So You’re Going out Again. Do You Remember How to Dress?

Christina Binkley On Venturing Back To Work Meetings

I regard my pandemic wardrobe—the American Giant sweatpants with the ripped knee, the rotation of black Everlane T-shirts—with the same affection I had for maternity clothes after giving birth. As in, no affection whatsoever. Those lockdown cocoons served in a time of need, when a challenging fashion decision was between donning a fresh crew neck or continuing the day in yesterday’s slept-in V-neck. I’m moving on now, more focused on comfort and, let’s face it, several pounds heavier.

My calendar is suddenly filled with in-person work meetings, carefully scheduled at outdoor restaurants, and get-togethers with friends I haven’t seen in over a year. These fully vaccinated people will find me wearing a loose new wardrobe, shopped for at my desk during the long months of 2020, a year that seems to have occurred a decade ago. This new wardrobe isn’t extensive, so I will repeat it often and with abandon. It has elements of a uniform because when I discovered Maria Cornejo’s canvas bias-cut slacks, I bought a second pair in denim and then did the same with a silk gathered-neck blouse, also by Ms. Cornejo, which I now own in two colors. I bought a raft of scarves by Anokhi, whose Indian block-printed blouses and tunics I discovered a decade ago at Simrane, a little shop on Rue Bonaparte in Paris, then happily rediscovered this year online. I did buy a tailored blazer from the Row that is so minimal you won’t know you saw it three times last week.

A few days ago, I had a meeting with a longtime associate from out of town and her London-based colleague, whom I’d never met. I frankly gave little thought to clothes—just tossed on Ms. Cornejo’s denim slacks and the orange gathered-neck blouse, and stuck my un-pedicured feet into suede Birkenstocks that look faintly Japanese. I gave a great deal of forethought, however, to how we would greet: Cheek kisses must be completely pre-pandemic, right? Are hugs allowed before we reach President Biden’s 70% vaccination threshold? We were taking care to meet in the fresh air at the Alcove in Los Angeles, where the seating is entirely out of doors, but what about handshakes before food?

If the pandemic has taught us anything other than the value of good ventilation, it’s that societal norms can be rejected, reformed, rejiggered faster and more easily than we ever imagined. After a lifetime of dressing to be appropriate—keeping heels in my desk at the office, cinching my belt for a night out—I am dressing for myself now. I may come across as quirky, possibly inexcusably wrinkled, but perhaps I’ve finally discovered in middle age what personal style really is.

So I will miss Vanessa, my colorist of a dozen years, whose kids are roughly the same age as mine. My hair was last dyed in April 2020 when she dropped a kit by my house. Fourteen months then passed in a blur without manicures or teeth cleanings, and now my salt-n-pepper locks match how I feel—respectable enough to be called ma’am by waiters at good restaurants.

My new look didn’t come up in my meeting at the Alcove. We shook hands without sanitizing. We hugged—a great big one. And I noticed fleetingly that my acquaintance, years younger than I, is letting her bits of gray show, too.

—Christina Binkley is a writer and former reporter at The Wall Street Journal.

Wilbert L. Cooper On Dressing for New, Potentially Embarrassing Hobbies

For most of my adult life, I’ve tried to use my clothes to project an aura of success, no matter how impractical or ridiculous the garments were. I once wore a blacked-out, big-booted Rick Owens look to the sunny shores of Miami Beach because I was far more concerned with snapping cool photos of my outfit than I was with actually having fun in the sun.

But then the pandemic happened. All of that pain, death and loss forced me to reckon with how uncertain the future is and how fleeting joyous moments can be. I thought about all the times I went to the club in extreme, pointy-toe ankle boots that I couldn’t dance in, or the days I took my nephew to the park in designer clothes that I couldn’t afford to get dirty. And I had to ask myself: Why spend so much time and money on crafting an image for yourself if that image gets in the way of having a good time?

