I have a bad habit. Every January, when the sky outside is the color of dishwater, I start planning outfits for trips I have not even booked yet. My sister calls it “vacation cosplay” and honestly she is not wrong.
It started a few years ago when my friend Dana came back from a beach holiday with a suitcase full of dresses she never wore because she “was saving them for the right night” that never came. I promised myself I would never do that. So now I plan looks that are easy, wearable, and just a little bit chic.
So here are 20 outfit ideas for your next warm-weather getaway.
20 Breezy Island Looks Worth Packing First
Turquoise Sundress With Beaded Sandals
There is something about a turquoise dress that just belongs by the water. It matches the sea, it makes your tan look better, and it photographs like a dream. Add a pair of beaded sandals and you are done.
I wore something almost exactly like this to a birthday lunch last spring and got compliments the entire afternoon. The beaded sandals are the little detail people notice. And they are comfortable enough for cobblestone streets, which matters more than you think.
White Crochet Dress With Raffia Tote
A white crochet dress is one of those pieces that looks expensive even when it isn’t. It works over a swimsuit or on its own for lunch. Pair it with a raffia tote big enough for your book, your sunscreen, and the pastries you told yourself you would not buy.
I have a friend named Claire who packs exactly one white crochet dress for every trip and rewears it constantly. Smart woman.
Tropical Print Maxi With Flat Sandals
Sometimes you just want to lean ALL the way into the tropical vibe, and a printed maxi dress is how you do it. Big bold flowers, greens and pinks, the whole thing. Some of the best belize outfits I have planned start with a maxi like this because it moves so nicely in the breeze.
Flat sandals keep it walkable. And a maxi hides a lot after a big dinner, which I appreciate more with every passing year.
Linen Bandeau Top With Palazzo Pants
Palazzo pants are secretly the comfiest thing you can wear that still looks put together. Pair them with a simple linen bandeau top and you have a look that feels breezy and a little bit polished at the same time.
This is my go-to for a warm evening when I want to be comfortable but not sloppy. Add some gold hoops and you are set.
Eyelet Mini Dress With Woven Accessories
Eyelet fabric is just so sweet and summery. A little eyelet mini dress in white or pale yellow feels fresh, and it pairs beautifully with woven accessories: a woven bag, woven flats, maybe a woven headband if you are feeling it.
Keep the jewelry small. The texture of the eyelet and the woven pieces is already doing the work.
One-Piece Swimsuit With Sheer Sarong
A good one-piece is worth the investment. I know they cost more than they used to, but a flattering one-piece with a sheer sarong tied at the hip is a look I reach for again and again. It takes you from the beach chair to the beach bar snack shack without a costume change.
The sarong does not have to match perfectly. In fact, a slightly clashing print looks more collected, not less.
Teal Halter Dress With Shell Jewelry
Shell jewelry is having a moment and I am so happy about it. A teal halter dress with a shell necklace and matching earrings feels like a summer memory in outfit form. So easy, so pretty.
My daughter borrowed my shell necklace last summer and never gave it back. I bought myself two more out of spite. Worth it.
Striped Shirt With Drawstring Trousers
For the days when you want to look like you are effortless (even though we all know nobody actually is), a classic striped shirt with soft drawstring trousers is the answer. It reads a little coastal, a little Riviera, and it comes together in about four seconds.
Roll the sleeves. Add flat sandals. Done and done.
White Poplin Dress With Jelly Sandals
Crisp white poplin is the fabric of good vacations. A structured white poplin dress feels clean and cool even in the humidity. And jelly sandals, yes the plastic ones, are back and honestly perfect for a beach town where your feet get wet a hundred times a day.
I resisted jelly sandals for years. Then I gave in on a trip and now I own three colors. Never say never.
Crochet Top With Printed Maxi Skirt
Mixing a simple crochet top with a bold printed maxi skirt gives you the best of both worlds: texture on top, movement on the bottom. It is a great way to break up a full print so it does not feel like too much.
This combo works for a beach dinner and a market morning equally well. I love a piece that pulls double duty.
Aquamarine Co-Ord With Raffia Bag
A matching set, or co-ord, is the lazy person’s secret to looking coordinated (guilty). An aquamarine co-ord in a light knit or linen with a raffia bag is one of my favorite grand cayman outfits to imagine, because the color looks so good against that particular shade of water.
The best part about a co-ord is you can split it up later and wear the pieces separately. Two outfits, one suitcase slot.
Red Sundress With Mesh Ballet Flats
Red on vacation is a statement, and I am here for it. A simple red sundress with a pair of mesh ballet flats is chic in that way that looks like you did not try. But you did. We always do.
Red just photographs beautifully against sand and blue skies. And mesh flats breathe, which your feet will thank you for.
Linen Vest With Matching Bermuda Shorts
A linen vest paired with matching Bermuda shorts is one of those grown-up looks that feels fresh and a little bit sharp. It’s polished enough for a nicer lunch but still cool and comfortable for warm afternoons.
Printed Kaftan With Embellished Sandals
The kaftan. The unsung hero of every warm-weather trip. Throw a printed kaftan over your swimsuit and you can wander anywhere without thinking twice. Add embellished sandals with a little sparkle and suddenly it reads dressy.
Kaftans are forgiving, breezy, and fold up to almost nothing in your bag. I pack at least one on every trip.
Black Swimsuit With Linen Beach Pants
A black swimsuit is a workhorse. Pair it with loose linen beach pants and you have a look that goes from the sun lounger to a casual dinner without much effort. So simple, but it always works.
Linen pants over a swimsuit is a trick I learned from my sister years ago and I still use it constantly. Cool, breezy, and it hides the fact that you are technically still in your swimsuit.
Broderie Blouse With Tropical Print Skirt
A pretty broderie blouse, all that lovely cutwork detail, paired with a tropical print skirt is such a happy mix. The white blouse calms down the loud skirt, and the whole thing feels romantic without being over the top.
Tuck the blouse in loosely. A little bit undone is the goal here.
Nightgown Mini Dress With Beaded Bag
The slip-style, nightgown-inspired mini dress is one of my favorites for a warm evening. It feels soft and pretty, and a little beaded bag adds just enough sparkle for dinner. Some of the prettiest all inclusive resort outfits I have put together started with exactly this kind of easy slip dress.
Keep it barefoot-adjacent with delicate sandals. The dress is doing the talking.
Halter Top With Flowing White Skirt
A halter top with a long flowing white skirt is breezy in the best way. It catches the wind, it swishes when you walk, and it just feels like a warm night should feel.
I wore this to an outdoor dinner last summer and spent half the meal watching the skirt move in the breeze. Silly, maybe, but that is the joy of it.
Colorful Crochet Dress With Woven Slides
If the white crochet dress from earlier is the classic, then a colorful crochet dress is its fun cousin. Pick a bright coral or a sunny yellow and pair it with woven slides. It is playful and a little bohemian and so easy to throw on.
Colorful crochet is one of those things that looks like too much on the hanger and just right on. Trust it.
Silk Scarf Top With Relaxed Linen Pants
Last one, and a favorite. A silk scarf top, the kind tied at the neck or back, paired with relaxed linen pants is such a chic, easy combination. It feels a little glamorous without any effort at all. Between this and a printed slip, planning my curacao outfits and even my anguilla outfits basically writes itself.
The silk catches the light beautifully in the evening. Add small gold jewelry and you are ready for anything.
