete your ensemble with a pair of knee high boots in a neutral shade.[17]
    • Choose a bodycon sweater with an upscale material like cashmere.
    • For a richer color palette, try on knee-high boots in a dark brown shade.
    • Sling on a quilted purse in a neutral tone to play with textures.
    • Wear a small medallion necklace to draw attention to your figure.
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    Black top, black jeans, black ankle boots, and wine colored cardigan. Put together a drop dead gorgeous monochrome ‘fit with a black sleeveless top, black jeans, and black ankle boots. Then, pull it all together with a splash of color by throwing on a wine colored cardigan.
    • Add a rock star edge with a black felt hat and a black purse with silver studs.
    • Wear a dark smokey eye and a matte lip balm to accentuate the autumnal tones.
    • For a cool city girl vibe, wear a belt with a metal buckle.
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    Autumnal ruffle hem dress, gold medallion, and brown ankle boots. Slip into a ruffle hem belted dress in your fave fall shade, whether that’s copper or burnt orange. Add some pretty simplicity with a gold medallion necklace, then slide into brown ankle boots. Sling on a color-coordinated shoulder bag and wander the vineyards in style.[18]
    • For a mysterious vibe perfect for spooky season, try a black manicure.
    • To look like an IG influencer, get creative with colors and wear a white felt hat.
    • If you want to seem more upscale, wear a brown fashion monogram purse.
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    Beige sweater dress, fitted corduroy jacket, and white ankle boots. Shimmy into a form-fitted bodycon sweater dress in a shade like oatmeal or beige. Add some warmth to the look by slipping on a fitted corduroy jacket. As your finishing touch, throw in some modern glam with white patent leather ankle boots.
    • To make your ensemble ultra-feminine, slip on a brown leather purse and put on some gold-rimmed sunglasses.
    • Try a fashionably messy updo to lend some extra elegance to a sweater dress.
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Section 5 of 6:

Winter Outfits

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    White sweater, jeans, geometric cardigan, and boots. Toss on a fresh white bodycon sweater. Complement your top with skinny jeans. Add a pop of color with a warm and cozy geometric cardigan. Then, conjure up some sass with a pair of knee high boots.[19]
    • To add more texture to your outfit, accessorize it with a black quilted purse.
    • Conjure up some whimsy by layering dainty gold necklaces.
    • Wear some volumizing mascara or falsies to look ready for a winter photoshoot.
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    Colorful belted jumpsuit, ankle boots, and shawl. Step into a jumpsuit with a belt in the front and tie it into a bow for extra flair. Since a jumpsuit is a statement piece, choose a bold jewel tone, like emerald green, mustard yellow, or navy blue. Slip into ankle boots to keep your feet warm. Then, throw on a shawl and chain wallet to dazzle your friends with your powerful outfit.[20]
    • Skip jewelry since the whole ensemble is already really eye-catching.
    • Wear a chain wallet in a different jewel tone than the one for your jumpsuit.
    • Choose a shawl in a solid tone for understated elegance or with a fun pattern like paisley to look like a free spirit.
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    Long sleeve tiered dress, gold necklace, and slouchy boots. Slip into a long sleeve tiered dress in a winter shade, like deep purple or burgundy. Enchant your buddies at the winery by accessorizing with a dainty gold necklace and some fun slouchy boots.[21]
    • For a winter look at a beachfront winery, pair a blue or white dress with a sweater cardigan.
    • For a vibe that’s girly with an edge, wear a long sleeve white tiered dress and use hair chalk to add rose gold tips to your locks.
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    Knitted puff sleeve dress and tall suede boots. Choose a knitted puff sleeve dress in a bold color like white or black—a jewel tone like sapphire blue is totally fine, too. Add simple but elegant touches, like small gold hoop earrings and a gold charm necklace. Style your hair in a basic bun and slide into tall suede boots to look like absolute royalty.[22]
    • For a cool and sassy touch, pop on gold-rimmed oversized sunglasses.
    • If you want an ethereal vibe, get a mani with a neutral shade like a dusty rose matte.
    • For some extra mystique, pair a black knit puff sleeve dress with a jewel tone mani.
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Section 6 of 6:

