Fall Fashion: 5 Anthropologie Dresses to Wear to a Winery this Season

Anthropologie The Somerset Maxi Dress: Chiffon Edition, Western Double-Buckle Belt,
Shop the Dress | Belt | Boots all ℅ Anthropologie | Similar Hat

Fall is one of my favorite times to go wine tasting. For starters, it’s when wineries are celebrating the harvest season.

During the harvest season, winemakers are one step closer to making their vintages a reality. There are a lot of highs and lows in the winemaking industry — frost can kill crops early on in the season, too much rain can dramatically alter the flavor profile, and other forces of nature can prove to be challenging for vintners. If you see a winemaker in the month of October, they may or may not need a hug (or a glass of vino!) depending on how well the harvest went.

Oh, and also, the vines also look spectacular this time of year. If you get a vineyard tour, you might be able to see some nearly-ripe grapes on the vines or enjoy the lush vine foliage. 

Temperature-wise, fall is also a great time to head to a winery. Summers can get too hot and humid at most U.S. wineries, and winters might be too cold. Don’t get me wrong, I love a good cozy winter wine-tasting day, but wineries often have much more outdoor seating available than indoor seating, making it a little less than ideal to go during colder months. In the fall, most likely, you’ll be able to comfortably sit outside, enjoy the weather, and even have a small picnic outside. 

All in all: fall is the best time to plan a winery visit. If you’re headed wine tasting soon, or if you’ve become inspired to go winery hopping in the coming weeks, here are five Anthropologie dresses to wear to a winery this season.

Temecula Olive Oil Company, Anthropologie The Somerset Maxi Dress

Temecula Olive Oil Company, Outstanding in the Field Dinner
Scar of the Sea Wines

Anthropologie Dresses to Wear to a Winery this Season

5 Anthropologie Dresses to Wear to a Winery this Season


The Somerset Maxi Dress: Chiffon Edition

Last week, Anthropologie hosted a beautiful dinner in Temecula (AKA SoCal wine country) in partnership with Outstanding in the Field, benefitting No Kid Hungry, and they kindly dressed the attendees of the event. I opted for their Somerset Maxi Dress in Chiffon, which was an absolute stunner! Their Somerset Dress is one of their top-rated products, and for good reason: it’s incredibly comfortable, flattering, and versatile!

I own a Somerset Dress in cotton, but the chiffon fabric of this dress is super dreamy and can be dressed up or down pretty easily. This could easily transition from the weekend to a winery to even a wedding! If you’re in between sizes, I would size down — I’m wearing a medium.

By Anthropologie One-Shoulder Mini Sweater Dress

I love a good sweater dress moment at a winery. You’re bound to spend a reasonable amount of time outdoors while wine-tasting, so you might as well stay warm and chic!

This sweater dress is high on my wishlist this season. It’s a timeless design you’ll want to reach for yearly. Sweater dresses tend to show almost every lump and bump, but this tie-waist detail is super flattering and will look fabulous throughout your wine-tasting adventures!

The Marais Printed Chiffon Maxi Dress

I rented this dress from Nuuly for my upcoming trip to Walla Walla, and I cannot wait to frolic in a vineyard in this little number! I love a flowy dress for wine tasting for comfort — my stomach does tend to bloat a little bit throughout a day of wine, cheese, and snacks, so having a bit of extra space in the waist area is always welcome.

Also, pro-tip: you can find a good amount of Anthro new arrivals on Nuuly for rent. I sort by “new arrivals” when picking items, and most of the pieces I rent are brand new with tags. If you enjoy a piece you’re renting; you can buy it at a discount!

The Somerset Maxi Dress

As I mentioned above, the Somerset Dress is always a great idea. If you’re not into prints this fall, the OG cotton version of the dress comes in several solid, neutral colors.

Pilcro Tiered Corduroy Dress

This dress is also in my latest Nuuly shipment, and I can’t wait to style it for wine tasting in Washington. I’ll rock a mini dress or skirt if I have a winery reservation and am guaranteed a seat. However, if you’re walking into a winery, sometimes, that winery only will have lawn seating available, making a long dress a little more practical.

We’re all set with reservations for next week’s trip, so I’m opting to show a little leg! I love the texture of this mini: ruffles and corduroy seem like a dream.

What’s your favorite thing to wear to a winery? Let me know in the comments below!

Photos by Tom McGovern

Leave a Comment


  1. Christine wrote:

    I think the dress you’re wearing is my favorite, but that one-shoulder dress is stunning too! And fall seriously is the best (and most beautiful) time to go wine tasting.

    Posted 10.24.22 Reply