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The Basics of Resort Wear

resort wear outfit
Top: Forever 21 (similar here), Pants: Eileen Fisher (similar here), Hat: Tenth Street Hats, Necklace: oNecklace, earrings: Madewell (similar here), Sandals: FitFlop, Bag: MadeTerra

Resort wear is what we call the interseason collection of travel clothes for those leaving a cold climate and heading somewhere warm. The term is a bit retro, but the idea is still current. Right now — in the dead of winter — I have many clients packing their bags for Barbados, Cancun, Cuba, Bali, Australia, and beyond. I know some of you are doing the same, so let’s talk about what’s going in your suitcase.

The best resort wear is all about breezy, lightweight outfits that can seamlessly transition from the beach/pool to dinner or a walk around town. I often use resort vacations as an excuse to try something new on my clients. It’s the perfect time to dress a little bit more sexy, colorful, or eccentric. After all, you’re on vacation! Below I have outlined the best resort wear pieces and outfits you must pack for your escape-from-winter travel.

For a list of my favorite year-round resort wear designers, read my post on My Go-To Resort Wear Brands.

Resort Wear Must: Hat

best resort wear
Lack of Color $90

Paradise tends to be sunny and you need a hat to protect your eyes, skin, and hair from the rays of that beastly goddess. I tend to favor hats with structure versus floppy hats. Yes, they are harder to travel with since you can’t just crumple them up in a suitcase, but geeze Louise, those “packable” hats look like shit when you take them out of the suitcase. To travel with a structured hat, I use the Lindsay Albanese hat holder to clip my hat to my bag. If you really need a good packable hat, I highly recommend San Diego Hat Company’s signature roll-up visor.

Available at Nordstrom, Revolve, Zappos, and Lack of Color.

Sizing: S-XL

Material: Palm-leaf straw

Resort Wear Must: Killer Sunglasses

best resort wear
Aire $50

You gotta have killer shades for your resort stay. Again, try something you may not usually rock. I love to select a bigger look, often in an usual color, when preparing my clients for a resort stay.

Available at Revolve.

Sizing: One size

Material: Acetate frames with translucent lenses

Resort Wear Must: Stunning Sarong

best resort wear
Johanna Ortiz $295

I want everyone to have an absolutely exquisite sarong. A sarong is so versatile for a vacation and one of the best resort wear items you can pack. You can use your sarong:

  • As a swimsuit coverup
  • As a dress if you are going straight from the beach or pool to dining
  • To cover your shoulders from the sun or a chill

My favorite one pictured above is lovely, but my second favorite by Maaji is more affordable and ready to shop right now.

Available at Neiman Marcus, Net-A-Porter, and Revolve,.

Sizing: One size

Material: 100% cotton

Resort Wear Must: Throw On Garment

resort clothes
L*Space $139

You must have a dress or garment that is easy to throw on for breakfast, a romp to the beach, or whatever quick thing you need to get dressed for on a resort vacay. I love this coverup dress above because it can go over a swimsuit or a simple bralette and makes for an easy and chic resort outfit. Another favorite is Show Me Your Mumu’s crochet coverup dress, which comes in so many different colors you can easily find one to match your resort wear wardrobe. (You can see me wearing the rainbow version here.)

Available at Revolve, Shopbop, and Anthropologie.

Sizing: XS-XL

Material: 85% viscose, 15% cotton

Resort Wear Must: Chic Swimsuit

best resort wear
Free People $168

Always pack multiple swimsuits. I love to pack a couple of two-piece suits for a better tan, and then one-piece suits for hanging around and more sporty activities. Either way, you must coordinate your suits with your sarong, throw-on dresses, and wide-leg pants. If you are packing right, you should be able to really move these pieces around with your swimwear for a cohesive look and easy outfit changes.

Available at Free People.

Sizing: XS-XL

Material: 90% Recycled Polyamide, 10% Elastane

Resort Wear Must: Bold Beachy Dinner Look

resort clothes
Just Bee Queen $650

One of my favorite resort wear outfits is a bold, beachy dinner look. At least one night you want to dress up in such a way that looks like you are ready for the beach, yet it is utterly stunning. Just Be Queen is one of my favorite designers for this type of look. For all my favorite resort wear designers, see my post on My Go-To Resort Wear Brands.

Available at Bloomingdale’s.

Sizing: XS-XL

Material: 100% linen

Resort Wear Must: Breezy Wide Leg Pants

resort wear pants
Faithfull the Brand Top $139 $74, Pant $179 $169

A breezy wide leg pant is a definite must for resort wear. The style is great for sun protection and the lightweight fabric keeps you from overheating. You can wear them casually, or throw them over a swimsuit to sport for dinner.

Available at Revolve, Bloomingdale’s, and Faithfull the Brand.

Sizing: XS-XXL

Material: 100% rayon

Resort Wear Must: Minimal Comfy Sandals

best resort wear
Bared Footwear $149

I would love it if those beautiful resort sandals were comfortable, but they are not, so I am all about keeping it super simple and utilitarian on the feet with comfy sandals. I also prefer to pack as much water-friendly footwear as possible. These sandals by Bared Footwear are my go-to resort sandals at the moment. They come in so many different colors, I am sure you can find one to complement your resort wear outfits.

Available at Bared Footwear.

Sizing: 5-12M (US)

Material: Natural rubber

Resort Wear Must: Crossbody Bag

best resort wear
Clare V. $375

I am all about a crossbody bag for travel, especially when you want to easily carry personal items around a resort or hotel. I am tickled pink I found a rattan crossbody bag to go with this resort post!

Available at Clare V.

Sizing: One Size

Material: Leather

Resort Wear Must: Wood Earrings

best resort wear
Casa Clara $48

If you wear earrings, you must pack a unique pair. Gold is lovely with all these resort pieces, of course, but I tend to favor an earthier material, like wood, as a nod to the magic of nature that often surrounds a resort vacation.

Available at Revolve and Madewell.

Sizing: One Size

Material: Wood

Resort Wear Optional: Off the Shoulder Dress or Top

resort clothes
Nation Ltd. $160

I know my busty gals don’t love to wear an off-the-shoulder top, but for those who feel comfortable, an off-the-shoulder top or dress screams resort wear chic. Plus, it helps keep unwanted tan lines away.

Available at Nation Ltd.

Sizing: XS-XL

Material: 100% Pima, Cotton Poplin

Resort Wear Optional: Chic Packable Tote Bag

best resort wear
Hat Attack $198

If you are doing some serious beach or pool lounging, you must have a chic packable tote bag for your towel, book, and other larger items. This is also great if you are shopping in the town. If you want to save space, I recommend chic reusable tote bags. I love this large tote bag from Clare V or this smaller stylish reusable bag from Anthropologie.

Available at Shopbop, Amazon, and Hat Attack.

Sizing: One Size

Material: Raffia

Resort Wear Optional: Statement Bag

best resort wear
L*Space $88

These bags usually don’t make sense, but they are just so cute and seriously polish off a solid resort wear outfit. The bag I selected above is lightweight, fits nicely on your wrist, and packs well. It looks fabulous for a dinner out.

Available at Revolve, Amazon, and L*Space.

Sizing: One Size

Material: Wood

Photos by Dayley Photography 

resort wearSan Diego style San Diego style resort wear

My blog posts are my honest and personal opinion. Sometimes my content includes products sent from brands or PR firms. In this case, I was sent a sample from Made Terra, Onecklace, Fitflop, and Tenth Street Hats. 

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