Cheryl Shops

One of my favorite parts of living in San Francisco is that it's so close to wine country. If you time it right, you can be in Sonoma County in under an hour, or a little longer for Napa County, but not by much. While wine tasting is obviously a big part of the experience, for me, the best parts is getting outside, breathing in some fresh country air, and enjoying the weather, which is usually 10–20 degrees warmer than in the city. If you follow me on Instagram, you know that I go to wine country quite a bit (I call my outings #SundayWineChurch), so I feel like I've perfected dressing for the nuances in weather. Here's what I recommend wearing in wine country in late spring. 

Target x Rachel Comey quilted cropped jacket (lots on eBay)

In the valleys where wine grows in California, the weather tends to be very cool in the evenings and very warm during the day, so if you're getting an early start, you probably want to bring a light jacket. (This relates to my #1 rule for San Francisco, which is: always bring a jacket.) Of course, chances are the rest of your outfit is pretty cute and so you want the right top layer for it, so as not to ruin your whole vibe. This very busy Target x Rachel Comey jacket was a little outside of my comfort zone when I bought it, but it has quickly become one of my favorites. It is surprisingly warm given how lightweight it is, and the slightly boxy cut reads a little eccentric Brooklyn architect, but I love how it keeps the look fun and doesn't cover up my dress. The jacket has long since sold out at Target, but there are a bunch for sale on eBay. It runs TTS—I'm in a small. 

Rhode Resort Ella Dress

Unless I'm going to wine country in the late fall or winter, I almost always wear a dress. It makes the trip feel a little more special, and when the weather is warmer—especially in the summer and early fall—I find a dress is the most comfortable thing to be in. You might recognize this Rhode Resort Ella dress from my birthday wishlist; I treated myself to it during Saks' friends and family sale a few months ago. I feel like every influencer owns this dress, and now I know why: it's super fun to wear. The fabric is a very lightweight woven cotton, which was a surprise (I was expecting more of a jersey T-shirt material), and there is a lot of it—steaming this dress takes quite awhile. It comes with a very thick braided belt, which you can use to adjust the fit to your liking. This dress is cut very generously, and I feel like it could fit a range of sizes and body types. I took my usual size small, and while it's definitely roomy, I think an extra-small would have been too short. 

3AM Forever chain-strap bag (here's a dupe) 

When it comes to wine country bags, there are two schools of thought: one is to bring a roomy tote bag to hold your jacket, a bottle of water, snacks, and so on. I am in the other one, which is carry a smaller shoulder bag so you are unencumbered while tasting wine. This wild little faux fur thing is a Bottega Veneta dupe that I bought after having a very strong brunch cocktail in Coronado Island; I can't remember the name of the shop, but thankfully Amazon has something that's almost exactly the same. Normally I wouldn't carry a pink bag with a pink dress, but they're different shades and textures, so somehow it all kind of works. 

Sarah Flint Perfect Block Sandal 30 (use code SARAHFLINT-BACHERYLSHOPS for $50 off)

When it comes to wine country shoes, leave the stilettos and kitten heels at home. Flats, wedges, or low block heels are the way to go, because even if your tastings are indoors, most wineries have some sort of gravel or dirt path to walk along, and you don't want to ruin your shoes or, worse, wipe out after your tasting. Like all of Sarah Flint's shoes, these sandals are comfy AF—they have a thick layer of padding in the sole, and in spite of being on the thinner side, the instep strap is actually really comfy. Plus, the low block heel is nice and sturdy, even while walking through the garden with a glass of sauv blanc in your hand. I'm a fan of the gold color too—I feel like these are going to be my go-to neutral yet slightly fancy summer sandals. They run TTS—I'm in my usual 39 (I wear an 8.5 US). Don't forget to use my code, SARAHFLINT-BACHERYLSHOPS for $50 off!

OUTFIT DETAILS: Target x Rachel Comey quilted cropped jacket (lots on eBay) | Rhode Resort Ella Dress | 3AM Forever chain-strap bag (here's a dupe) | Sarah Flint Perfect Block Sandal 30 (c/o) | Feisedy sunglasses