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.
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.
Kemp Striped Skinny-Strap Dress
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).
Baxter Chunky Striped Sweater
“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.
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.
Pappen Puff-Sleeve Minidress
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.
lip + cheek tint
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.
deven link necklace
Fiene Yellow Gold and Pavé Ear Cuff
We hope you enjoy the products recommended here. Our goal is to suggest only things we love and think you might, as well. We also like transparency, so, full disclosure: We may collect a share of sales or other compensation if you purchase through the external links on this page.