#12 Packing diaries: resort packing
Balancing beachwear with city sensibilities - packing for the tropics when flowy dresses aren't your thing
Resortwear is pretty much the opposite of my natural state—and personal style inclinations. So, dressing for beach-y or tropical destinations has always been a little tricky. At the end of the day, I feel most like myself in a great pair of jeans, a tee, and a slouchy knit or blazer. Dressing for city life (specifically in fall or spring) is my happy place.
That said, I’ve always loved browsing aspirational beachwear edits. Letting my mind escape to those warm, breezy scenes is fun—even if I don’t quite picture myself in most of the outfits. I joke that you’ll find me in a dress maybe once a year, and honestly, it’s not far from the truth. It would make packing a lot easier if I could just slip into a flowy sundress and feel like myself, but that’s not the case. I’m slowly accepting that—and shifting how I approach packing for these kinds of trips. I’m curious: does your style change when you travel somewhere totally different from your usual environment?
For a while, I tried to convince myself I could be that girl—bought a bunch of Ulla Johnson, imagining I’d somehow transform into someone who felt natural in ruffles and feminine floral prints. Spoiler: I didn’t. I eventually consigned all of it through The RealReal. The one exception has been a printed silk slip dress from Khaite that I picked up several seasons ago. It works because of its simplicity and clean lines—it’s just easy. Throw-on-and-go.
For my recent trip to the Dominican Republic (mostly work, with a bit of pleasure), I wanted to be more intentional. Instead of buying resortwear that only works on vacation, I looked for pieces that could flex for city life too. In the past, I’ve made the mistake of buying overly specific items that end up collecting dust back home. I haven’t quite perfected my resortwear formula, but here are a few key pieces I brought on this trip—along with how I styled them with existing favorites from my closet. (*Affiliate links below.)
The Row Estelle Raffia Tote / This was the biggest new purchase. I’d realized I had a gap in my wardrobe when it came to airy, summery bags. And if I’m going to buy a new bag, I want it to be a lasting classic—and this one feels like it. I remember when it first launched, it was on my radar, but I never pulled the trigger. Then I saw Neelam Ahooja mention it again recently, rewatched her review, and into my cart it fell. After one trip, I’m really happy with it. It’s lightweight, smooshy, easy to pack, and I can already see tons of ways I’ll use it in the coming months. (It’s mostly sold out in this color “espresso” at the moment, but they do come in and out of stock. There’s also one here for a small premium.)
Matteau Relaxed Shorts / Super easy pull-on shorts, just a step up in formality from boxers. I love this particular shade of blue—it reminds me of the sea.
Jude Flip-Flop Sandals / I discovered this brand through Sydney Engelhart and thought they’d be perfect for the trip and upcoming summer plans. I love the minimalist design, but wow—these need some breaking in. A few other sandal brands I’ve considered: A. Emery, St. Agni, and Emme Parsons (these look so soft that they need no break-in period!).
Le17Septembre Asymmetric Top / An endlessly versatile piece that works both in the tropics and the city. I didn’t have time to steam everything when I arrived, and after a few hours of wearing this top, all the wrinkles disappeared. Maybe it was just the humidity but either way, great win.
Made in Mada Raffia Phone Bag / A beautiful little crossbody for just the essentials. I picked it up at one of my favorite local boutiques—Vestige in Fishtown. (Their curation is so good it’s dangerous.)
Leigh Miller Silver Cuff / Not a specific purchase for this trip, but a recent jewelry addition I’ve been loving. I grabbed it on a whim—also at Vestige—and have been dipping my toes into silver this year. It’s been a nice change in tone. I also bought an Apse ring earlier this year that’s now a daily staple.
Next up, here are a few actual outfits I managed to capture!
And finally, a little bonus edit: a handful of other items I’ve wishlisted or have my eye on, plus a new swimsuit pickup I totally forgot to mention earlier. I was drawn to the simple cut, dramatic back scoop, and cherry red color of this Lido one-piece. The back fit is a bit cheekier than I usually go for—but I ended up keeping it because the fabric feels amazing to the touch, and I’m a sucker for the fact that it’s produced in Italy.
Needless to say, I definitely have plenty of pieces to play with for my next tropical escape, but there’s always something fun about throwing a new item or two into the mix—it keeps packing from feeling too routine. For the most part I think I was able to strike a balance of staying true to my city girl style while leaning into the lighter energy of a resort setting.
Could you do a post on how you pack your carry-on? How do you fit so many shoes into a carry-on?