I Packed Like a Snowbird for My Winter Beach Vacation

As someone who most often dresses for Manhattan, I’m very intrigued by snowbirds—the folks who flee the northeast during the colder months to spend the season down in warmer climates. They’ve got a chunk of their wardrobe on reserve specifically for this, complete with bold patterns, beachy accessories, and vibrant but sophisticated dresses that make you question why you ever thought denim shorts were acceptable summer attire. What better inspiration for my own winter retreat down to South Florida?

Palm Beach has always been about looking the part—and its inhabitants are well aware. During my stay, I opted in on a walking tour of the renowned Worth Avenue, led by local impeccably dressed icon Rick Rose. As we weaved between historic landmarks and luxury boutiques, he shared that much of the architecture was intentionally designed to look varied, architect Addison Mizner insisting that intentional imperfections would give the street an older ambiance and mystique. It would be more chic that way.

Whether your interest is piqued by studying vintage Lilly Pulitzer prints or the lavish looks on Palm Royale, there’s no shortage of fashion inspiration in Florida’s most stylish city. So, for my own trip, I channeled my inner snowbird. Ahead, what I consider to be the must-have pieces in any tropical vacation wardrobe— plus, some shoppable options for your own potential Worth Avenue debut.

Tunics, Caftans, and Dresses Galore

(Image credit: Bella Gerard)

There’s nothing more classic Palm Beach than a beautiful patterned dress, be it a flowing caftan, an embellished tunic, or a sundress in a print that’s guaranteed to turn heads. The silhouettes are always modest and timeless, but when it comes to color and pattern, the more audacious, the better.

(Image credit: Bella Gerard)

I knew this Lilly Pulitzer caftan in El Morocco (one of the newly re-released vintage prints) would serve me well on my trip as an all-day ensemble. For everything from tea at The Brazilian Court’s Cafe Boulud to dinner at Sant Ambroeus, a great dress is a safe bet.

Straw and Rattan Details

(Image credit: Bella Gerard)

If you can add a straw hat or a rattan clutch to an outfit, best believe a Palm Beacher will. These natural materials ground the bolder prints and bright hues that make up so much of their wardrobes, creating perfect sartorial harmony. My own go-to was this black wicker clutch (pictured throughout) for evenings out—like a fantastic dinner at Harry’s—for which natural straw didn’t feel elevated enough. And as a melasma gal, I need many sunhat options for daytime.

Matching Sets

(Image credit: Bella Gerard)

Palm Beach style is all about looking chic and put-together, even when you’re drifting off to tan or popping into Le Bilboquet Market for provisions. For any occasion, a matching set is effortless and appropriate. And the best part? You can always break up the pieces and style them separately to improve your cost-per-wear.

Splurging on a set from LaDoubleJ, Alemais, or Zimmermann can be an investment that pays off in spades—but on the low, I often find amazing ones at H&M, like this black patterned pajama-style blouse and pant set I wore right off the plane to dinner at RH Rooftop.

Party Pants

(Image credit: Bella Gerard)

I’d argue you can never be too bold in Palm Beach, but if a patterned matching set feels overwhelming, keep your top half super simple and your bottoms bright. Funky party pants with a plain top and some good accessories—more on those next—are as good a going-out ensemble as it gets.

Here, I’m wearing some Farm Rio pants (almost sold out!) with a black tube top from Aritzia to match the fun vibes at Gabriella’s Modern Italian in downtown Delray.

Amped-Up Accessories

(Image credit: Bella Gerard)

While I nailed my snowbird wardrobe (is this Palm Beach-printed dress not proof?), I found myself severely lacking in accessories as I surveyed the stylish women surrounding me in Palm Beach. More is more is more, it seems—especially when it comes to chunky earrings (save your lobes and go clip-on!), pendant necklaces, bangle bracelets, and statement sunglasses. Trust, I’ll be packing a separate carry-on for finishing touches on my next trip—or bringing an empty one to fill up on Worth Avenue.

Hair Wraps and Headscarves

(Image credit: Bella Gerard)

I donned this Lilly headwrap to match one of my dresses, and while the combo intimidated me at first, it ended up being one of my most-complimented looks of the trip. A silky scarf is a must in Palm Beach to channel retro beauty vibes, as illustrated throughout the new season of Palm Royale, whether tied up as a turban à la Norma Dellacorte or wrapped kerchief-style around the hair like Maxine Dellacorte-Simmons.

I also always bring a vintage Hermès scarf on trips like these to remedy bad hair days. (Pre-loved retailers like Fashionphile always have the prettiest prints available at a discount.) Mine made it so that I could transition effortlessly from the pool to a visit to the Flagler Museum without having to wash and style my hair. How’s that for a chic time-saver?