Cheryl Shops

Spotify's year-in-review posts came out last week, so you know what that means: time for the year-end wrap ups! I'm changing things up a bit this time; it's always hard to pick a favorite outfit of the year, so I thought I'd do something different and pick 10. This was actually harder to do than I expected; turns out I liked a lot of what I featured here (although I did have some duds, TBH). Still, it's funny to see some trends emerge: I still love neutrals, but I did try a little (soft) color here and there, and clearly I have some favorite accessories! In no particular order, here are my 10 favorite outfits of 2021—tell me your favorites in the comments below!

One of my favorite things about San Francisco is that you can get out of it quickly. After living in New York for years—where trains, buses, and even boats were required to take you mere miles away—I love that you can drive for 30 minutes and be in a completely different climate, which is pretty much necessary in August, when the city is constantly blanketed in fog (we call it Fogust). If you follow me on Instagram (and you should!) you know that I make frequent weekend trips to wine country; in less than an hour, I can be outside in the sun with a glass of rosé in my hand, and that is just perfection.

Over my four (!!!) years living here, I've gotten my wine country outfit down to a science. It involves the following:
1. A cute dress
2. A light jacket or sweater to keep you warm on the drive out of the city
3. A hat and sunglasses (must shield one's pale office-dwelling skin from the sun)
4. Low-heeled sandals for rocky and/or hilly terrain; bonus if they slip off for picnics


I'm wearing several of my favorite pieces of the moment. This sweater (sadly sold out!) is from Modern Citizen—a store so great, keep your eyes peeled for an upcoming post on them—and I've been wearing it nonstop. I love this dress because you can eat (or drink) as much as you want, and it's loose enough that you can't tell; it also has a really flattering hemline that's lower in back and not scandalously short in front.


As for the bag, I impulse-bought it a few weeks ago, and I don't think I've ever received more compliments on a purse, especially from men. It's really lightweight; I got the small size because the large felt a bit too large, like I was carrying a picnic basket.


Nearly every design magazine has covered them recently, but Scribe is the first winery I joined as a member, and I hate to refer anyone else there since it's always a madhouse, but it's one of the most magical places in Sonoma (it's where I conceived #sundaywinechurch) and their wines are delicious. I also recommend Larson Family Winery—it's a completely different experience, but their wines are tasty and reasonable, everyone who works there is incredibly friendly, and it's a great place to hang out for a few hours or all day.


OUTFIT DETAILS: Sole Society Panama Hat || Modern Citizen Ofelia sweater (sold out, sadly!) || Topshop T-shirt dress || Cult Gaia Ark bag || Raen Durante sunglasses || Madewell Greer sandals (sold out; similar here) || Rachel Zoe tassel bracelet (similar here) || Hermes Clic H bracelet || HappyWay Jewelry X-ring



Right down the road from Scribe is Domaine Carneros, which is where I like to go when I want to feel fancy. A wise woman taught me, too, that a proper way to start a day in wine country is with bubbles. Also, I'd like to note that temperatures in Napa reached 107 degrees on the day these photos were taken; I was wearing a denim jacket that I shed by 10 a.m. because it was already that hot (and yes, we like to start drinking that early). And when it's hot, we drink rosé.



This dress, sadly, is from last year. I bought it in Nice, France, from the most typically chic French woman you can imagine. It's incredibly lightweight and comfy, but chic too, and I always feel like I'm on vacation when I wear it.



There are a gazillion amazing restaurants in Napa, but our latest find is The Charter Oak, which had catered the fancy party I was at last weekend. It's by the same team behind The Restaurant at Meadowood, which has three Michelin stars (and like five dollar signs), but it's much more casual and the perfect stopping point for a midday refueling. Also, it has this very Instagram-friendly spiral staircase.


OUTFIT DETAILS: Etoile Isabel Marant dress (similar here)  || Raen Durante sunglasses || Cult Gaia Ark bag || Minnetonka Savona Sandals || Rachel Zoe tassel bracelet (similar here) || Hermes Clic H bracelet || Stella & Dot arc pendant, Signet ring || Chanel scarf (similar here)

What to wear to what? Concours d'Elegance is a week-long vintage car show in Pebble Beach, California—stick with me, ladies—and while the main event involves the man in your life drooling over a $20 million Ferrari 250 GTO, I agreed to go for the people-watching and the parties. The former runs the gamut from middle-aged men in windbreakers collecting sponsor swag to Botoxed trophy wives looking bored while their husbands make seven-figure bids on trophy cars. As for parties, I can only imagine what the high end of the spectrum is like, because we somehow ended up in the Carmel Highlands at the Cadillac House and for a couple hours, I got to pretend I was in an episode of Big Little Lies, minus the domestic abuse.



We took in the views, we lounged by the pool, we ate (free) lunch from the Charter Oak in Napa—which was so good, we're going there for brunch next weekend—and then I discovered the Jason Wu pop-up in the library. It's not as totally random as it sounds, as Cadillac's Escala comes with a set of Jason Wu luggage, but since the bags were largely being ignored by the (majority male) party attendees, I decided to borrow one for a few shots because a) they're simply gorgeous, b) they were much nicer than the one I was carrying that day, and c) when an opportunity like this presents itself, you seize it. Literally.


As for the rest of my outfit, this dress is an oldie but a goodie—it's breathable, it's flattering, and it looks great with or without a belt (I love a little status symbol in my accessories, particularly when I'm trying to blend in with people who have too much disposable income). The sunglasses are my new favorite pair, and the sandals are one of the most comfortable pairs I own, which is important when you're walking 14,000 steps, as I did.



OUTFIT DETAILS: Gap shirt dress (similar here) || Gucci belt || Jason Wu Mini Saddle Bag || Sam Edelman Trina sandals || Quay Australia After Hours sunglasses || Stella & Dot Trevally necklace, abundance necklace, pavé cuff, open wave cuff, signet ring, X-ring


This is the house, by the way—it's on sale for $10 million, in case you have a little extra change left over from the car auction.