IRL Dating Is Back. If You’re Ready for it, Here’s What to Wear

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It’s official; dating has recommenced. The era of socially distant dating is over. Goodbye to awkward and blister-inducing walks. Farewell to “meeting up” on a cringe-worthy FaceTime date where pretending to be frozen mid-sentence and then hanging up was never off the table. Rejoice in the IRL!

While hopping between favorite music-filled, dimly-lit spaces at full capacity is not yet in the cards, as vaccine rollouts continue, people are increasingly meeting up for coffees, drinks, and dinners. Dates are revving up—we’re hugging hello and, if things go well, we’re even kissing goodbye (what a concept!). But, navigating what to wear on a date, especially the first date in a post-pandemic world, can feel daunting. It’s not 2019 anymore, and tried-and-true outfits from dating’s past (read: sky-high heels) need to be tweaked to make sense for 2021.

While the ideal first date outfit is truly in the eye of the beholder, one thing is for certain: it has always been both polished and low-key—your clothes shouldn’t stand out more than you. In that vein, less is more, especially as we reemerge from a sweatpants-laden life. Going for a coffee date? Think jeans paired with elevated basics. Out for a drink? A knit top with careful cutouts or an open back paired with trousers and flat shoes will work swimmingly. Headed to dinner? Try a polished shirt that can be worn in a multitude of ways and contexts, no matter where the night takes you. Dress people, don’t fret—easy, longline dresses with non-fussy hemlines are a good bet, too.

There’s rarely a need to do an entire closet overhaul when prepping for a first date. On the contrary, getting ready for a first date is about nailing down your personalized first date formula—rinse and repeat. But you should also feel empowered to procure either a new dress or the perfect accessory to enhance your closet favorites. Here, shop polished shirts, no-fuss dresses, slinky knits, and updated takes on basics to help you get back out there dating again in no time.

Polished Shirts

On dating in 2021, Vogue’s Fashion and Style Writer Christian Allaire says, “I’d probably cancel the date out of anxiety and not go, but if I did go, I’d wear dark jeans and a fun printed shirt!” A good top goes a long way. Let a polished shirt amp up your favorite denim or trousers.

Gucci silk chiffon ruffle shirt

$1,700

GUCCI

Reformation Roe shirred silk-satin top

$168

NET-A-PORTER

H&M off-the-shoulder top

$25

H&M

Ciao Lucia Isla printed smocked cotton tank blouse

$295

MODA OPERANDI

Jacquemus ruched cotton-blend poplin shirt

$575

NET-A-PORTER

Christopher Esber cropped silk wrap top

$535

INTERMIX

Nanushka Tippi satin shirt in sage

$444$220
SMALLABLE

No-Fuss Dresses

Some of us are dress people and feel most ourselves in one. While super-short hemlines are having a bit of a moment, longer line dresses with non-fussy silhouettes are a carefree go-to for first dates.

Reformation Lauryl tie-front floral-print Ecovero-crepe midi dress

$148

NET-A-PORTER

Fleur du Mal halter neck slip dress

$445

FLEUR DU MAL

Alessandra Rich floral silk midi-dress

$1,770

MYTHERESA

Proenza Schouler White Label yarn-dyed plaid full-sleeve midi-dress

$495

BERGDORF GOODMAN

Zara dress with cutwork embroidery

$84

ZARA

Sleeper Belle shirred linen midi-dress and scarf set

$280

NET-A-PORTER

Elevated Basics

Whether you’re meeting up for coffee or a drink, investing in elevated takes on your favorite basics is a can’t-go-wrong way to dress for a date. Simple, minimal, and good.

Anna Quan Lena rib-knit sleeveless top

$210

FARFETCH

Mugler cutout ribbed-knit tank

$850

NET-A-PORTER

Helmut Lang cutout ruched ribbed cotton-jersey T-shirt

$185

NET-A-PORTER

Peter Do ribbed-knit top

$465

MODA OPERANDI

LaQuan Smith mockneck silk ribbed top

$395

SAKS FIFTH AVENUE

Gauge81 Beja one-shoulder knitted top

$270

NET-A-PORTER

The Line by K Ximeno open-back ribbed stretch-jersey top

$75

NET-A-PORTER

Slinky Knits

Second-skin dressing is a big trend for spring 2021. Opt for slinky knits with careful cutouts, open backs, and pretty necklines for a foolproof first date outfit idea.

Khaite Maddy ribbed-knit sweater

$1,080

NET-A-PORTER

Safiyaa Zaina cutout ribbed-knit fop

$805

MODA OPERANDI

Jacquemus Le Cardigan Tordu off-shoulder cardigan

$470

MYTHERESA

Magda Butrym cutout stretch-jersey blouse

$915

MODA OPERANDI

Jonathan Simkhai standard Janessa recycled cutout squareneck sweater

$175

SAKS FIFTH AVENUE