Summer Wine Tasting Outfits That Are Elevated and Practical

I recently went on a little summer getaway to wine country, and boy it did not disappoint. I visited Napa Valley for the first time last winter, but I had never spent much time in Sonoma County. This trip offered me a stellar overview of the area, and honestly, every little bit of my trip felt special.

Summer in wine country is undoubtedly different to any other season, especially winter which was all I had experienced in the area prior to this trip. The summer temperatures are hot, there’s little to no breeze, and yet it can cool off quite a bit in the evening (which makes layering key.)

If you’re heading out on your own trip, I hope you find this as a good source of inspiration on what to wear wine tasting in the summer. Below, I’m sharing a handful of outfits I wore during my time sipping vino, exploring Healdsburg, indulging in dinner, and kicking back by the hotel pool. While these looks are specific to the warm weather season, they can all be altered to suit a cooler climate as well (just add more layers or swap out your shoes!)

Summer Wine Tasting Outfits

Travel Day Outfit

First things first, let’s talk about getting there. Travel days don’t mean you have to stick with basic black leggings and an oversized hoodie. In fact, I’m of the mindset that traveling is worth dressing up for, especially if you’re heading directly from the airport to some sort of social outing.

When I say “dressing up” I don’t mean that you have to sacrifice comfort. Slipping into a simple pair of jeans and a cozy sweater will do the trick. I tend to get chilly during flights, so reaching for warmer pieces is a must. I also had a morning flight and landed in San Francisco, which is generally a cooler and foggy city.

For an added layer, I threw this cropped trench coat on top. It’s chic, versatile, and lightweight enough for transitional seasons. It also came in handy with other outfits during my trip!

Dinner Outfit

This was one of my favorite looks from my trip, and it consistent of the perfect blend of fabrics for the warm weather during the day and cooler temps at night. I love that you can wear the slip dress on its own or with the sweater vest layered on top. Options are always a pro in my book, and this gave me the flexibility to wear this duo from day to night.

When heading to wine country in the summer, I highly suggest packing a variety of slip dresses. Tote along outerwear like a denim jacket or a cardigan for additional layering options.

Also, these under $100 sandals have been a major champion in my summer wardrobe lineup. They are so comfortable, they look high-end, and they’re an incredible price point.

Breakfast and Shopping Outfit

Let me tell you a little secret — I own this dress in multiple colors and prints, and it’s a piece I’d suggest every gal adds to her wardrobe. The linen fabric makes it lightweight and breezy for hot days while the simple silhouette ensures it’s versatile enough for everyday wear as well as for more special occasions. The chocolate brown color is also majorly trending at the moment (and will be a hit come fall, too.)

I slipped into this look for a little breakfast and shopping outing, but it would have worked equally as well for a wine tasting or dinner.

Also, I received a lot of questions about this straw hat. I purchased it from a boutique in Healdsburg (Bon Ton Studio), but I’m linking a similar find below! Not only is it a practical accessory but it provides a more “styled” feel to this outfit, which might have otherwise fallen flat.

Like I mentioned above, having ample layers with you in wine country is essential (yes, even in the heat of the summer!) If you plan to be out into the evenings, you’ll want to bring along something that will keep you cozy. Plus, restaurants, shops, and tasting rooms can crank their AC during the hot months, so it’s wise to have an option to keep you comfy if needed.

This linen blend bomber jacket is a more recent purchase of mine, and it was another pick that got good wear during my trip. It was easy to pack since it’s not too bulky and would even make for a nice layer to wear on the plane. I know I’ll be styling this on repeat this autumn!

Pool Day Outfit

While most of my time was spent indulging in wine and delicious bites, I was able to sneak in a bit of pool time at our hotel. The ability to kick back poolside is one of the major perks to traveling to wine country in the summer — and it truly offered the R&R I was looking for.

I packed this vibrantly printed one-piece for this trip. I’m a big fan of the bold pattern mixed with more neutral colors — the ideal combo in my opinion. It’s not shown here, but I also wore the matching sarong. These two picks would make for a cute beach vacation outfit as well!

Vineyard Visit Outfit

Not to toot my own horn but this outfit scored me lots of compliments, and it’s a duo that I plan to rewear as we inch into the transitional season. The linen striped top was practical for wear in the summer heat, and despite going for pants, I stayed cool enough thanks to their lightweight and breathable consistency.

I almost always pack some type of linen pants or trousers when I travel, regardless of where I’m going. They’re easy to toss in your suitcase since they don’t take up much room, and they’re a nice alternative to jeans. I haven’t been to wine country in the fall but I image these would be a great choice to bring along with you then as well!

Wine Tasting Outfit

Another highly coveted staple I bought this summer? This understated and classic linen dress. If you’re sensing a theme here, it’s that linen was a go-to. For your trip, I’d suggest incorporating a few linen picks that you can wear not only once but possibly a couple times. Even going for a maxi linen dress would be chic (and nice if you’re visiting toward the end of summer/into the fall.)

To add more dimension and visual interest to this outfit, I threw a striped cardigan over my shoulders. Even if you don’t intend to wear a layer, using this strategy will leave you with a more thoughtful look.

Dinner Outfit

Everything about this silk slip dress is special. For starters, I wore it during our anniversary trip to Italy, so it’s now associated with the best of memories.

Aside from the sentimental angle, it’s simply a gorgeous piece that’s both timeless and unique. The butter yellow color creates a warm pop of color while the lace detailing provides a more delicate touch. I forgot to snap a photo of my look in Sonoma but I pretty much styled this outfit this exact same way for a dinner in wine country.

The only swap I made was with my heels — I went with these gold pumps instead!

Travel Day Outfit

Ahhh the dreaded “travel back home” day. I don’t know that I would have ever been ready to leave wine country, but my love for the area just makes me eager to come back! For my venture back to Indianapolis, I wore this cashmere lounge set, which I actually bought during the Nordstrom Anniversary sale. From the first wear, I know this is going to be a new favorite of mine.

It’s ideal to travel in because it’s comfortable but also elevated. I added my cropped trench coat on top for an added dose of cozy and kept things streamlined on the bottom with a pair of ballet flats.

Which summer wine tasting outfit idea is your favorite? Let me know in the comment section below!