With snowflakes swirling in the forecast and the chill of New York’s winter setting in, the idea of basking under a hot sun with a margarita in hand feels irresistible. When the city is bundled in gray, nothing sounds better than trading layers of wool and puffer coats for flowing dresses, sandals, and the salty kiss of an ocean breeze. For me, a quick escape to somewhere warm—Puerto Rico or Miami, perhaps—is just the dose of sunshine I need before diving headfirst into the whirlwind that is New York Fashion Week.
And yes, my bags are already packed.
A Versatile Vacation Hero
When it comes to curating a resort wardrobe, I look for pieces that can transition seamlessly from beach strolls to dinner under the stars. That’s why I am smitten with the red floral caftan frock from ASOS—a dress that practically does it all.
What makes it so perfect? For starters, it’s bold and breezy. The oversized floral print feels festive yet timeless, and the silhouette is effortless, giving off that chic “I just threw this on” energy we all aspire to when on vacation. It’s the kind of piece that works for morning market browsing, poolside cocktails, and even a night out dancing.
The caftan comes in sizes 0 through 14, but let me give you a little insider tip: it runs quite roomy, so don’t be afraid to size down. The dress includes a slip, though you can easily swap it out for another one from your closet if the fit feels snug. I especially love that the size 14 can comfortably fit up to an 18/20 when worn without the slip, making it a versatile choice for more body types.
And the best part? It retails for just $87 on ASOS, which makes it an affordable hero piece for your suitcase. If florals aren’t your thing, there’s also a solid red version that’s equally striking.
The Dream Shoes
Now, no vacation outfit is complete without the perfect sandals. I’ve been living for the Tabitha Simmons Avary sandals—a dreamy pair that manages to strike the balance between polished and playful. They’re lightweight enough for strolling cobblestone streets yet elegant enough to pair with a dress for dinner al fresco. Even better, they’re currently on sale, which makes the investment a little easier to justify.
Shoes are often the unsung heroes of a vacation wardrobe, but the right pair can make or break your trip. My advice? Choose one elevated sandal that can dress up a casual look and one practical pair for days filled with exploring. With those two in your bag, you’ll be covered for just about anything.
Why Resort Wear Feels Like Magic
There’s something about resort wear that feels more liberating than any other category of fashion. Maybe it’s the colors—sun-drenched reds, ocean blues, tropical greens—or maybe it’s the silhouettes, which flow and move with ease. Resort wear gives us permission to play, to embrace joy in what we wear.
During winter especially, these pieces feel like a rebellion against the monotony of black coats and chunky sweaters. They remind us that somewhere in the world, the sun is shining, the water is warm, and life is being lived in Technicolor. Packing for a beach getaway isn’t just about preparing outfits—it’s about shifting into a mindset of relaxation and celebration.
Packing for Every Occasion
When curating your suitcase, versatility is key. I always recommend focusing on pieces that transition from day to night, like the ASOS caftan. Add to that a couple of lightweight sundresses for daytime exploring, a chic maxi for evening, and a fun, flirty option for nights when you’re ready to hit the town.
If you’re looking for more inspiration, my What to Pack for a Winter Beach Vacation post dives deeper into resort wear, with an edit of dresses that work for both day and evening. You’ll even find some sexier options for those late-night adventures when the beach transforms into a dance floor.
And don’t forget your accessories. Oversized sunglasses, statement earrings, and a woven tote instantly elevate even the simplest dress. A wide-brimmed hat not only protects you from the sun but also adds that effortless glam factor.
Final Thoughts
As winter settles in and New York is blanketed in snow, I can’t think of anything more indulgent—or more necessary—than escaping to a warm destination. Whether it’s Puerto Rico’s vibrant beaches or Miami’s sizzling nightlife, the key to making the most of a getaway lies in your wardrobe. Pack pieces that make you feel confident, comfortable, and ready to embrace every moment.
For me, that means slipping into a red floral caftan, strapping on those dream Tabitha Simmons sandals, and stepping into the sun with nothing on the agenda except relaxation. Because sometimes, the best way to beat winter is with a suitcase full of color, a glass of something tropical, and a heart wide open to adventure.
