Fall Wine Tasting Outfits That Are Cute and Practical

fall wine tasting outfits

A trip to wine country is never a bad idea, but if you have flexibility and can be picky about when you go, there’s no better time than the fall. Autumn marks peak harvest season, meaning the vineyards are at their best (and they’re ready to show off for you!)

While hotels and experiences will certainly be more pricey during the fall months, I personally think the scenery and overall feel during this time of year makes it worth the splurge. Whether you’re planning a girls trip or a couples getaway, wine country has so much to offer (and yes, there’s more than just a good glass of chardonnay to enjoy!)

I might be biased because I live in Sonoma County, but we truly have so many incredible restaurants, bars, and small shops that are fun to explore. I know that Napa County also has a ton to offer — so take this as your sign to start mapping out your itinerary for a visit.

With all that being said, I know that deciding what to wear in wine country can be quite tricky. Throw in the fact that the weather can be moody in the fall and things only get more challenging. You might need something that you’ll be cool in during the day as well as something you can layer on as it gets chillier at night. Plus, there’s always the chance that you see sunny and comfortable temps one day, then cool and crisp elements the next (that’s coastal living for ya!)

To help you prep for your own trip, I’m sharing a handful of fall wine tasting outfits below. Each of these looks caters to a different style, yet all are practical enough for all-day wear!

Fall Wine Tasting Outfits

Denim Dress and Stiletto Boots

There’s just something about a denim dress that screams fall to me. This one has such a unique shape and I adore the slight puff sleeve detailing. I’d pair it with some brown suede boots, but if you want something more comfortable, you could always swap them out for white sneakers (Adidas Sambas would look cute!) Add some sunglasses, gold earrings, and a handbag to pull everything together.

Fall Wine Tasting Outfits Denim Dress and Stiletto Boots

Jeans and a Cardigan

If you need a cute wine tasting outfit that’s suitable for cooler temperatures, consider this your new go-to. The striped cardigan offers a preppy and polished look while the jeans provide a classic and comfortable base layer. Ballet flats are always a good choice in the fall, and they have the added perk of keeping your toes covered (aka warm!)

Fall Wine Tasting Outfits Jeans and a Cardigan

Sweater Dress and Western Boots

If you’ve been following me for a while now (or reading the blog for some time) then you might know I have a deep rooted love for a good pair of cowboy boots. They happen to be one of the most practical shoe choices for a wine tasting excursion, especially if you plan to walk through the vineyards at all. I have a full post dedicated to cowboy boot styling, but for a fall winery look, I’d keep things simple with a sweater dress and some accessories. Sweater dresses are a fool-proof choice for fall wine country wear because they keep you warm on top but offer some breathing room below. 

Fall Wine Tasting Outfits Sweater Dress and Western Boots

Cardigan and a Denim Skirt

I have always been a fan of maxi skirts, and the denim maxi skirt trend is no exception. Again, denim is very much on-theme for the fall season, so lean into that by wearing it in a less expected way (a skirt, dress, or even as a chambray top!) Pair one with a button up cardigan and a tank or tube top underneath, then finish with western boots, loafers, or mules.

Fall Wine Tasting Outfits Leather Jacket and Jeans

Leather Jacket and Jeans

For a moodier outfit idea, opt for jeans, a dark colored top, and a leather jacket. This would be the ideal choice to wear from day to night/for grabbing dinner after vineyard hopping. Straight leg jeans are typically my favorite style, but wide leg jeans or a cropped pair of denim would also look cute. As far as shoes go, ankle booties are another practical option. You could go with something with a small heel or something on the flatter side — it just depends on what you’re most comfortable in!

Fall Wine Tasting Outfits Leather Jacket and Jeans
Erika's Signature

Hi! I’m Erika and I live in Sonoma County with my high school sweetheart and two kids. Follow along to find home inspiration, delicious recipes, and the inside scoop on all things wine country.

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