Your Resort Packing List, According to a Stylist
March 20, 2026
We’re all about helping you look your best, wherever you are in the world. Here’s what to pack for a resort vacation (for spring break and beyond), according to contributing fashion editor Cynthia Cook Smith.
Meet Our Expert:
Cynthia Cook Smith
During her time at Vogue, Cynthia worked behind the scenes at everything from fashion shows to the Met Gala, helping dress people for major events. Ten years later, she now styles clients for special occasions and everyday life.
Resort Style, Explained
The Signature Style:
Breezy and boho, it’s a laid back look that keeps things fresh and fun with bold prints and fun colors. Some natural elements, like raffia, are pulled in.
Our Fashion Fundamentals:
Keep it easy with classics that you can wear after vacation. Think a where-everywhere dress, swim, and matching set.
What to Pack for a Resort Getaway
With 25 pieces you’ll wear throughout your stay, we’ve got everything you need organized by category.
DRESSES
Flowy Maxi Dress
Shift Dress
Slip Dress
Knit Black Dress
TOPS
Linen Button Down
Tank
Flowy Blouse
BOTTOMS
Shorts
Linen Pants
Printed Pants
Long Poplin Skirt
SWIM
Classic One Piece
Printed One Piece
High-Waisted Bikini
Caftan
Matching Set
FOOTWEAR
Leather Sandals
Dressy Sandals
Espadrille Wedges
ACCESSORIES
Sunhat
Straw Tote
Clutch
Statement Necklace
Sunglasses
Printed Scarf
Our Top 5 Packing Tips
Bring a Black Dress
So simple, yet so elegant. Throw it over a swimsuit or wear it to dinner.
Pack a Matching Set (or Two)
Matching sets take the guesswork out of dressing. Bonus: you always look put-together.
Pair Jewelry With Swim
Don’t be afraid to dress up yourone piece with a necklace or earrings.
Wear Your Suit on the Town
Don’t let your suit sit by the pool. Pair with a maxi skirt and wear it to lunch.
Finish With Raffia Accents
A raffia beach tote or shoe brings the island feel.
Ready to explore? Here’s what to pack for everything.from a day by the pool to cocktails by the beach.
Morning Coffee Run
Look like a local in an easy, effortless tank paired with a fun pair of printed pants. A big necklace is the best finishing touch.
Lounging by the Pool
Spend your day reading a book or chat with friends old and new in a swimsuit styled with a statement necklace, woven bag, and colorful sandals.
Lunch
A quick lunch at a local spot needs a throw-on-and-go dress. A black knit is effortless and always chic. Bonus: you can wear it long after the vacation is over.
Boat Ride
All aboard! A matching set makes getting ready mindless. Cynthia’s loves this stripe set with a red swimsuit underneath for an updated nautical nod.
Cocktails by the Beach
Get drinks with friends in gilded glam. This matching set gets a tropical treatment with a mariner’s link bracelet and a raffia bag.
Fancy Dinner
An elegant meal deserves a bold, yet sophisticated look, like this red linen dress from Zimmerman. It has a silk tie belt that makes it truly special.
FAQs
Why do we love resort season?
Everyone deserves time to sit back and relax, and resort season lets you. Whether you’re going to Palm Beach, St. Barts, Bermuda, or somewhere else in the world, resort style celebrates a laid back and relaxed place of life that brings sunshine and joy.
What’s the weather like?
It depends on where you go! Do you research and look up the weather before you pack. These looks are styled with warm weather (between 75 and 90 degrees) in mind.
What are three things I have to pack for a resort trip?
Our non-negotiables: a little black dress, a pair of designer sunglasses, and a matching set that doubles as a day look and a cover up.
What’s a packing list?
A packing list is a tool that helps ensure you have everything that you need packed and ready for your destination. Let us help you plan your outfits and simplify your packing.
Get Inspired:
#Tuckernucking, Resort Style