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Modern And Chic Fall Winery Looks For Your Next Tasting Session


Modern And Chic Fall Winery Looks For Your Next Tasting Session - Blog Banner

Headed to your favorite winery this fall? As the vineyards transform into a picturesque tapestry of autumnal colors, there’s no better time to savor the exquisite taste of fine wines while indulging in the beauty of the season. A day of wine tasting is not just an opportunity to explore new flavors but also a chance to showcase your personal style against the backdrop of rolling vineyards and sun-kissed grapevines.

In this blog post, we’re here to help you curate the perfect blend of modern and chic outfits that harmonize seamlessly with the cozy and sophisticated ambiance of a winery.

Whether you’re a wine connoisseur or a casual enthusiast, these fall-inspired ensembles will ensure you look as captivating as the scenery around you during your next tasting session. Join us as we uncork fashion-forward ideas for an unforgettable winery visit.

What to Wear to a Winery in the Fall

One of the best parts of going to a winery is getting to choose your outfit (and the wine, of course!).

Fall brings with it a cool breeze that is perfect for thicker fabrics and modest, fashionable outfits.

Read on for some modern ideas on what to wear to your next winery–and make sure to tailor each outfit to reflect your taste.

Modern and Chic Fall Winery Looks

There are so many ways to arrive in style to a tasting session–which can make choosing a look an overwhelming process.

Below is the proverbial cheat sheet to modern and chic looks you’ve been waiting for–so you’ll no longer have to wonder about what to wear to a winery in the fall.

Jeans and a Flowy Top

For a casual yet classy outfit, opt for a pair of jeans and a flowy top. Then, complete the look with fall-friendly ankle boots.

Wondering where to start? Citizens of Humanity has the perfect straight leg jeans for this occasion that’s relaxed. Pair it with this puff sleeve shirt from Revolve to set the mood for a fun-filled and laid-back evening.

Since this is a full outfit, you can pair it with white sandals and a cute bag to create a modern boho chic winery outfit.

Fall Winery Outfit with Jeans

But for you boot lovers, you can also grab a pair of your favorite neutral-toned ankle boots, preferably white to feel cozy and look chic in your jeans outfit at the winery.

Long Skirt and Button Down Shirt

Look effortlessly chic with a maxi skirt, a button-down shirt and some mules.

A maxi skirt such as the Mare Mare Poplin has just the right amount of flow and comfort for a seamless evening out at a winery. Pair it with the striped silk shirt for the right amount of stripe to go with the toned-down red maxi.

This fit wouldn’t be complete without the casual vibes brought by the bestseller Linnie Bit mules from Sam Edelman, which are known for their combination of comfort and style.

Fall Winery Outfit with Long skirt

Slip Skirt and Blazer

Slip skirts are lightweight and perfect for summer weather. But you can also wear it in fall by adding a wool blazer and belt it around the waist will look elevated and perfect to wear to wine tasting. 

You can easily accessorize this outfit with link chain necklace and hoop earrings

And complete the outfit with loafer mules. This modern elevated wine tasting look will turn heads for sure.

Fall Winery Outfit with Slip skirt

Sweater Dress And Tall Boots

Embrace fall weather with a chic sweater dress cinched with a statement belt and knee-high boots.

Head to none other than Sezane for their electric blue Freja sweater dress. Then, cinch this beauty with their Artemis belt in yellow for the perfect statement piece. 

You’ll need some knee-highs to complete this look, and Sam Edelman’s Clarem suede tall boots in a camel-colored tone help to create a fun and chic outfit that both wows and feels comfortable.

Faux Leather Skirt With Sweater And Blazer

Faux leather skirts are perfect for an elevated wine tasting outfit. But instead of using flowy tops that will create a bohemian look, wear a black short sleeve sweater or turtleneck. 

This way your outfit looks modern and smart. This is not the only way to wear the faux leather skirt. Checkout some more more faux leather skirt outfits.

Of course, you’ll need heels that feel comfortable to walk in as you tour the winery and sip fine wine. Nisolo’s everyday ankle booties are chic enough to complete this outfit, while still keeping comfort in mind.

Wrap Dress With Structured Flats

A wrap dress and a pair of ballet flats guarantee that you’ll stay comfortable during your entire tasting session. It’s a simple, sleek and modern outfit without any fuss.

Slip into a dark tone wrap dress and opt for the structured flats by in beige to create a classy yet fun and comfortable wine tasting outfit.

This outfit looks current yet chic with the wrap details of the dress.

Shirt Dress And Knee High Boots

Fashion-forward and a bit couture, a shirt dress and some knee-highs can quickly be elevated by going all leather. 

To achieve this, wear this beautiful Sezane shirt dress that has puff sleeve and built in belt. 

