Cheryl Shops

If it seems like I'm traveling a lot lately, well, I am. I have always loved to travel, and the pandemic pretty much brought that to a screeching halt, so now that life has (pretty much) gone back to normal, I'm making up for lost time. My day job is also 100% remote, which means I can work from anywhere, so when Sean has a business trip in an interesting location, I tag along. And lucky him, he had a work conference in Honolulu last week! Flights from San Francisco to Honolulu were very reasonable and I had a free place to stay (thanks, Sean's work!), so it was kind of a no-brainer. (Although, to be fair, my workdays started at 6:30 a.m., which was an adjustment to say the least.) I mean, who's going to turn down a trip to Hawaii? (Not me!) Here's what I wore.

In case you missed last week’s post, we recently spent a week on the Big Island of Hawaii and it was pretty much amazing. We had booked the trip months ago, soon after I started a new job that was a bit more stressful than I'd anticipated, and to be honest, the thought of a relaxing week at the beach got me through some pretty rough weeks. Of course, a week before we were due to leave, the governor of Hawaii issued a plea for tourists to stay home until later in the fall due to rising Covid rates and full hospitals; after some thorough investigation and a pledge to spend as much time outdoors as possible, we decided to go anyway. (We were far from alone, by the way.) Here’s what we did on our blissful trip to the Big Island.

If you've subscribed to my newsletter, you know that I'd been looking forward to our Hawaii trip for a long time. You also probably know that I've been on a pre-vacay spending spree. For one, it had been a year and a half since we'd taken a proper vacation, and over three years since we'd gone somewhere tropical. I also think, deep down, I miss not spending money on dress-up clothes for specific things and I had a lot of pent-up money to burn. I tried to shop (somewhat) responsibly, but may have gone a weee bit overboard. At least—fingers crossed—I'll be able to wear everything on our long-postponed trip to Europe next summer. But in the meantime, here's what I wore on our Big Island vacation. 

Proving that I've never been one to follow trends, here I am posting about what I wore on vacation while everyone else is bundling up in sweaters, boots, and coats. But hopefully some of you have a winter getaway coming up, and thus this post will come in handy! I just spent a week in Hawaii—four days in Maui, four in Kauai—and it was pure bliss. I'd never been there before and was blown away by how exotic and magical it was—especially Kauai, which felt like a cross between Jurassic Park and South Pacific (both of which were filmed there). For one, there are the sunsets.

Gathering to watch the sunset was a nightly occurrence at our hotel, and a fun one at that, especially with a mai tai or glass of wine from the bar. Another vacation ritual I enjoy is wearing a dress every night to dinner—after being in a bikini and flip-flops all day, it just feels nice to get dressed up and go out.


A little white dress is the little black dress's warm-weather cousin, and this off-the-shoulder style is pretty much universally flattering. I love the straight shape of this one too—it camouflages the four pounds I gained on vacation (yes, those mai tais add up)—AND it has pockets!




I also love to wear gold jewelry on vacation, especially once I have a good tan going. I like to keep it delicate, though—when I'm in warm weather, I don't want to overwhelm myself with big, clunky jewelry. I also tend to get really lazy and not take off my necklaces while I'm at the beach (hey, that makes it even easier to get dressed for dinner!).


Not counting my flip-flops, I brought five pairs of shoes on this trip and ended up wearing two of them—one being these slip-ons that I featured in this post. Of course, sometimes I barely even wore them, like when my photographer had me frolic on the beach for these shots (it was worth it, of course—the lighting was way better). I mean...


OUTFIT DETAILS: Banana Republic dress (similar here on sale) || Quay Australia Odin sunglasses || Stella & Dot abundance necklace and engravable disc necklace || Catbird ring, X ring, tiny CZ ring || Chan Luu beaded bracelet, Stella & Dot open cuff and rectangle cuff || Stella & Dot hammered wire hoops || Sam & Libby slides (similar here on sale)