Evening Resort Wear for a Beach Vacation Dinner

Dear Deborah,

For our vacation, we’re going to a really nice beach resort. Can you suggest some resort maxi dresses or something else appropriate for dinner with friends? Something dressy but with a tropical or beachy vibe? Thanks, Jan.

Hi Jan,

Lucky you! It sounds like you’re going to have a fabulous time. Getting dressed up for a beautiful dinner after a long day at the beach is one of the most enjoyable parts of any vacation, which is why it’s so important to feel confident that you’ve packed just the right thing.

You seem to have a good idea of what you need! Dressy evening resort wear is simply a step up from casual but not as formal as cocktail or business wear. It’s elegant but relaxed and makes you look and feel like you are on vacation, even if you are not!

Evening Resort Wear for a Beach Vacation Dinner

I was recently in Florida, where I wore this chic resort maxi dress. It fits the bill. Have a closer look, and check out these tips for choosing the perfect evening resort wear.

1. Think Elegant, Feminine, and Flowy

Imagine sitting down to romantic dinner on the patio under a giant palm tree, watching the sun slowly set and listening to the ocean waves crashing in. This is not the time to wear a stiff, serious dress. You’re on an exciting getaway, so choose something light, feminine, relaxing, and effortlessly chic. If it moves when you move, all the better – something that will look beautiful blowing in the ocean breeze is perfect!

Shop the look

This airy chiffon animal print dress is a great example of what I mean. It’s loose, flowy, and a little wild! Chiffon is perfect in warm weather, but linen, cotton, and silk are also popular for resort wear.

This gorgeous dress has a big cat look and feel, but when you look up close, you see the print is actually a little abstract, making it modern.

Sexy sandals and a unique bag also elevate evening dinner resort wear, so I’ve paired this dress with beachy cork sandals and a chic cork purse (similar). I love how they enhance the exotic feel of this outfit.

Speaking of exotic, this brings me to another point about how to style evening resort wear…

2. Add Playful, Statement Jewelry and Accessories

Leave your conservative stud earrings at home and go for big, dangly, fun, colorful earrings and jewelry.  Bracelets and necklaces with fringe, beading, rattan, hammered metals, and unique stones tell a story.

For example, this bold Tiger’s Eye gemstone pendant has an exotic and exciting safari feel. The stunning, chunky chain necklace perfectly complements my edgy animal print dress. I love how it fills up the flattering V-neckline and elevates my maxi to a chic resort-wear look.

Since jewelry is a big part of resort wear style, I’ve added matching hammered gold drop earrings, a stunning mini gemstone cuff bracelet, and a beaded gold bracelet. These are all from Dean Davidson’s new Nomad collection, which is so good!

I’m ready for a beautiful evening of dinner under the stars at a 5-star vacation resort! Here are a few more tips for choosing elegant evening resort wear.

3. Tropical Prints  Always Look Right

Animal and safari-style prints are just one option. Bold prints like the one on this floral tunic maxi are also a huge part of the resort style. Bright, tropical flowers, foliage, exotic birds, and jungle prints are also natural choices.

Keep things classy by having one print as your focal point and leaving everything else neutral. For example, with this lively tunic dress, wear natural nude straw sandals.

4. A Halter Dress is Resort-Like

Any kind of dress that reveals a hint of skin, like an off-the-shoulder, high-slit, or this halter style dress, is perfect for a classy evening resort look. I love the stunning print on this beautiful blue halter maxi dress by Lilly Pulitzer. This has such an elegant but vacation-like feel to it. Can you imagine how perfect it would be for a Mediterranean cruise?

5. Have Fun with Color

Tropical temperatures = hot colors. Don’t be afraid to look festive in happy island colors like orange, yellow, hot pink, lime green, or bright parrot blue. You’ll fit right in.  Black is fine, too, especially a print dress that is black with colorful splashes of color.

6.  Let loose in a Comfy Jumpsuit

Dresses aren’t the only choice for a dressy dinner at a beach resort. Loungewear-style pants, like palazzo pants or this breezy Azure Palm jumpsuit, looks relaxed and classy.

7. Have Fun!

No matter what you choose, resort wear should be fun. It’s a great way to express your personality and enjoy some drama while on vacation. This opulent crochet maxi dress is amazing for gals who love to own the room! Enjoy.

I love the color of this stunning orchid one-shoulder maxi, which you could easily dress up with gold or silver jewelry!

Dressy Resort Style Summary

Let’s review the elements of dressy resort style:

• a step up from casual but not formal
• effortlessly chic, relaxed, comfy
• light fabrics like cotton, linen, silk
• elegant dresses, skirts, loose tops, pants (flowy is good)
• vibrant colors & prints
• beading, gemstones, hammered metal, summery embellishments
• lots of big, bold jewelry and accessories!

Enjoy your trip!

Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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