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.

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).

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.

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.

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.

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.

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