A long weekend somewhere warm asks for very little: a dress for lunch, something easy for the afternoon, and one piece that feels like an occasion at night. Pack around those three moments and the suitcase takes care of itself.
Day one: arrive in a dress that does the work
Travel days are for pieces that look finished without effort. The Joanna Shirt Dress in Cabana ($495) has bell sleeves, a flounced skirt and a removable sash, so it reads polished at the airport and relaxed by the water. Add flat sandals and a straw hat, and you're dressed for a late lunch the minute you land.
Day two: a skirt you can style three ways
One printed maxi skirt stretches further than three extra tops. The Lizzie Maxi Skirt ($395) comes in several prints, from the soft Callista Palm to the bold blue Dane. Wear it with a white tank by the pool, a lace blouse like the Cenia Sleeveless Lace Blouse ($148) for dinner, or tuck in a plain tee for a walk into town.
Day three: easy daytime dresses
For brunch and afternoons, reach for dresses you don't have to think about. The Barbie Midi Dress in Bluebell ($465) has small blue florals, a straight-across neckline and a mid-calf length. The Kendall Mini Dress in Palisades ($345) is shorter, with pleats at the shoulders and an optional sash, and pairs with sneakers as easily as sandals.
The evening piece
Keep one dress back for the dinner that matters. The Bardot Dress in Dane ($495) has a bold blue-and-white print, lace trim and a V-neck. It needs nothing more than gold earrings and a clutch.
The packing list
- 1 shirt dress for travel day
- 1 printed maxi skirt, plus a white tank and one dressier top
- 1 or 2 easy day dresses
- 1 evening dress
- Flat sandals, one heel, a straw hat and a small bag
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