That question popped back into my mind recently when I received one of my first post-lockdown invitations. A friend of mine was celebrating her birthday at Skate Country Westbank in Gretna, La. The party was happening during “adult night,” when the really skilled skaters of all ages hit the wood in Instagram-ready looks—brothers come with dip-dyed high-top locs and gold chains, the ladies turn up with door-knocking earrings and hot pants. And these folks don’t just lackadaisically roll around the rink. They boogie their bodies to the thunderous sound of bounce music while looking good. To say it’s a stylish scene would be an understatement. And before the pandemic and its many months of uncertain isolation, I would have spent too much time perfecting a flashy look of my own—forgetting the fact that I was there to celebrate my friend’s birthday, or that I haven’t laced up a pair of roller skates in about two decades.

Instead of picking out some gear that would grab the most attention, I attempted to put together an outfit that would actually allow me to enjoy being at the rink. I rocked some wide-legged track pants from Italian designer Stefano Pilati’s brand Random Identities that would easily fit over roller skates and had a lot of give, so I wouldn’t have to worry about any embarrassing split seams if I fell down. And I paired those with an oversize, honey-colored camp shirt to give myself a free range of motion while gliding across the floor. My outfit also projected a breezy, laid-back vibe that was perfect for relaxing while cooling off after a few brisk runs around the rink.

Whether we’re talking about my look or my wheel skills, I definitely was not the prettiest skater on the floor. There were bad boys skating backward in trendy bucket hats and ladies confidently doing line dances in the middle of the rink. However, as I propelled myself forward underneath the candy-colored disco lights, my relatively practical clothes billowing around me, I felt alive for the first time in a long time.

—Wilbert L. Cooper is a writer and an editor.

Jacob Gallagher on Suiting up for His Nuptials

My fiancée, Rachel, and I had slated our wedding for August 2020. We always planned for it to be small: our families at a local restaurant. But then Covid hit, and we tentatively postponed to August of this year. In April, when New York’s vaccine program widened, it became clear that our wedding really was going to happen.

We were caught flat-footed. During Covid most of the details of our wedding—rings, flowers and, oh yeah, what we were going to wear—had fallen by the wayside. For a week or so, I thought I’d wear a solid navy suit that I’ve had for years, but when I took it out, it didn’t feel special. It was a ho-hum suit I’d worn to a relative’s bar mitzvah. It wasn’t gonna cut it.

All weddings are festive, but ours will double as a celebratory family reunion. This happy occasion calls for a jolly suit, and I resolved that I should wear green—a color that’s buoyant and, some say, lucky. But I didn’t want to look like I belonged on a can of spinach. I envisioned a suit in dark green—more like an avocado’s rind than its insides.

Turns out, suits in this hue are elusive. The one I located, a forest-y, double-breasted option from London label Drake’s, fit me horrifically—the jacket was too long, the pants too tapered. I realized I’d have to go custom and visited P Johnson, an Australian tailor with an outpost in New York who favors modern coats and breezy fabrics.

Still, my options in green were limited. One fabric was thick enough that I’d be flop-sweating at the altar. Another muddied material gave off swamp-water vibes. Fortunately, the final fabric was ideal: a gauzy “tropical wool” weave in a savory hunter green. The issue was the price—this was one costly textile. The suit came to $2,400, which blew my $1,500-ish budget. I’ve never spent so much on a clothing item before. It’s nearly half of what I paid for my car.

But, as is often the case with weddings, I lost my good sense to fantasy. The fabric was sublime. I gulped and pushed ahead, though I decided to make the suit a bit more casual so I could get the most out of my investment. I opted for informal patch pockets instead of stuffy flap pockets. I also made the trousers pleated and wide, so they draped freely. The suit was proper enough to pair with a tie at the wedding, but also casual enough that I’d feel OK putting it on with a T-shirt to meet a friend for dinner. At least, that’s what I’m telling myself each time I check my credit card balance.

—Jacob Gallagher is the men’s fashion editor at Off Duty.

Katharine K. Zarrella on Not Frightening Babies

I generally dress like the love child of Maleficent and a beefsteak tomato. It’s a look I maintained during lockdown, though I swapped my usual sculpted skirts and leather jackets for red and onyx tulle dresses and vintage kimonos.

Arming myself in idiosyncratic outfits, I’ve found, conjures confidence and energy. And studying strangers’ reactions—from thumbs-ups and emphatic nods to eye rolls and scoffs—is endlessly amusing. Isolation hit pause on that diversion, so I now use any outing—a CVS run, dinner with Dad—as an excuse to dress wildly.

