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If you’ve ever planned a trip with me, you’ll know that I refuse to step foot on a cruise and yearn to walk 20,000 steps a day. My ideal vacation typically consists of exploring a new city and reserving any sitting for the occasional espresso at a sidewalk café. It may come as a surprise, therefore, that when my boyfriend’s mom and sisters suggested a girls’ trip to a remote resort in Costa Rica, I couldn’t buy a plane ticket fast enough. Maybe I was inspired by The White Lotus; most definitely, I was in need of some major R&R.
While the respite was appealing in theory, lounging for even half a week was somewhat of a foreign concept to me and called for some fresh outfits to help me get in the right mindset. What would the most carefree version of myself wear in the most ideal weather? The answer to this question was: effortless styles + a bit more color than I usually go for.
By framing my resort-bound self as a character of sorts, I was able to embrace the temporary lifestyle shift—perhaps with a little too much success. Let me tell you: The 36-hour flight delay on my way home was a rude awakening after luxuriating in daily massages, morning yoga, and a cornucopia of freshly picked produce (I tried five fruits I’d never even heard of!).
Below, see four of the looks I wore when I wasn’t reclining in either a swimsuit or a spa robe.
Upon Arrival
After checking in, we wanted to get the lay of the land then head straight to the resort restaurant for dinner. The sun had already set, so the view would have to wait until morning. In its place, I let my outfit set the scene. Nothing says summer vacation like crisp white jeans, an olive-adorned tank, and a sky-blue cardigan suited for a gentle evening breeze. If you’re a fan of our Milo jean, you should check out the Abby, which is made from the same stretchy yet structured fabric but looks more like a cropped chino pant thanks to the tab closure. Shout-out to my friend Noelle, who gave out these actually useful bags (similar) on her bachelorette trip.
Breakfast + Sunbathing

This past winter in NYC felt especially long, so I was more than ready to soak up some rays the next morning post breakfast. I end up at a beach or pool only a handful of times per year, so I can’t justify owning a true cover-up. Instead, I rely on lightweight pieces to achieve the same effect. Here, I’m wearing an Andie bikini underneath a satin skort (similar) and M.M.’s Kenya T-shirt, a new silhouette that features a flattering scoop neck. Havaianas and a raffia bucket hat really summer-ify the look.
Being rainy season, the current weather pattern was clear in the morning followed by showers in the afternoon. Travel tip: This means rates are cheaper this time of year, plus you can experience sunny and cozy vibes each day. It’s the best of both worlds!
A Day at the Spa
The following day, I decided to book a massage after lunch. Of course, it didn’t really matter what I wore; all I needed was something effortless I could toss on for the short walk to the spa. I reached for the Kylan top and Adina shorts, since both of these pieces are nice and loose—perfect for allowing my skin to soak up all the lovely oils applied during my treatment. This look also felt put-together enough to reunite with everyone in one of the resort’s shared spaces without changing first.
Farewell Dinner
For our last hurrah, I wanted something slightly dressed up, and this new style, called the Cira, was just the thing. On the one hand, its shirt-dress silhouette reads relaxed, and on the other, its ikat-like pattern feels special enough for a nice dinner. You could dress it up with something like a metallic heel, but my favorite Ancient Greek sandals felt more appropriate for this setting.
Traveling for business rather than pleasure? Here’s how to pack: