This post could also be titled “how to wear a sundress in fall.” As I’ve noted in the last few posts, fall in the Bay Area is one of the most beautiful, temperate times of year, and most visitors are surprised by how warm it is. Wine country—Sonoma and Napa counties especially—tends to be much warmer in the summer, but by fall, it’s just right, with highs in the upper 70s. It’s the perfect weather for a sundress…but as with weather year-round in the Bay Area, layers are key. I recently went up to Sonoma and Napa for the day, and here’s what I wore. If you’ve been reading Cheryl Shops for awhile, you might recognize this sundress as the one I wore in Bora Bora on my birthday trip. It’s now among my favorite dresses, and while I don’t get the opportunity to wear it a lot in San Francisco, I jump at the chance whenever I can, and it’s one of my go-tos for wine country. I love this dress because it looks like I’m wearing a cropped top with a high-waisted skirt, and the cutout detail is high enough to be flattering—in other words, it’s not at the pudgy part of my tummy. I wear a strapless bra with it because of the skinny spaghetti straps, but it’s super comfy otherwise, and I think the bias cut of the skirt is really flattering. Most importantly, it has pockets. I’m in a size medium for reference. I wore a lightweight black cardigan with this dress, thinking I’d remove it eventually when it got warmer, but that never quite happened, which is again why layers are important in wine country. A black cardigan is not the sexiest of things in one’s wardrobe, but it’s definitely practical, and since I wanted to stick to a truly neutral palette, it was the most logical choice. Mine is ancient, and by Lutz and Patmos, which is a brand that’s no longer in existence, but I’ve linked a similar style below. I’ve managed to not include my A.P.C. bag in the last two outfit posts, so obviously I was itching to wear it again. (In case you were wondering, I last wore it here.) That, and it’s my go-to weekend bag. I’ve said it before, and I’ll say it again: the size is just perfect, and I love the clean lines of the shape. I am also not one for glaringly obvious designer logos, so I love how understated the branding is. Speaking of other investments that I wear all the time, these Golden Goose sneakers are one of my current favorites as well. I’m usually more of a sandals person for wine country, but I wanted to go for a little more casual flavor with the dress, and I think they worked really well—these sneakers just go with everything. The best part is that they have a tiny hidden wedge that gives you just a little extra height, which helps with a dress. We shot these photos at Frog’s Leap, which is hands down my favorite winery in Napa Valley. I’m a member (or Frog Fellow, as they call it), and not only are their wines delicious, everyone who works there is incredibly friendly. Napa can sometimes have a reputation as being snooty, and Frog’s Leap is the complete opposite. Their property is absolutely gorgeous, too—we shot this post there last year. If you go—and you should—tell them I sent you! OUTFIT DETAILS: Bardot dress (on major sale) | Lutz & Patmos cardigan (similar here) | A.P.C. Sac demi-lune | Golden Goose superstar sneakers | Miansai screw cuff