My Favorite Vacation Dresses and Shoppable Outfits You’ll Actually Love to Wear.

Packing for a tropical vacation should be fun—but finding outfits that are both photogenic and practical? That’s a little more complicated. I’ve learned that the best vacation wardrobe is filled with pieces that feel good, photograph beautifully, and easily go from beach to dinner.

Whether you’re headed to the Caribbean (like my recent Grenada girls’ trip), Europe, or just booking a staycation with island vibes, here are a few of my favorite looks for warm weather escapes—all linked so you can shop them directly.

For Sunset Dinner: The Statement Floral Maxi

Nothing says “vacation mode” quite like a floaty floral dress. I wore this Bergamot Orange Floral Print Satin Sweetheart Maxi Dress by Club L on a night out and it turned heads. The sweetheart neckline and silky satin finish give it a luxe feel, while the bold tropical print makes it perfect for golden hour photos.

Pair it with minimal gold jewelry and strappy heels—or dress it down with slides for an effortless dinner look.

For Exploring Towns or Markets: The Flowy Midi

A breezy white eyelet midi dress is my go-to when I want to look polished but stay cool. It’s ideal for market strolls, brunch dates, or afternoon cocktails on the beach. Bonus: it layers well with a denim jacket or lightweight cardigan for cooler evenings.

Shop a more affordable version: White Eyelet Midi Dress

For Day Trips & Island Adventures: The Versatile Set

Matching sets are my secret weapon for travel style. This linen two-piece set is breathable and stylish, and you can mix and match the pieces throughout your trip. I love the tailored look with flat sandals during the day and a woven bag to keep it chic.

Shop it: Linen Matching Sets

For the Beach or Poolside: The Bold Cover-Up

A cover-up that works hard is key. I love something like this sheer button-down beach shirt or this black button-down beach shirt that doubles as a top over shorts or a chic throw-on after a swim. The bold color pops against blue water and golden sand—exactly what you want in photos.

Shop it: Beach Shirt Cover-Up

For Drinks at the Resort Bar: The Vibrant Mini

This hot pink midi dress is a vibe. Perfect for dinner, dancing, or just feeling fabulous. I love pairing it with platform sandals and a bold lip for a night out—or layering it over a swimsuit for a fun après-beach look.

Shop it: Pink and Orange Maxi Dress

Final Thoughts: Vacation Style Should Feel Effortless

When I pack for a trip, I always ask: Can I move in it? Will I feel confident in it? Can I style it more than one way?

Each of these pieces checks those boxes—and they’ve all made my packing list more than once. If you’re building your dream vacation wardrobe, start with a few versatile dresses, a statement piece or two, and elevated basics you’ll want to wear again and again.

 

Browse the full collection:
Shop My Vacation Outfits Here