What to Wear on a First Date according to Professional Matchmakers – Amanda Chung

Photo courtesy of Emily Wells

What to Wear on a First Date according
to Professional Matchmakers

Now that first dates don’t have to be over FaceTime, we turned to two experts—Greta Tufvesson and Nikki Lewis, founders of The Bevy, a boutique matchmaking service—to shed light on what to wear and how the dating scene has changed. “We’ve noticed a shift for the better,” says Lewis. “COVID has made us all reprioritize what really matters in life, and there’s an open-mindedness around the entire sphere of meeting someone.” With that in mind, we pulled together six fun first-date ideas and what to wear for each.

Laid-Back Stroll

Keep things easy with a breezy cotton-linen sundress, sunglasses, and an unfussy crossbody that fits just the basics. “Still do your makeup, but try a natural, less-is-more approach,” Lewis suggests. ILIA’s new tinted serum brightens and protects skin with SPF 40—and it’s so lightweight, you’ll forget you’re wearing it.

Wolf Circus
bracelet
goop, $90
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ILIA
face serum
goop, $64
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G. Label
Kemp Striped Skinny-Strap Dress
goop, $595
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Loewe
bag
Net-a-Porter, $550
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Ray-Ban
sunglasses
goop, $203
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Veja
sneakers
goop, $105
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Sporting Event

Bring your A-game with a flattering V-neck bodysuit and a striped roll-neck sweater that works just as well draped over your shoulders as it does cozied over true-blue, vintage-inspired jeans. And though it might sound like the ultimate mom-ism, Tufvesson says to wear comfortable shoes (these stark-white platform sneakers fit the bill).

Wolf Circus
bracelet
goop, $125
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Ami Colé
highlighter
goop, $22
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Maria McManus
Bodysuit
goop, $550
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G. Label
Baxter Chunky Striped Sweater
goop, $595
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AGOLDE
jeans
goop, $198
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Chloé
bag
Chloé, $2,390
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Common Projects
sneakers
Net-a-Porter, $440
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Sit-Down Dinner

“Dinner is not a drill—it’s a commitment of time and the ultimate audition, so don’t be afraid to take it up a notch,” says Tufvesson. This plissé satin dress is a pretty option, especially when paired with a red-leather clutch, a delicate cluster of diamonds at the ears, and a sumptuously soft cardigan. Since you’ll be seated, Tufvesson advises going all out on shoes.

Melissa Kaye
earrings
goop, $8,350
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Kosas
Lipstick
goop, $28
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Loro Piana
cardigan
Net-a-Porter, $1,575
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Ulla Johnson
dress
goop, $775
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Bottega Veneta
Clutch
Net-a-Porter, $2,100
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Bottega Veneta
heels
Net-a-Porter, $930
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Gallery Crawl

For a museum meet-cute, try a structured cotton-canvas shirtdress and a curated assortment of artful accessories, like a sage-green crossbody, the daintiest paperclip-chain anklet we’ve ever seen, and skinny-strap sandals.

Laura Lombardi
anklet
Farfetch, $80
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Kosas
lip oil
goop, $22
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Westman Atelier
highlighter
goop, $75
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G. Label
Pappen Puff-Sleeve Minidress
goop, $595
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DeMellier
Crossbody
goop, $465
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Jil Sander
sandals
SSENSE, $570
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Cocktail Hour

Dressing for a drinks date is all about balance, according to Tufvesson: “If you’re wearing a leggy skirt, try something less revealing on top. If you’re wearing jeans, pair them with a dressier blouse.” So yes, you can opt for that sexy zebra-print slip dress, but take a pared-back approach to accessories with sleek earrings, a swipe of inky mascara, and a simple bag.

Laura Lombardi
earrings
goop, $128
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Ami Colé
mascara
goop, $19
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Balmyard Beauty
lip + cheek tint
goop, $32
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TOVE
dress
goop, $810
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DeMellier
bag
goop, $425
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Femme
heels
Femme, $189
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Group Get-Together

Meeting at a mutual friends’ place for roast chicken and red wine requires a foolproof outfit. Like jeans that nip in at the waist and widen through the leg (for comfortable sitting, standing, etc.), a close-fitting cardigan that spotlights your dainty gold chain, and sandals that easily slip off in case your host runs a no-shoes household.

G. Label
deven link necklace
goop, $2,500
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G. Label
Fiene Yellow Gold and Pavé Ear Cuff
goop, $650
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Ami Colé
lip oil
goop, $20
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Gabriela Hearst
cardigan
Matchesfashion, $891
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AGOLDE
jeans
goop, $188
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The Row
purse
Nordstrom, $990
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Emme Parsons
sandals
goop, $395
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