napa valley spring wine tasting

Spring Wine Tasting Outfits That Will Elevate Your Experience

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It’s finally spring! A season that not only brings along with it new blooms, but also refreshes our wardrobe from the winter layers we might have gotten a little too used to. This time of year is the perfect excuse to start planning some winery outfit ideas. After all, is there a more perfect way to celebrate the season than with a relaxing day spent at your local winery or in Napa Valley, sipping on some of your favorite wines? 

When it comes to figuring out your closet for this occasion, there’s no need to worry – I’ve got you covered with plenty of classic, timeless outfit ideas that are perfect for a variety of springtime wine tastings. Whether you’re enjoying outdoor wine tastings with friends, a romantic anniversary wine tour, or a special event in an exclusive tasting room, your fashion game will be just as amazing as your Chardonnay. 


How to Pick the Best Spring Wine Tasting Outfit for You

Before we jump straight into this style guide for picture-perfect wine tasting attire, I’ve got to mention some of the important things to consider when choosing your different outfits. Things like location, weather, and occasion play crucial roles in determining what the best outfit choice is going to be.

After all, spring can look drastically different depending on which part of the country – or the world – you find yourself in during the season. (In the Midwest, spring basically feels like summer after our dreary winter, so there’s that.)

In general, vineyards call for a blend of comfort, style, and adaptability. After all, navigating through rows of grapevines or standing on grassy terrain is always more fun when you’re not struggling! Keep your specific location, weather, and occasion in mind as you peruse these outfit ideas.

Let’s get into it, shall we?

1. linen midi dress + v-neck cardigan + clutch + Mary Jane flat + hoop earrings 

wine tasting spring outfit

dress | cardigan | clutch | flats | earrings 

For a breezy, comfortable outfit that brings a pop of color, this first look is a great option. Featuring a simple, feminine silhouette, this dress falls beautifully on the body, making for a flattering fit on the chest area and a flowing ever-so-slightly outwards towards the bottom.

In general, different midi dresses make for great wine tasting outfit ideas – easy to wear and style for whatever the occasion and dress code, this piece is just the right design to enjoy a wine tasting tour in. When browsing to find other options, opt for a breathable fabric to help you tackle the (almost) summer heat. 

For places that have warmer weather during the spring, this outfit will be sure to keep you cool while still allowing your style to shine. As the sun begins to go down and the wind starts to pick up, layer this classic, off-white light sweater on top of your dress or tied over your shoulder. Not only does this piece add a layer of warmth to your look, but it also infuses your outfit with a chic and polished touch. 

Accessories are essential for completing an outfit, and this bag proves it. This woven foldover clutch brings the perfect spring and summer feel to this ensemble,  balancing the luxurious feel of the linen fabric and the cotton cardigan with its texture.

For shoes, these Mary Jane style flats keep your look delicate and super feminine without detracting from the main pieces of the look (and, of course, are super easy to walk in!).

Finish off this look with a simple, dainty pair of hoop earrings. 

2. wool pant + one-shoulder top + flats + skinny belt + clutch + hoop earrings

wine tasting spring outfit

pants | top | flats | belt | clutch | earrings

A special date or friend event at a vineyard would be the perfect opportunity to bring out this one-shoulder look. Elegant, simple, and comfortable, this outfit will make you look like you took a lot more time to get dressed than you really did. 

This ribbed top starts off this look with an immediately chic feel, elevating a simple look into something instantly more elegant and special. 

Pair your top with Italian wool pants, bringing the perfect fabric contrast to the outfit. For those who find themselves in warmer weather during your tour, a pair of linen pants can also be a good idea!

A brown handwoven clutch and a buckle skinny belt complement each other beautifully in bringing an accent to this neutral color palette, while also working to bring visual interest and structure to the final look.

Comfortable shoes are a must for your next wine tasting experience, but that doesn’t mean there aren’t some great, chic options available. For this look, go for these chic slingback style flats that feature a pointed toe and a gorgeous beige shade. An elegant closed-toe shoe makes for both a stylish and practical look that you definitely won’t regret. Throw on a pair of your favorite small hoop earrings for a delicate final detail.

