What to Wear: For 7 Scenarios on Your Calendar This Season
Written by: Amanda Chung
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Published on: May 9, 2023
Fashion editor: Ali Pew
CARA CARA DRESS, goop, $395
It’s almost Memorial Day (how did that happen?), which means it’s time to get outside and start enjoying ourselves. And that means that we don’t want to spend precious time standing in front of the closet trying to figure out what to wear. To that end: We’ve put together looks for seven scenarios—each of them adaptable to a variety of events on your seasonal calendar. Best friend’s birthday? Please see The Theme Is: Neon. Cousin’s wedding? That would be Love Is in the Air. Last-round interview for your dream job? You Mean Business is your look book. Scroll through, get inspired—and then get out there and enjoy the season.
WHAT TO WEAR WHEN…
YOU’RE ON VACATION
Keep the aesthetic of your destination in mind. Jetting off to Positano? Lean into sumptuous silks, limoncello yellow, and joyful maximalism with a print-forward pool look. If Majorca is more your speed, opt for a billowy set in Mediterranean blue and sandals that can handle craggy coastlines with ease.

ALEMAIS SHIRT, goop, $465;
ALEMAIS PANTS, goop, $425
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St. Agni
Top
goop, $128
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Alemais
Pants
goop, $425
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Alemais
Shirt
goop, $465
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St. Agni
Bottoms
goop, $120
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Natalie martin
Top
goop, $183
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EMME PARSONS
Sandals
goop, $425
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HEREU
Bag
goop, $590
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Natalie Martin
Shorts
goop, $83
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NATALIE MARTIN TOP, goop, $183
THE THEME IS: NEON
Not just for ravers and paint parties, neon has proven it can hang in grown-up settings, too. Don’t believe us? Lee Mathews’s sexy silk fuchsia set strikes a balance between fun and sophisticated, and BONDI BORN’s lime-green look is coolly minimalist. Both are good options for a birthday dinner or bachelorette party.

LEE MATHEWS CAMI, goop, $280;
LEE MATHEWS SKIRT, goop, $360
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Lee mathews
Cami
goop, $280
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A EMERY
Sandals
goop, $180
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Bondeye jewelry
Studs
goop, $950
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LEE MATHEWS
Skirt
goop, $360
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BONDI BORN
Top
goop, $245
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MANSUR GAVRIEL
Clutch
goop, $595
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Sapir Bachar
Necklace
goop, $414
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BONDI BORN
Skirt
goop, $495
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BONDI BORN TOP, goop, $245;
BONDI BORN SKIRT, goop, $495
LOVE IS IN THE AIR
Weddings, engagement parties, commitment ceremonies—they’re all an excuse to go big on romance. We’re talking bows, ruffles, big sleeves—the whole nine. Kika Vargas’s dark-blue taffeta set is sweet but not saccharine (especially styled with strappy red heels) and Cara Cara’s blue china-like florals are appropriately festive, particularly with those sapphire drop studs.

KIKA VARGAS TOP, goop, $552
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Kika Vargas
Top
goop, $552
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Neous
Sandals
goop, $590
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Sapir Bachar
Earrings
goop, $256
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Kika Vargas
Bottoms
goop, $392
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Cara cara
Top
goop, $325
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Hereu
Bag
goop, $520
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Sorellina
Studs
goop, $1,250
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Cara Cara
Skirt
goop, $395
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CARA CARA TOP, goop, $325;
CARA CARA SKIRT, goop, $395
YOU MEAN BUSINESS
Show up to work in a chic monochrome look and conquering the day—or even just your inbox—feels infinitely more rewarding. Finish with contrasting accessories that suit the warmer weather but still feel office-appropriate, like croc-embossed sandals and the suede Neous bag that our stylists are obsessed with.

PROENZA SCHOULER WHITE LABEL CARDIGAN, goop, $495;
PROENZA SCHOULER SKIRT, goop, $395
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Proenza schouler White label
Cardigan
goop, $495
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A Emery
Sandals
goop, $190
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NEOUS
Bag
goop, $870
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Proenza schouler white label
Skirt
goop, $395
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Lee Mathews
Tank
goop, $410
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Emme Parsons
Sandals
goop, $395
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Aesther Ekme
Bag
goop, $495
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Lee Mathews
Pants
goop, $550
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LEE MATHEWS TANK, goop, $410;
LEE MATHEWS PANTS, goop, $550
YOU’RE FEELING NOSTALGIC
Go full-on gamine (à la Audrey Hepburn) in a dark-navy set, ankle-strap sandals, and a sunny bucket bag. Or appeal to your inner flower child with a ruffle-sleeve crop top and long, grass-skimming skirt done in soothing tones of sage and honey.

CIAO LUCIA JACKET, goop, $365;
CIAO LUCIA PANTS, goop, $320
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CIAO LUCIA
Jacket
goop, $365
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Aeyde
Sandals
goop, $275
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HEREU
Bag
goop, $445
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CIAO LUCIA
Pants
goop, $320
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Mirth
Top
goop, $178
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TOTEME
Sandals
goop, $490
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ARIEL GORDON
Necklace
goop, $695
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MIRTH
Skirt
goop, $268
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MIRTH TOP, goop, $178;
MIRTH SKIRT, goop, $268
THE MOTIVATION HITS
This lavender workout set from HÉROS is perfect for gentle and low-impact workouts, like yoga or mat Pilates, while The Upside’s sweat-wicking rainbow-trimmed pieces are prime for more-intense activities, like running, boxing, or an early-morning Barry’s class.

HÉROS CROP, goop, $95;
HÉROS LEGGINGS, goop, $110
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HÉROS
Crop
goop, $95
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Birkenstock
Clogs
goop, $158
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Bala
Power Ring
goop, $89
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HÉROS
Leggings
goop, $110
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The upside
Bra
goop, $90
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ADIDAS BY STELLA MCCARTNEY
Jacket
goop, $230
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CW&T
Jump Rope
goop, $85
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The Upside
Pants
goop, $120
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THE UPSIDE BRA, goop, $90;
THE UPSIDE PANTS, goop, $120
YOU’RE OFF THE CLOCK
For some people, Saturday is for winding down, chilling out, and maybe curling up with a book. For others, it’s a chance to catch up with people they didn’t get to see during the week. But whichever camp you’re in: A sundress is the ultimate weekend uniform.
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Mirth
Dress
goop, $325
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Matteau
Minidress
goop, $480
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SEA
Dress
goop, $425
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Natalie Martin
Maxidress
goop, $383
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Natalie Martin
Dress
goop, $420
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Natalie Martin
Dress
goop, $315
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