Cheryl Shops

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. 

Old Navy Gingham dress

You saw this one back in June but it was kind of covered up, so here it is in all its bare-armed glory. This was actually a perfect beach-day dress: it's easy to slip on and off, it's nice and breezy, and the fabric is lightweight enough to dry quickly if it gets wet. (I've discovered that I basically need to bring one swimsuit coverup for every swimsuit, which I did not do on this trip, sadly.) Best part: it's on major sale now, and it has most sizes still available online. It runs large (I'm in a very roomy size small), so take that into consideration! 

OUTFIT DETAILS: Old Navy dress | Quay Australia sunglasses (similar here) | Birkenstock Arizona EVA sandals

American Eagle tennis skirt

We had planned to do a day trip to Hilo to see a bunch of waterfalls and the botanical garden; I had it in my head that I needed something sporty to wear, so I decided to try a skort for the first time ever. Let me just say, I am a convert! I loved how short and flirty the skirt was, but the fact that there are built-in bike shorts underneath means you don't have to worry about a wardrobe malfunction. Granted, this pose was one of the sportiest things I did all day (and I DO NOT recommend lying on a tree like this BTW, because I got attacked by bugs while doing it) but I look forward to wearing it on more occasions. I'm in a medium but probably would have been ok in a small, and if they bring it back in white, I'm totally getting another one. 

Do NOT try this pose unless you like bug bites!

OUTFIT DETAILS: Cabi top (c/o) | Offline by American Eagle tennis skirt | Birkenstock Arizona big buckle sandals (similar here) | Amazon sunglasses 

Target dress 

This was a last-minute purchase after I saw it on The Stripe. I have had much success with Target dresses this summer, and since this one had rave reviews (and a very palatable price tag), I figured I couldn't go wrong. Which was right! The dress is nicely body-skimming, and the elastic neckline can be worn up or off the shoulder (I chose the former because I hate strapless bras). It also has pockets, and I know we all love those. I was super comfy in this one, and I thought it looked lovely with my lei! It runs true to size, if a little big (I'm in a small), and comes in a bunch of different colors if white isn't your thing. 

OUTFIT DETAILS: Target dress | Hermès Oasis sandals | Amazon bag 

Devotion Twins dress

I've been obsessed with this one since Rachel wore the pink version in the last episode of The White Lotus (which I highly recommend binging if you haven't already), and clearly I'm not alone, because I've been seeing it in different colors all over my Instagram feed. This dress is cut very generously (I'm in a small) yet feels super chic—I got a compliment on it from the manager of the restaurant where we had dinner (more on that to come next week). The fabric is gauzy and breathable; I was perfectly temperate in this one too. Even better, it's something I can get away with wearing for a few more months (maybe even with boots) here in California. 

OUTFIT DETAILS: Devotion Twins dress | Dolce Vita Pally sandals

Greek Archaic Kori dress

And while we're on the topic of obscure European designers, I discovered this mouthful of a brand from Atlantic Pacific, and in the vein of Devotion Twins, Greek Archaic Kori makes very loose-fitting yet glamorous resort-y dresses that would look amazing having dinner in St. Tropez. A lot of their styles are better suited to smaller busts, so I went with this caftan-style one and I absolutely love it. They run rather large—I'm in a small (which was the smallest size available)—but not being able to see your food baby-belly after a week of eating and drinking to your heart's content is priceless, if you ask me. Again, I think this one will look fabulous with a maxi-cardigan and some ankle boots back here in San Francisco, but I can't wait to break it out next summer too. 

OUTFIT DETAILS: Greek Archaic Kori dress | Amazon bag | Dolce Vita Pally sandals

Please come back next week for my Big Island travel diary!