3. linen top + pleated midi skirt + mule + crossbody bag + watch + scarf

wine tasting spring outfit

top | skirt | shoes | bag | watch | square

For a comfortable look that doesn’t slack on sophistication, this skirt and blouse combo takes the prize. It’s no secret that we love to lean towards flowy pieces in the spring. While it can look incredibly chic to go with pieces that are opposite in their fit (for example, skinny jeans and a flowy blouse), it can be fun to consider other ways of adding visual interest to the look. 

In this case, this look begins with a beautiful white pleated skirt. Sure, white and lighter hues may be a riskier choice for a wine tasting, but it doesn’t mean you have to avoid these colors completely! Take extra caution and if you’re not confident in your no-spill abilities, then copy the formula of this look and look for these pieces in darker colors.

But there’s just something special about this skirt! Featuring beautiful movement and an a-line silhouette, this skirt pairs beautifully with this linen scoop-neck top. Similar in overall look, these pieces complement each other well and can be worn both tucked in or not. 

For that special touch that you’ve been waiting for, add a silk scarf or a neckerchief to your look. By adding a gorgeous pattern and unexpected color to your look, this piece elevates your look and wins you some serious style points in the process. 

Matching your bag and your shoes is a technique as old as time – and yet it still works every time! While this definitely isn’t a strict rule, matching elements such as color or texture is a great way to bring both balance and a more cohesive feel to your look as a whole. That being said, opt for this classic mule and this small, structured crossbody for beautiful touches of brown and cream accents. 

As a final special element, opt for this beautiful and delicate gold-toned watch. Need extra warmth? Spring is the perfect time to throw on a denim jacket. A jean jacket can add a nice contrast to this chic look, blending casual and chic effortlessly.

4. oversized shirt + wide-leg jean + Mary Jane flat + clutch + watch + hoop earrings 

wine tasting spring outfit

shirt | jeans | flats | clutch | watch | earrings

Trade in your trench coat for a slightly bolder take on another tried-and-true closet staple with this dark blue striped button-down. With white stripes and an oversized fit, this shirt can be worn and styled in endless different ways throughout the spring – it could even become your vineyard uniform for the season! 

On the bottoms, pair your shirt with these wide-leg cropped jeans, perfect for keeping things breathable while still keeping you comfortable to walk and explore throughout the day.

Brown and blue work beautifully together, as seen by this gorgeous finished look. Both the woven clutch and the classic Mary Jane flats give the look its true style flair, while gold accessories like a bracelet watch and oval earrings polish it off! 

5. oversized poplin dress + woven mule + tote bag + flower stud earrings

wine tasting spring outfit

dress | mules | bag | earrings 

If you find that you tend to lean more towards dresses when thinking of the ideal winery outfits, then this look might just prove you right. In a navy blue color, this oversized poplin dress takes inspiration from the classic shirtdress for its silhouette. 

In a chic and crisp cotton poplin fabric, this piece also features dropped shoulders and wide sleeves, as well as a collar, front buttons, and a belted waist. Details like these – and side seam pockets! – make this style an exceptional choice for your day at the vineyard.

Match the oversized proportions of your dress with a large carryall bag that complements the look seamlessly while also keeping all of your essential items safe and looking stylish. 

For shoes, these woven mules will keep you comfortably on your feet as you explore your surroundings, while also adding some summery texture to the outfit and complementing your handbag at the same time. 

For a final delicate touch, add these gorgeous white flower stud earrings. This accessory softens the look ever so subtly, making for an altogether balanced and elegant ensemble. 

6. linen-cotton top + wide-leg jean + ballet flat + tote bag + dome earrings 

wine tasting spring outfit

top | jeans | flats | bag | earrings

This next outfit is a great choice for a more casual day at the vineyard when you still want to aim for an elegant and chic look while also keeping things simple. 

Begin with these wide-leg cropped blue jeans; designed specifically for an hourglass shape, these jeans provide plenty of support while also making room for your legs to breathe. Subtle raw hems make for a subtle distressed touch that works well with the other pieces in this look. 

On top, opt for this linen cotton shirt that encapsulates what it means to be relaxed. Comfortable and breathable design, as well as a luxurious-looking fabric, make this cute top the ideal choice for a day of wine tasting.

