Cheryl Shops

It goes without saying, but date night is usually my favorite night of the week. It almost always involves eating and drinking—two of my favorite things to do, and with one of my favorite people who also happens to be my very talented photographer—but the best date nights involve an element of novelty (really, it's true). On Saturday night, we went to see a play downtown, which was something that we hadn't done together, and even though the play was, um, one that we wouldn't recommend, it was still fun. Also fun: dressing up for date night. Planning a cute outfit and taking the time to dress up reminds me of when we were first dating, and at the risk of sounding cheesy, keeps the magic alive.

I'm a skirt girl, and always have been. Skirts are my go-to for date nights, but really, you should wear what you feel most comfortable in. It's all about highlighting the parts you feel best about—in my case, my legs. This particular skirt is by IRO, one of my favorite brands, and in spite of being white, it's pretty versatile. The phrase "universally flattering" always gives me pause, but an A-line shape like this is as close as you can get.

I'm also a heels girl, although mine are getting lower and chunkier as I age. This pair is sadly sold out—they're last-season Zara—but since the color is so crazy, I wear them with pretty much any random thing. In this case, they pick up the green in my necklace, which is also a little kooky.

The denim jacket and striped tee keep everything a bit more casual—and this being San Francisco, my number-one rule is never go anywhere without a light jacket. And, really, you can't go wrong with a classic denim jacket.



A good thing about getting older is that you can get away with statement accessories. Mirrored pink sunglasses? Sure! Huge mixed-media pendants? Why not! Do you, especially on a date.

I figured you were tired of seeing my bamboo bag by now, but this is one of my other weekend favorites. It's by Baggu, a San Francisco–based brand, and it holds a lot more than you'd think, thanks to some excellent pocket placement on the inside. I also love how soft the leather is, and that the strap is adjustable, so you can make it a crossbody too.


Back to date-night novelty, this park is exactly two blocks south of my apartment, and in spite of having lived there for three years now, this was the first time I'd ever been inside. (Since it's between my two cross-streets, it's on a particular block that I tend not to walk or drive down.) It's tiny and lovely and a little bit magic...just as date nights should be.


OUTFIT DETAILS: Vintage Gap jacket (similar here) || Publish striped tee || IRO skirt || Baggu circle bag || Stella & Dot York necklace || Zara shoes (sold out; similar here) || Quay Australia After Hours sunglasses (on sale!)