After spending a perfect day bathed in sunshine and enjoying poolside drinks with friends, it’s time to transition to your dinner attire. With breezy resort wear for women inspired by coastal trends and comfort, you can move between casual relaxation to upscale fashion with ease.
We’ve gathered our favorite vacation outfit ideas to take you from the beach to the table without missing a beat. From flowy skirts to activewear and everything in between, these day to night looks keep you looking stylish all vacation long.

1. The Effortless Maxi Dress
Long, lightweight and flowing, a maxi dress fits every resort occasion. Wear it for a stroll (and photos) on the beach, pair it with resort sandals and enjoy transitioning effortlessly from beach to boardwalk for evening cocktails.
For more formal resort fashion, dress up your maxi dress with jewelry and beaded sandals or slides. Choose bright-colored oversized necklaces to complement the hues of your dress, and pair with those shell earrings you picked up at a local jewelry shop that afternoon. Or, keep it classic with your usual gold or silver jewels that go with everything.
2. Coordinating Pants and Tank
Loose, comfortable pants, like the Laken Wide Leg Pant, feel just as breezy and soft as a skirt with a little more skin coverage. They’re an elegant and cozy addition to any vacation packing list.
Add your favorite tank or tee to your coastally inspired look, and transition right from a daytime excursion. Focus on bright, tropical colors for your day to night look, or choose more natural tones to celebrate the natural beauty of your surroundings.
3. Active Dresses
Some resort vacations are for relaxing, and others are for experiencing once-in-a-lifetime adventures. Combine casual resort wear with comfortable performance clothing when you pack a few active dresses in your suitcase.
With a tailored fit and enhanced performance fabrics, these dresses are perfect for tennis matches, a long walk through town or dinner in the resort restaurant. Slip out of your poolside sandals and wear strappy heels to instantly take this look from recreational to refined.

4. Flowy Skirt and Tank
Bring comfort to your beach vacation when you pair colorful tanks with skirts and skorts. This vacation outfit idea adds grace and style to your resort fashion sense, keeping you cool and casual without the need to change your clothes for dinner.
A fringed or beaded shawl brings this look from the afternoon sun to evening candlelight. Wrap your hair in a silk scarf for an extra touch of vintage charm, and add chunky earrings for a dramatic effect.
5. Versatile Cover-Up
You may not be able to wear your swimsuit to the resort restaurant, but the right cover-up doubles beautifully as a brunch or lunch outfit. Resort wear for women should include shirt dresses or other cover-ups that can change looks by buttoning or zipping them up.
To complete this afternoon look, slip out of your pool slides and into more formal sandals. Put your hair into a neat bun or keep it loose for those coveted beach waves.
Transition Your Day to Night Look
Your vacation suitcase doesn’t need to be packed full of clothing for you to enjoy versatile resort outfits. Just a few accessories and articles can turn casual ensembles into elegant resort wear. Follow these teams to freshen up a daytime resort look.
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If your resort is on the formal side, opt for blouses rather than tanks or tees to pair with pants or flowy skirts.
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Wear one part of a matching set by day, and complete the look by adding the second piece at night.
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Counteract the beach-and-sunscreen aroma of the afternoon with a spritz of fragrance right before you head to the restaurant.
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Pack two pairs of sandals in your beach bag: one casual pair for the sand, and another formal or beaded pair for the evening.
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Slip on a sweater or cardigan to enhance a daytime look, and to keep your shoulders warm in the night air.

Easy and Comfortable Resort Wear for Women
These vacation outfit ideas are just a few ways to ensure you look and feel great for every occasion, whether you’re sipping mai tais on a lounge chair or Chardonnay in the resort bar. The best part? They work just as well in any tropical trip, whether you’re planning an off-season beach vacation or looking for your next holiday getaway destination. Add them to your vacation packing list to enjoy comfortable, breezy resort wear anywhere you roam.