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.

Chan Luu Top, Marta Ferri Skirt (old, similar here, here & here), JB x Margaux Sandals, Sensi Studio Bag, Retrosuperfuture Sunglasses

Evening looks are the pieces I get most excited about when I’m packing for a warm-weather trip. Something shifts once the sun goes down. Vacation dressing gets to be a little more expressive, a little more vibrant, a little more fun. Sequins for sunset drinks, a flowy dress for a late dinner that has a way of turning into a longer night… almost nothing feels off-limits when it comes to dressing for evenings away from home.

The trick, for me, is starting with one piece that feels particularly special. Something with a little sparkle, a saturated color, or a more playful silhouette than I usually reach for. From there, the rest of the outfit falls into place around it. A skirt with shine works best paired with a clean top that lets it do the work. A dress with dramatic draping and a floral print wants modern, pared-back accessories. A sandal with a playful embellishment can be the whole story, peeking out from under a relaxed pant.

The result is dinner dressing that feels festive without trying too hard, and ready for the kind of night that keeps going.