When Meg, one of my best friends, invited me to her daughter’s first-birthday bash, I was touched. The prospect of concocting a look for an actual party thrilled me. It also made me anxious: My outré clothes have often inspired the under-7 set to hide behind their parents or ask if I’m a witch. My default reply: “Yes, but a good witch. Mostly.” I don’t mind if Meg’s daughter finds me witchy (can babies discern witchiness?). But I don’t want to pay for her therapy.

How my wardrobe might affect a child’s psyche was not something I considered in lockdown. Frankly, as a single 35-year-old whose only charge is a black pet rabbit, it’s not something I’d considered ever. But the pandemic moved many of my pals to fast-track their family plans. One was wed in a live-streamed ceremony and moved across the country. Another had her second baby. Meg, who lived mere blocks from me for years, decamped to Long Island last August after giving birth to her first child.

Planning this outfit illuminated how much has changed since March of 2020. It made me wonder how—or if—I fit into my friends’ new lives. I’m exceedingly happy for them and these chapters would have opened regardless of Covid. But when it all unfurls in quarantine and suddenly you’re smacked with an unfamiliar reality, it’s jarring.

While I pondered this existential crisis and gazed into the black hole that is my closet, one piece beamed like a sartorial north star: a stiff “paper doll” dress from Comme des Garçons’ fall 2012 collection. It’s black, flat, juts out a foot on each side and blooms with an overblown red-and-pink rose print. Paper dolls and flowers aren’t scary—they’re delightful! I’ll pair it with a shocking pink turban, polka-dot heels and bulbous baubles that a baby will enjoy grabbing but can’t choke on or destroy. It’s authentically me, but it won’t make children cry. I hope.

—Katharine K. Zarrella is the fashion editor at Off Duty.

Jason Gay on Tying the Knot

Critical breaking news: I intend to wear a necktie this month. I’ve been asked to attend a graduation ceremony, and unfortunately it’s not the type of occasion where I can just wander over in a gray hooded sweatshirt and Yoda pajama bottoms. I might actually meet people, respectable people, in person. After 15 months sequestered, I need to worry about making a proper first impression. Yes: It’s deeply terrifying. I’m as worried as you.

There was a time when I’d wear a necktie several times a week. That time coincides with an era when people ordered DVDs to be delivered by mail. During the pandemic, my tie-wearing dwindled from occasionally to never. I’m rusty. I don’t remember the moves. I know there’s the Windsor knot, and the half-Windsor, but that’s it. Please don’t ask me how to tie a bow tie. There was a time I knew how, but today, that’s like asking me to land a commercial jet.

To be clear: I’m pro-tie. I think they’re spiffy. I think a good, crisp tie conveys classiness and cool, for men and women; you can’t tell me that Diane Keaton hasn’t worn ties just as stylishly as Cary Grant. A great tie is versatile, able to adapt to the moment and the mood: tightly knotted when it’s daytime business; slightly loosened if you’re off the clock; completely undone if you’re out with the Rat Pack and trying to find a joint still serving at 5AM.

I used to own many ties, including silky, pinstripe ones that made me feel like an industrialist; knit ties that made me feel like a budding novelist; skinny ties that made me feel like the trombone player in a ska band. If you’re in a suit, a tie completes the look. The designer Tom Ford says that wearing a suit is like wearing a confident coat of armor; if that’s true, then a tie is the sword. This is why you should never wear a silly fish tie. Imagine going into battle holding a fish.

I’ve got a few ties left in the closet, and the other day I grabbed one and stood in front of the mirror. Miraculously, it came back to me: a familiar, natural impulse, like riding a bicycle, or complaining when my pizza is late. I won’t lie: it looked pretty good, right on the first try. I have no idea if the knot was a Windsor or a half-Windsor. I’m not Diane Keaton or Cary Grant. I’m just some laptop stooge who’s got to wear a necktie for the first time in a long time. I feel like an astronaut, putting on a helmet to rocket to the moon. Wish me luck.

—Jason Gay is a sports columnist and humor columnist for The Wall Street Journal.