Have you ever had a winery trip planned and just stared at your closet, completely stumped? I know I have! You want that perfect blend of cute, comfortable, and practical.
Well, say no more. I’ve rounded up the absolute best outfit ideas that will have you feeling amazing from the first pour to the last.
1. White Blouse, Distressed Jeans, and Ankle Boots
I am always here for a look that mixes edgy with elegant, and this one is a total home run. Start with a breezy white blouse.
Its flowy shape and lightweight fabric have that casual elegance that feels so right for a day of sipping and strolling. So comfortable!
Then, bring in some cool-girl energy with black distressed jeans. The rips give the whole outfit a bit of an edge, kind of a nod to that rugged Americana style.
For footwear, beige ankle boots are the perfect choice. They create a nice contrast with the black denim and tie in with the whole neutral vibe.
And if you’re really feeling it, a wide-brimmed black hat adds a fun, Western-inspired twist to the whole look.
2. Orange Dress and Sandals
Is there anything better than a sunny day and a vibrant dress? This eye-catching orange number is just so perfect for warm weather.
The color totally mirrors the feeling of being out in the sunshine and vibrant surroundings.
I love that the shoes are a matching pair of orange sandals. The open-toed style is a must for keeping cool on those hotter days, and coordinating the color makes the whole look feel so intentional and put together.
This is definitely an outfit that embraces all the fun-in-the-sun vibes. So cheerful!
3. Oversized Plaid Coat, Turtleneck, and Boots
When the weather gets a little brisk, this is the kind of cozy-chic outfit I live for. It all starts with an oversized coat in a bold plaid print.
The roomy fit is perfect for layering, and the red and white pattern has such a retro feel. It totally gives off cozy cabin vibes and a little bit of holiday nostalgia.
A simple turtleneck underneath is a great choice for lightweight warmth, and it just peeks out from the collar.
To finish the look, some knee-high brown leather boots are a must. The rich brown shade goes so well with the red plaid.
I also love that they have a low block heel, which gives you a tiny bit of lift but is still super walkable. This is such a great winter-ready look that will keep you stylish and toasty all day.
4. White Lace Dress and Nude Sandals
This gorgeous white eyelet lace dress is giving me all the vintage charm feels. The thin spaghetti straps are great for showing off your shoulders, and the flared, tiered skirt creates the most dreamy movement when you walk.
The white lace has this intricate, elegant feel that almost gives off bridal vibes, but the casual fabric and length keep it relaxed enough for a daytime event.
For shoes, a pair of nude strappy sandals that wrap around the ankles are just perfect. Nude shoes are always a good idea because they make your legs look longer, especially with the dress hitting at mid-calf.
A chain-strap crossbody bag adds a little metallic shine and really polishes off the outfit. This whole look is all about laid-back sophistication.
5. Floral Print Dress and Black Boots
Here’s a fun way to show off your style! This floral print dress with its colorful flowers is such a great choice.
The floral pattern feels so right surrounded by all the lush vineyards. It’s the kind of skirt that would be so fun to twirl around in.
Then, you can add a little contrast to the prettiness of the dress with some matte black knee-high boots. I love how their edgy vibe balances out the super feminine floral print.
Plus, boots are always a practical choice for a long day of walking. Just add a white crossbody bag for a little pop of contrast, and you’re good to go.
6. White Sleeveless Tiered Dress
You can never go wrong with a light and breezy look, and this airy white sleeveless dress is such a classic. The tiered design hits just above the knees, and a simple white dress like this just screams summer.
It honestly never goes out of style! The tiered skirt sways so nicely when you walk, which is perfect for staying cool.
This minimalist dress is a great base that goes with pretty much anything. Paired with flat sandals, it’s super casual.
But you could totally dress it up with wedges or heels and some statement jewelry for a more elevated vibe.
If the temperature drops, just throw a denim jacket over the top. A versatile white dress like this is basically a blank canvas for you to get creative with accessories.
7. Burgundy Long Sleeve Dress and Boots
For those cooler days, a loose-fitting burgundy dress is such a cozy choice. The long sleeves are perfect, and the hemline ends just above the knees.
Burgundy is such a classic wine-inspired color, and it brings a really rich depth to the whole look.
The unstructured fit makes this dress incredibly comfortable, which is key for a day of walking and wine tasting. The long sleeves will also keep you warm if there’s a breeze.
As for shoes, some beige knee-high boots are a great way to make your legs look longer while giving you a little extra coverage. Their neutral color works really well with the bold burgundy of the dress.
This outfit is the perfect mix of stylish and practical for those transitional seasons.
8. Off-the-Shoulder Black Maxi Dress
Talk about timeless elegance! This black, off-the-shoulder dress is just stunning. It sweeps the ground in such a smooth, graceful way.
Black is one of those universally flattering colors that works on every complexion and always creates a streamlined silhouette.
The off-the-shoulder neckline adds a touch of romantic allure, which is really enhanced by the dress’s sweeping maxi length. You’ll feel so elegant as it sways in the breeze between tastings.
Because the dress is such a statement on its own, I’d go with minimal accessories. This lets the dress be the main event, as it should be!
9. White Button-Down Shirt, Matching Mini, and Pointed Heels
For a look that just radiates refinement and poise, you have to try this combo. It starts with an oversized, crisp white button-down shirt paired with a matching white mini dress.
Tying the oversized shirt is a great trick for adding some shape while still keeping it breathable on warm days. The matching white mini keeps the whole outfit looking so streamlined and crisp.