Then, pair it with Maryana Lo crocodile-embossed leather boots from Schutz. The textured crocodile pattern will complement the smooth faux leather from your shirt dress.

It’s like a look straight off the runway and into your winery of choice.

You can simply swap the fabric belt with a chic white leather belt or a brown leather belt to completely imbibe the fall wine tasting look.

Pencil Skirt with Shirt And Boots

Pencil skirts have been revised this year and they are the perfect elevated alternative to slip skirts. They look structured and are warm and cozy for cooler weather.

Wear this beautiful pencil skirt from Maeve which has the fall olive tone. Part it with a classic stripe shirt with sleeves rolled up for a casual yet sophisticated outfit.

Now for the fun part. You can either wear a neutral tone boots with this outfit, or go for brown tall boots. Either way you will create a chic as well as updated outfit you can rock at the next wine tasting.

Wrap Top With Wide Leg Pants and Heels

Alternatively, you could tone it down with an elegant wrap top, wide leg pants and subtle black heels. 

And why not go all monochromatic while you are at it. Now it does not have to be red. But I had to share this beautiful wide leg red pants from & Other stories paired with this red wrap shirt that looks so chic.

Since this outfit is all covered up and looks so stylish and sophisticated, you don’t need to make it to heavy by wearing boots. Instead go for strappy sandals that will look elegant and  make you look even more tall. And add your favorite bag for a fun wine tasting session where you just look cool.

Silk Blouse With Leather Pants And Sandals

Mix textures like a pro with the right silk blouse, leather pants and strappy heels.

For a feminine and sophisticated touch, opt for this beautiful pink Mauve silk like top from Your Favorite Daughter. This is a bodysuit by the way, so you don’t have to worry about the tuck not staying in place.

Contrast the softness of this top with Agolde wide leg faux leather pants.

Lastly, slip into a pair of black open-toe heeled sandals from Coach that are versatile and comfortable for a look that draws the eye in with ease.

Statement Sleeve Dress + Wedge Pumps

You don’t need to just wear a bohemian dress to a wine tasting. The dress can also be tasteful and elegant. Just have a little bit of drama with some drama in the sleeves.

That is exactly what this beautiful modern printed wrap style dress with sheer puff sleeve dress from Shona Joy is doing. 

It has looks flirty, elegant and sophisticated. And comes in the fall perfect shade as well.

You can pick open toe sandals with or go for mule heels that are  close toe so your feet stays warm.

Off Shoulder Top With Leather Pants and Boots

When the weather has cooled down, but you still want to bare some skin, an off-the-shoulder knit sweater can work wonders–especially when paired with faux leather pants and ankle boots.

But I know off shoulder sweaters and tops always look outdated. Instead let’s go for this classy Reformation silk off shoulder top in black which also comes in other pretty shades. Then, combine it with a pair of pleated wide leg faux leather pants from Frankie shop.

Add in a black belt to elevate this outfit further. And complete your look with the Mikki booties from Schutz in black to balance the black top.

Crushed Printed Shirt With Blue Jeans And Sandals

Ready to stand out from the crowd while sipping wine and enjoying a nice view? 

This printed crushed shirt has pleats around your cleavage that looks so fun and because of the jersey fabric, they are comfortable to wear too. This gorgeous green print shirt is from Boden and also comes in black

Pair it with your favorite wide leg blue jeans to balance the proportion. A great way to rewear your everyday jeans for a special occasion.

The blazer is optional, but this way you stay cozy and look chic. 

I like slingback pumps, but you can also go for your favorite sandals. 

Mixed Media Dress with Sweater Jacket

Picked up a beautiful printed dress that you think you can only wear to work or for summer, think again. You can absolutely wear it with some fun layering to wine tasting. 

This beautiful mixed printed dress from Ann Taylor is giving us all the Italian lady vibe. It’s fun, flirty and still classy and sophisticated. 

You can add a third layer with a similar burgundy sweater jacket and keep your heels and you have yourself a modern and sophisticated wine tasting outfit. 

Short Sleeve Sweater And Printed Pants

This is one of my favorite outfits, so was saving it for the last. Printed pants have made a huge comeback and I am all for it. It looks fun preppy and perfect bottoms for wine tasting. 

And this Maeve Printed pants are versatile pair too. You can wear it with tshirt or simple solid colored top for summer weather. And for a fall wine tasting event pick a short sleeve sweater

This way you can layer up without getting too hot. The awesome part is that since these pants are cropped in length, you can either pick your favorite flats or add mule heels.

For more on fall styling, please read:


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About Suchi

A Techie turned Fashion blogger, I have been in your shoes. I have gone from looking like I was trying to fit into my teen clothes, to now a stylist and blogger known to be classy and elevated style. I can help you look your best without spending too much time, effort and money into your wardrobe. 

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