Wedding Attire

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    Cut-out maxi dress and chunky heels. Choose any cut-out maxi dress that makes your heart sing—for example, go for a solid tone, a metallic shade, or a floral print. Slip into some color-coordinated chunky heels, sling a dark purse over your shoulder, and put on a dainty necklace to make the vineyard your runway.[23]
    • For a cool and chic vibe, wear a whole assortment of stacked rings with a floral cut-out maxi dress.
    • To look like a Bond girl taking a break to sip wine, pair a red cut-out maxi dress with gold chunky heels and a white wallet purse.
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    Satin midi dress and strappy heeled sandals. Slip into a satin midi dress in any shade of your choice (other than white). Coordinate this statement piece with a pair of color-coordinated metallic strappy heeled sandals. To draw attention to your shoulders and neckline, put your hair up and wear sparkling chandelier earrings.[24]
    • If you want to shine a little bit more, add a small metallic necklace to your ensemble.
    • Use hair chalk to achieve blond highlights that’ll play off your satin midi dress.
    • Try a French tip manicure for an ultra upscale look.
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    Asymmetrical shoulder dress and ankle strap heels. Wiggle into an asymmetrical shoulder dress to give off Grecian goddess vibes. Choose a color that feels regal to you, like gold or emerald green. Slip into neutral ankle strap heels and try a fun hairstyle like tousled waves. When you arrive, everyone will know the festivities are about to begin.[25]
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    Lace overlay dress and strappy mules. Choose any lace overlay dress other than a white one so you don’t upstage the bride. For example, try a fresh and feminine periwinkle dress or one that’s black to look like you’re part of the Roaring 20s. Slide into neutral strappy mules so you can toast wine and dance the night away.[26]
    • For a dash of uptown fashion, pair a pink lace overlay dress with beige strappy mules and a white wallet purse.
    • For a really decadent outfit, slide into a red lace overlay dress and white strappy mules. Play off your color palette with a French tip manicure.
    • For a vibrant and creative ensemble, wear a lace overlay dress in a jewel tone like emerald green and slip on a gold wallet purse.
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References

  1. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  2. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  3. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  4. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  5. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  6. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  7. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  8. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  9. ↑ https://www.winespectator.com/articles/what-to-wear-to-a-wine-event-47626
  1. ↑ https://www.winemag.com/2015/08/13/14-rules-for-visiting-a-tasting-room/
  2. ↑ https://chicpursuit.com/what-to-wear-to-winery/
  3. ↑ https://www.sparklesandshoes.com/2020/08/floral-mini-dress/
  4. ↑ https://brunettefromwallstreet.com/blouse-trends/
  5. ↑ https://www.whowhatwear.com/cute-shorts-outfits
  6. ↑ https://www.justthedesign.com/co-ord-outfits-the-two-piece-outfit-sets/
  7. ↑ https://tiaperciballi.com/navy-tie-neck-dress/
  8. ↑ https://www.idodeclaire.com/2021/10/tweed-mini-skirt.html
  9. ↑ https://affordablebyamanda.com/2019/08/loft-floral-hem-dress-workwear-look.html
  10. ↑ https://50isnotold.com/how-to-look-your-age-but-not-frumpy/#/
  11. ↑ http://www.ourlovelydeseret.com/jump-the-suit-floral-jumpsuit-summer-style/
  12. ↑ https://closetfulofclothes.com/how-to-wear-maxi-dresses-in-winter/
  13. ↑ https://www.countryandtownhouse.com/style/fashion/puff-sleeves/
  14. ↑ https://www.vogue.com/slideshow/cut-out-dress-trend
  15. ↑ https://www.elegantlydressedandstylish.com/turning-heads-linkupfall-trends-nyfw-potters-clay-satin-midi-dress-mango-look-2/
  16. ↑ https://katemiddletonstyle.org/item/jenny-packham-asymmetrical-dress-silver/
  17. ↑ https://katiesbliss.com/2014/04/lilly-pulitzer-lace-overlay-dress.html

About This Article

Cassandra Sethi
Written by:
Cassandra Sethi
Personal Stylist & Image Consultant
This article was written by Cassandra Sethi and by wikiHow staff writer, Madeleine Flamiano. Cassandra Sethi is a Personal Stylist, Image Consultant, and the Founder of Next Level Wardrobe, a luxury personal styling service for busy professionals. With over 20 years of fashion industry experience, Cassandra helps people transform their confidence by creating a work wardrobe they love to wear. Cassandra holds a BA in Fashion Merchandising from California State University, Long Beach, and a Postgraduate Certificate in Fashion Buying and Merchandising from the London College of Fashion. She created Soulcycle's retail business and was the Senior Buyer for 90+ Equinox gyms. Cassandra has been featured on New York’s PIX11 in an interview about how to achieve great work-from-home style as well as in Men's Health, Business of Fashion, and NYMag. This article has been viewed 4,472 times.
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Co-authors: 4
Updated: November 14, 2022
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