To elevate the look, add some pointed-toe heels with ankle straps. The pointed toe makes your legs look longer, and the studs and heels really dress up the more casual white pieces.
This is such an upscale yet comfortable look that definitely makes a style statement.
10. Ruffled Pink Dress and White Heels
I am so here for the romantic charm of this stylish pink dress. It features an off-the-shoulder ruffled overlay and a skirt that flows down to just below the knees.
The soft pink color is all about feminine prettiness, which is perfect for when you want to feel your best.
The skirt sways with every step, which adds such a nice fluid movement to the outfit. To complete the look, white open-toed heels are a timeless choice. They act as a neutral base that lets the pink dress really shine.
Plus, the heels help to elongate your legs and lift your posture. This whole outfit has such a playful sophistication that’s perfect for a day of winetasting.
11. Off-the-Shoulder Dress and White Sneakers
This is such a great way to beat the heat. This light green off-the-shoulder dress falls just above the knee, and the flirty neckline is perfect for keeping things breezy on hot days while showing a little bit of skin.
The light green color just evokes a sense of freshness and vibrancy.
For shoes, I love that this is paired with white sneakers. It keeps the whole look ultra casual, and their sporty vibe is a nice contrast to the feminine dress.
Plus, sneakers are a must for staying comfortable while walking from one winery to another.
An orange handbag adds such a cheerful pop of color and really ties the whole look together. This bright, lively outfit will definitely have you feeling as sunny as your surroundings.
12. Green Trench Coat and Leggings
Here’s how to stay polished and ready for any weather. A jungle green trench coat with a belt cinched at the waist is such a smart choice. The timeless silhouette of a trench coat always looks so stylish.
When you’re picking leggings, go for a dark color so the vibrant coat can really be the star of the show.
Leggings are great because they move with you, providing all the comfort you need as you walk between tasting rooms.
To complete the outfit, just add some ankle heels. This ensemble is such a beautiful blend of function and style.
13. Sleeveless Top, Skirt, and Light Brown Accessories
This look is both stylish and practical. It features a breezy white sleeveless top and a versatile brown skirt that hits mid-thigh. The white top really brightens up the outfit and is super breathable on hot days.
And bonus: you don’t have to worry about spills during an enthusiastic tasting!
The brown skirt is a great neutral foundation that goes perfectly with the white top.
For shoes, knee-high light brown boots make your legs look longer and have a chic, equestrian vibe. They also protect your calves if things get a little dusty.
A wide-brimmed light brown hat is the perfect finishing touch, adding a bit of glam while giving you some welcome shade.
The boots and hat match the brown skirt perfectly. This outfit really balances style and function.
14. Light Blue Maxi Dress and Sandals
You will definitely catch some glances in this light blue maxi dress. It has a cinched waist and a flowy skirt that goes down to the ankles.
The lightweight fabric is so breathable, and the light blue color makes me think of cloudless skies. You’ll feel like a Greek goddess in this ethereal dress.
Open-toed flat sandals help keep the outfit casual. Their minimal design really lets the ornate dress be the center of attention.
This breezy and beautiful outfit is an absolute winner for summer winery visits.
15. Pink Tiered Dress, Pointed Flats, and Clutch
If you want to stand out from the crowd, a lively tiered dress in a vibrant pink is the way to go. The bright pink color immediately catches your eye and feels so perfect for sipping on some rosé this season.
Pointed black flats are a great way to balance the look. Their sharp silhouette contrasts so well with the soft ruffles of the dress. The ankle straps give the shoes such an elegant, wrapped appearance.
For your essentials, an intricately embellished golden clutch is the perfect accessory. This whole outfit is so fun and feminine and just radiates confidence.
16. Leopard Print Dress and Ankle Boots
Time to unleash your wild side! This bold leopard print dress with long sleeves and a side slit is such a statement piece. The eye-catching leopard print really commands attention.
The deep V-neckline takes the wow factor up a notch, and it works so well with the daring print. I love that the long sleeves provide some balance by keeping you warm and cozy.
The side slit gives a little peek at your shoes, which are tan ankle boots. They perfectly complement the warm, earthy tones in the leopard print.
Their shorter style is great because it won’t weigh you down while you’re walking around. This fierce yet comfortable outfit will definitely announce your stylish arrival.
17. White Blouse, Skirt, and Ankle Boots
This is such a great way to balance casual and sophisticated pieces. The look pairs a textured, cropped white sweater with a sleek black ankle-length skirt.
The white cropped sweater gives off a sense of lightness with its color and easy drape.
Maxi skirts create such a beautiful, fluid movement as you walk. Ankle boots help to ground the look, and their shorter silhouette is a nice alternative to tall boots.
I’d pair this with a small black handbag that has an intricate pattern or some interesting hardware. The mix of contrasting textures and neutral colors really lets each piece stand out.
Final Thoughts
And there you have it! So many amazing looks to inspire your next trip to the vineyards.
The biggest takeaway? Don’t be afraid to mix and match pieces to fit the vibe of the day, whether it’s super laid-back or a little more glam.
Whether you’re channeling vintage vibes with lace details for a historic vineyard or going for a rustic feel with earthy tones, there are so many options.
An off-the-shoulder dress is perfect for a sunny day, while leather jackets and booties are great for those countryside views.
The most important thing is that you feel amazing in what you’re wearing. Confidence is always the best accessory, right?
With the right outfit, you’ll be ready to relax, sip, and enjoy the full experience. Before you know it, you’ll have a whole rotation of perfect wine tasting outfits.
Enjoy all the flavors and have a glass for me!
