How Men Should Dress for a First Date in 2021

AFTER A YEAR in my condo, I’ve modified my thoughts on a few issues,” mentioned Matthew Kehoe, 42, “one of which is dating attire.” Mr. Kehoe, a movie producer in New York, is among the many many single males re-entering the in-person relationship sport after months of relative isolation. But simply as work, journey and socializing have advanced unpredictably since February of 2020, so too has the hunt for a mate. That’s not essentially a unhealthy factor.

For starters, as males emerge from their quarantine caves into a wobbly world, splashy suit-and-tie formality now not feels acceptable. “Now may not be the time to show off your brightest custom blazer or loudest Robert Graham print,” mentioned Tammy Shaklee, a licensed matchmaker and the founding father of H4M Matchmaking. Ms. Shaklee finds casual dressing for dates refreshing and extra “comfortable for a more subdued, face-to-face, getting-to-know-you type introduction.” In different phrases, after what we’ve been via, let’s be light with one another and keep away from the sartorial pomp so prevalent in pre-pandemic relationship.

That mentioned, extra relaxed attire doesn’t imply relationship itself has grow to be any simpler. The stakes are increased than ever. “I’m much more selective now,” mentioned Mr. Kehoe. “I go on way fewer dates and they’re more important. When you think the world might end…you don’t want to go on a random date.” Imminent apocalypse apart, whether or not you’re a 20-something taking part in the sector or a romance veteran getting again on the market after a silver divorce, you’re re-entering the relationship market similtaneously a lot of aggressive males. If you may’t beat them in phrases of internet value or appears, you’ll need to beat them with appeal—and in the menswear area. Here, 5 dating-style ideas from specialists and single guys. And earlier than you ask: Yes, you do must put on pants.

Be Yourself, Casually

These days, gratuitous formality feels stuffy, affected and out of contact. “It’s more about being comfortable,” mentioned Mr. Kehoe, referring to his post-lockdown relationship attire. He believes that, when dressing for a date, it is best to put “your best foot forward,” however not project a disingenuous distortion of your actual self. Before Covid, he would layer on a modern first-date veneer, carrying tucked-in button downs, Hermès belts and Gucci loafers. But that status-conscious technique feels phony now that he spends most days in Converse sneakers, Levi’s and Grateful Dead T-shirts. “At the end of the day, they like you or they don’t, so why wear something you don’t [normally] wear?” Lately, Mr. Kehoe has adopted a relationship uniform of denims and T-shirts. He contends the just-laid-back-enough look establishes an unpretentious tone that’s “appreciated on the other side.”

Good Jeans Never Fail You

Wool trousers, stiff khakis and something harking back to pre-pandemic office attire are solidly out. Jeans, nonetheless, have by no means been extra apropos. A thought-about pair telegraphs that you considered your first-date look—however didn’t overthink it. The flawed pair, nonetheless, might encourage your date to flee via a toilet window susceptible to shredding her personal outfit. Though advising on a wash is difficult, keep away from something overwrought or Twisted Sister-ish. Really give attention to match, mentioned Greta Tufvesson, co-founder of bespoke matchmaking service the Bevy, which serves shoppers in New York, Los Angeles and San Francisco. “I don’t think a man should wear a baggy, long jean. It should be fitted around his legs and tailored to his correct inseam.” Ms. Tufvesson, who additionally approves of a rolled cuff, advises her shoppers to staff their denim with a good T-shirt (she champions navy Breton stripes this time of year) and toss a softly tailor-made jacket over the ensemble for a dressier look.

Back to top button