Fall Winery Outfits

Blue Mini Dress For Fall

One of the top Fall activities that many of us like to partake in are winery visits. Fall just becomes the perfect time to visit a winery because it’s not too hot, and even if it gets cold, you can still find a cute, chic outfit to wear to keep you warm as you sip wine by the fireside or roam the vineyard. When considering your fall winery outfits, some people tend to think that they have to give up the luxe look that they want to create and instead just go for comfy and functional, but that isn’t the case.

When it comes to creating wine tasting outfits, there are a variety of things that you want to consider. Maybe you’re thinking about going to a winery in your local area where the wine is available but it isn’t the same as to what you would find in wine country. Or maybe you’re doing a wine tasting in a place like Napa Valley, where the wine is plentiful and some of the places fluctuate from casual to more upscale. In that case, you may be asking yourself what is the deal wine tasting outfit.

In this post, I’m sharing some great wine tasting outfit ideas as well as aspects to consider when putting together your Fall winery outfits. Whether you’re thinking about wearing a mini dress or a maxi dress or maybe you thinking about skinny jeans and going country casual while going on your wine tour, this post is going to give you the baseline on how to take in the wine tasting dress code and create the perfect outfit.

Blue Mini Dress For Fall



When it comes to wearing dresses in the Fall as a part of a fall winery outfit, many of us automatically go to sweater dresses and long-sleeved dresses. And don’t get me wrong, that’s a great place to start and that’s probably the first place I start as well, but it doesn’t mean that you completely ignore that short-sleeved dresses that you already have in your closet as well as the ones that you still see stores selling.

If you’re considering wearing a dress of any length for your perfect wine tasting, one thing that you absolutely need is either a light jacket or a coat depending on which season you are planning to visit the winery. And with visiting a winery, if you’re choosing not to wear jeans, is to make sure that you style boots that match the length of the style of dress that you are wearing. For example, if you’re going with a midi dress, go with booties, but if you’re going with a mini dress, then knee high boots or over the knee boots are what you want to go with.

Stores and boutiques sell short-sleeved dresses throughout the year because, during Fall and Winter, you can layer on top of a dress as well as underneath for you wine tasting event. Layering is the optimal style tip for not only being able to wear a warm weather dress during the colder months, but it also the style tip that will get you to extend your closet and make those splurge worthy outfits worth the credit card swipe.

Style Tip: Don’t think of layering as just putting a jacket or cardigan underneath a dress, think of layering also as getting a neutral top to put underneath the dress and make it look as if the dress was long-sleeved the entire time – essentially extending your wardrobe.


There are a variety of different Fall looks that you can put together for your wine tasting outfit. And there are a number of different aesthetics of wineries that you may want to match your look to. For example, maybe you’re heading to a winery out in the country that is a little laid back, so you want to elect with going with wine country casual instead of sophisticated and upscale, or maybe it’s vice versa and you’re going with a little more of an upscale, evening date night look especially if you’re not going to the actual vineyard but for a classy dinner at the winery where they might have those members only wine bottles that you want to taste, but you’re not quite sure you’re ready to spend all of that money on just yet.

I’ve rounded up a few fall winery outfit ideas to give you a baseline of outfits that you can add to your closet and then build off of for your next wine tasting outing. The great thing about these outfits is that you can mix and match a lot of the pieces to create all new looks. And is you want to grab one of those items, just click on the piece in the photo and it’ll take you to where you can purchase it.


Fall Winery Shop

Aritzia Long Sleeved Dress


When considering what to wear for your fall wine tasting, there are some aspects that you want to take into account as you plan your outfit. With the Fall being a season where the weather can be quite unpredictable with temperatures fluctuating throughout the day, and with wineries handling tastings in different ways, here are some things that you may want to consider:

  • Is the weather going to change throughout the day. If you look at the weather report and it says that the temperature is set to rise or it’s going to be a windy day, you may want to put together a more layered outfit. With the layering, you can shed or add pieces as needed.
  • What is the “vibe” of the winery? While most wineries are casual, there are some wineries that have a more upscale feel. So for the latter, you may not want to wear an outfit that is jeans and sneakers, but instead, wear a dress with a pair of booties to make it a upscale but still comfortable look.
  • What type of activities will you be doing at the winery? You may be going on a wine tasting that also includes a tour of the vineyards or one that has some yard games for you to play. In that case, make sure that you wear comfortable shoes that you don’t mind getting dirty.
  • What was the weather like the day before? This will effect the type of shoes that you wear. You may not want to wear heels if you’re walking along the grass or in any dirt and it had rained the day before.
Fall Blue Mini Dress
Fall Dresses

Fall Winery Outfits BY THE MONTHS


Though September still has a lot of the summer feel, many people start visiting wineries for wine tastings in September when the weather is slightly warmer. In that case, as you are planning your Fall winery outfits for September, I would advise going with a lot more lightweight looks. Satin is a great fabric to wear during the transitioning weather and it’s a hot trend, so create your outfit with a satin dress or a satin top with pants.


October is probably the biggest months for wine tastings, so you may even be looking at tips in this post specifically for putting together a Fall winery outfit for October. October is a great month for visiting wineries because it’s not too cold, but it’s not hot and it’s a great time to break out those comfy sweaters and jackets. For this month, I would recommend mock neck sweaters paired with pants and booties or a midi dress with a lightweight jacket.


November gets a little cooler, but it is still a great time to visit a winery right before Thanksgiving. For your Fall winery outfits for November, I would recommend something a little more snug and layers that will keep you warm if you are out in the evenings which comes sooner because of daylight savings time. At this time in the year, it’s time to break out a comfortable wool coat for the evening and cute sweater dresses. There are great sweater dresses that also have corset look embedded into it so that you can show off the figure under the coat while also staying super comfy.

Long Sleeved Blue Dress
Must Have Fall Dresses
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