A relaxed fit is truly what defines this style, allowing you to be totally comfortable all day long. A v-neck detail and elbow sleeves give this shirt a sophisticated feel for the perfect look. 

This straw tote bag is a great choice of accessory, lending your outfit a touch of spring and summer just like that. Matching beautifully with the other black pieces in this look, this bag is able to bring all of the elements together while still adding its own unique texture to the ensemble. 

For shoes, this occasion might be the perfect opportunity to give these mesh ballet flats a go. Having recently gained popularity amongst fashion enthusiasts everywhere, this style gives this outfit combination a modern edge (and comfort for an all-day affair!). 

For a final touch, add these chunky dome earrings to add some more texture and variety to your look. 

7. linen-blend maxi dress + slide sandal + slouchy bag + bracelet + earrings

wine tasting spring outfit

dress | sandals | bag | bracelet | earrings 

I love maxi dresses for many reasons, but having a low-effort look on hand is definitely up there on my list.

This gorgeous linen-blend maxi can work well for a bunch of different occasions at the vineyard and can be totally transformed through some quick styling decisions. 

Made from a beautiful flowy fabric blend, this dress has no waist definition and features both an a-line fit and a crew neck detail. Perfect for staying cool during hot days, this fan-favorite dress also includes side pockets (did I hear 10 extra points?).

For an effortless and always elegant look, accessorize your dress with these heeled slide sandals. Not only do they give you a little height boost, but these shoes also work to bring in some accent colors and warm-weather textures into your look in an understated manner. 

Match your small slouchy bag to the brown shades of your shoe – a small detail that instantly creates an amazing look with just a few closet staples. Accessorize with some dainty drop earrings and a gold cuff for a polished final result! 

8. lady jacket + wide-leg jeans + ankle boot + shoulder bag + flower stud earrings + scarf 

wine tasting spring outfit

jacket | jeans | shoes | bag | earrings | neckerchief 

Lady jackets have undoubtedly earned their spot as a spring staple in my book, and this occasion is yet another perfect opportunity to break out this best-selling piece for your wine-tasting date.

Perfect for wearing on its own, this cute sweater features a shorter length and a more relaxed fit. If you’d like more coverage overall, consider sizing up. With front patch pockets and gold-toned button details, this more structured sweater jacket blends two traditional styles into an easy, versatile, and elegant piece. 

Pair your lady jacket with these wide-leg cropped jeans, perfect for showing off your shoe of choice while also ensuring you stay comfortable and mobile during the day. Raw-hem detailing gives a casual and effortless feel to the entire look, balancing well with the more structured elements of the outfit. 

For shoes, the Glove Boot is perfect for those who plan on staying on their feet without compromising on some high heels at the same time – after all, comfort is always going to be your best bet. Opt for this matching shoulder bag for a perfect accessory that once again works to bring the whole look together. 

Whether you want to wear it on yourself or on your bag, this beautiful neckerchief scarf adds a refreshing spring feel to this entire ensemble, integrating a subtle, delicate, and beautiful pattern into this look delicately and unexpectedly. Complement this piece by adding these statement flower stud earrings as the icing on the cake.  

Want to know how to effortlessly mix elegant and casual style? I have a free cheat sheet for you (and more) that you can access here!

Spring Wine Tasting Outfits: Embracing Elegance at the Vineyard

Dressing for a special occasion like a wine tasting should be an event of its own; a time to decompress, get creative, and pick the pieces that will make you feel like your best self!

The wide range of options available to you – from breezy linen dresses to chic one-shoulder tops, and casual blue jeans – offers a great starting point for your style journey. Not only will these looks keep you comfortable, but they’ll also make you look as amazing as you deserve to feel as you sip on some delicious wines.

These carefully curated looks not only ensure comfort and ease as you navigate through beautiful landscapes, but they also encapsulate the beauty and fresh feel of the spring season.

From flowy linen dresses that can catch the spring breeze to some more sophisticated layers that add just the right amount of warmth to your look, each ensemble is thoughtfully assembled to keep your style and your wine tasting experience in mind.  

Do you have a warm-weather vacation that you’re planning for? We’ve got outfits for that too. Up Next: 10 Stylish Beach Vacation Outfits to Pack for Your Next Trip


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.