Bondi Born Bikini, Julia Amory Pants, Magda Butrym Scarf

The best days on vacation follow no schedule at all. The morning starts slow, no pressure to get dressed, and somehow you’ve ended up in a bikini on the beach by the time you’ve finished your second cup of coffee.

Then comes the in-between hour. You’re either heading to lunch, or just stretching a day of leisure a little further. The afternoon doesn’t call for a full outfit change, but you want to feel a touch more put together.

Zimmermann Bikini, Soleil Soleil Pareo, Retrosuperfuture Sunglasses, Missoni Headband (available here) | Juilet Bikini, Soleil Soleil Pareo, Janessa Leone Hat

A floral pareo tied at the waist. Gauze shorts after the pool. A crochet mini dress for padding around the house before heading back out. These are the in-between pieces that stretch a vacation wardrobe all day long. Suddenly you have an outfit without the pressure of getting dressed.

To complete the look, a wide-brimmed hat, green sunglasses, or a striped headband. These are the finishing touches you reach for between swims, keep them on through lunch, and somehow they’re still on when the sun starts to drop.

Co Dress, Britt Netta Sandals, Dezso & Rebecca de Ravenel Necklaces (similar here), Vin Bag

To me, a statement dress is one that makes you pause for a second. The color, the shape, some interesting element of texture grabs your attention and feels like it starts a conversation.

When I’m considering one for my wardrobe, I ask myself, “Where can I picture myself wearing this?” There’s something about it that turns the everyday act of getting dressed into the best part of the night, before you’ve even thought about a shoe or a bag.

My test is simple: it has to feel distinct from the dresses already hanging in my closet, the ones I reach for on any given night out to dinner or to grab a drink. Whether it’s print and raffia fringe that feels like it can only really exist on an island, or all-over lace with beaded appliques, there’s something about it that feels like the drama has been turned up. That’s my standard: it doesn’t just get you through the night, it becomes part of the story.

Matching sets are one of the easiest things to pack. No styling math, no digging through a suitcase for pieces that work together — just a top and bottom that immediately feel like a complete look. That’s part of why they make up so much of my vacation wardrobe, the styling can go in so many directions. A printed silk set for hotel breakfast and a walk through town. Crochet shorts and the matching top for poolside lunches, beach clubs, or anywhere with tiled floors and wet hair. A fringed knit skirt and tank for sunset dinners, or embroidered cotton pieces for market mornings that turn into an afternoon of shopping.

Bring a few base pieces along and a set becomes more than one outfit. Wear it together when you want the full effect, then split it up later in the trip with a simple tank, linen pant, or white shorts. That’s what makes them such a good packing move — complete right away, but still room to play.