Cheryl Shops

This post could also be titled What NOT to wear in Pebble Beach, because—full disclosure—it was FREEZING when we took these photos, but such is life in Northern California in June. To back up a bit, I spent an awesome weekend at an AirBnB in Pebble Beach with a bunch of friends, and if you've never been there, it's one of the most beautiful places in California. (I know I say that about every place I go in California, but there's something really magical and special about Pebble Beach.) The trees are draped with this mystical-looking moss, the beaches have blindingly white sand, and the coastline can be rocky and rugged in some places, soft and lush in others. The challenge is that the weather can be all over the place—50 degrees and foggy one day, 75 and sunny the next. So the key to dressing for Pebble Beach weather can be summarized in one word: layers.


I have a rule for Northern California dressing, which is always bring a lightweight jacket. You've seen this J.Crew jacket here before (most recently in this post), and for good reason—it goes with nearly everything, and it's the perfect weight—not too light, not too heavy, but just right.

There's something so classic about a blue and white striped tee (last seen way back here)—this one is always in heavy rotation in my closet. Full, disclosure, however: you can see my cardigan peeking out in a few of these photos. It was so cold when we shot these that I had to add a third layer too!




This pink pleated mini (last seen here) has been getting a lot of love on my Instagram—plus it's currently on major sale at Bloomingdale's—so I wanted to feature it again, in a more casual outfit than last time. I like the mix of pale pink with a neutral (the army green jacket) and a deeper color—the blue in my top, necklace, and shoes—a general rule is to vary the tones, so you're not wearing all soft or all bold hues.


I've featured this Gigi New York bag several times on this blog—most recently here, as a clutch—and as I noted last time, it's one of my favorite bags to take when I travel, since it works for day as a crossbody and for night as clutch. There's also something a little unexpected about it being navy, rather than black.




When I was putting this look together in my mind, the stripes in my T-shirt were closer to the bright color of the stripes in my tee. Not quite, but I'm still happy with the pop of contrast that the shoes provide. As I mentioned the last time I wore these, they're not the easiest to build an outfit around—nor were they the wisest choice for the great outdoors—but wearing them makes me happy, so I make it work.


If you've been to Pebble Beach before, you might have noticed the Lone Cypress tree behind me in some of these photos—it's supposedly one of the most photographed trees in North America and over 250 years old! So I'll forgive it for upstaging me in these photos. ;)



OUTFIT DETAILS: J.Crew jacket (this season here: similar here) || Publish tee || BCBGMAXAZRIA skirt (on sale!) || Gigi New York bag || Sam Edelman shoes (also in black and blush here) || Stella & Dot necklace (sold out; similar here)