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What’s “Resort Wear” Anyway?

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Resort wear // Derek Lam Navy Grommet Crop Top with Diane von Furstenberg Charli Trousers, Splendid Billie Espadrilles, and Lo & Sons The Pearl crossbody in plum
Photo Credit | Sean O’Neill

A steady diet of Harper’s Bazaar as a teenager meant that I always looked forward to two times of the year – the fall style issue, and the resort wear issue. While the former was always plush with velvets, jewel-tones, and – my favorite – rich woolens – the latter was usually a delightful feast of crisp whites and flowy separates.

It’s only now that I talk about fashion out loud to people that I’ve found resort wear is a bit of a niche term. Quite literally, it’s the post-winter fashion you wear to your warm-weather resort destination after the holidays. For me, there are three essentials for spring getaways – flowy white pants, a vintage-inspired bikini, and a versatile crossbody bag.

Here’s a set I shot with Miami photographer Sean O’Neill showing off these three staples from my wardrobe. Thank you to Sean for collaborating with me on these looks!

The flowy white pants

Resort wear // Derek Lam Navy Grommet Crop Top with Diane von Furstenberg Charli Trousers, Splendid Billie Espadrilles, and Lo & Sons The Pearl crossbody in plum

I fell in love with this navy Derek Lam top as soon as I received it from Rent the Runway. It’s a perfect slightly cropped length, and an elegant black grosgrain ribbon runs through the grommets around the collar and hem. This detail softens the hardware, and the combination of navy and black makes it versatile.

I picked up this hat at an outdoor market in the Wynwood neighborhood. It’s the first “everyday hat” I’ve ever purchased. I spontaneously added it to this look and I’m glad I did – it balanced the white pants (and kept the sun off my face).

Resort wear // Derek Lam Navy Grommet Crop Top with Diane von Furstenberg Charli Trousers, Splendid Billie Espadrilles, and Lo & Sons The Pearl crossbody in plum

Pants | Diane von Furstenberg Charli trousers – sold out, but similar here and here Top | Derek Lam 10 Crosby navy grommet crop top via Rent the Runway – use my referral code for $30 off your first RTR order! Shoes | Splendid Billie Espadrilles

The vintage-inspired bikini

Resort wear // Summersalt the classic high rise bottoms and the sidestroke top at the Faena Hotel Miami

This black and white two piece from Summersalt was an impulse purchase and I’m still deciding how I feel about it. The top doesn’t have a clasp at the back so you have to pull it on and off which is a little uncomfortable. On the bright side, it looked fantastic in these shots Sean took at the Faena Miami Beach hotel.

Summersalt the classic high rise bottoms and the sidestroke top on Miami beach. Photo Credit | Sean O’Neill
Resort wear // M. Gemi Merita slides at the Faena Hotel Miami

Swimsuit | Summersalt the classic high rise bottoms and the sidestroke top Sandals | M. Gemi slides – use my referral link for $50 off your order! Sunglasses |Warby Parker

The versatile crossbody bag

Resort wear // Lo & Sons Pearl crossbody in plum

I like experimenting with wearing the same color in a couple different shades – there was something about this plum Lo & Sons crossbody against the slightly warmer wine tank top that felt unique and fresh. Neutral pants (and nails) ensured it wasn’t color-overload.

Resort wear // Miami Carven Bordeaux V-Neck with Diane von Furstenberg Charli Trousers
Bag | Lo & Sons The Pearl crossbody in plum Top | Carven Bordeaux V-Neck – sold out, but here’s a similar one from Grana – use my referral link to get 10% of your first order.

Call me crazy, but this is my third Lo & Sons Pearl bag, which I also have in black and light grey. It really is perfect – it transitions from a crossbody to a clutch and has separate pockets to keep everything you need organized.

What are your go-to resort wear pieces? Tell me in the comments!

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