Working remotely comes with a wealth of perks—potentially increased happiness, flexible hours and the ability to work from Dunkin’ among them. But none is better than the dress code.
For years, the ensemble I uproariously call my “work uniform” has been standard Writer Guy: potentially clean jeans, button-up shirt over a probable graphic tee and Vans sneakers. It’s always felt professional to me, perhaps because prior to my freelance life, I worked at newspapers including Hilton Head Monthly. (If you’ve never been, newsroom dress codes can range all the way from dressy to deeply casual.)
Of course not all freelance writers dress this way. Gay Talese, the pioneering literary journalist, wrote in Vanity Fair in 2007 that “putting on a beautifully designed suit elevates my spirit, extols my sense of self and helps define me as a man to whom details matter.”
For white-collar workers, however, dress codes may be loosening up. That said, we still live in a world of impressions, first and otherwise. If I’m in a lobby waiting for an interview in my best Vans and the other guy is in a slick suit and tie, I’ve damaged myself. I might be sharper and more talented, and may very well get the job, but I’ll have to dig out of a hole to do it.
“Perception is everything. There is no reality,” says Caroline Dowd-Higgins, executive director of career and professional development at the Indiana University Alumni Association. “If I come to work in yoga pants, the perception might be that I’m laid-back and casual, so maybe my work ethic is, too. I want to be able to set a tone, establish myself as a promotable player.”
Dressing for success for a week: an experiment
Frankly, I have little experience in this field. So I set out to see whether the clothes made the man by donning a suit daily—dressing for success for a workweek. I’d wear it to my usual travels: kindergarten drop-off, the coffee shop where I work, dentist appointments, the pizza place where I take my sons on Tuesdays, my standing lunch with my buddy Bradshaw. The idea was to gauge the effects of the visual, to see how a suit affected other people’s impressions of me and—more importantly—my impression of myself.
The initial confidence boost
On the first day of dressing for success, at 8 a.m. in the kitchen, my wife asked, “What in the world are you wearing?” A good start.
An hour later, I opened the door to my usual caffeinated workplace with a noticeably increased sense of swagger, a confidence that had been absent from my previous 14,000 morning visits. But disappointingly, nobody seemed to give the slightest notice to my amplified handsomeness. Not the baristas. Not the other regulars. And not the personable veteran who runs the place.
“But look,” I self-consciously tried to broadcast, ambling slowly to the croissant rack, “I am properly and handsomely attired for the day’s travails! I am a professional! I hath matched mine socks to mine own pants!” I did this for an hour. Nothing happened, except for somebody asking whether I wanted whipped cream on my salted caramel mocha. Of course I did. I was a professional.
Feeling like George Clooney
On Day 2, I left for work at the same time as my suburban neighbor, both of us climbing into our sensible family-toting small SUVs while waving collegially to each other. We were headed out to carpe the diem, to grab the world by the throat, to make our mark.
My kindergartener forgot his backpack that morning, meaning I had to return home, retrieve it and bring it back to his school’s office. “Hi, guys,” I said brightly, entering the school in a reasonable approximation of George Clooney walking into the Bellagio in Ocean’s Eleven. “I have a backpack.”
“I can see that,” replied the nice lady at the desk. “It matches your suit.” It was an R2-D2 backpack, so she might have been insulting me, but at least someone noticed.
Dressing for success and feeling out of place
On Day 3, after waving again to my increasingly weirded-out neighbor, I drove downtown to one of our city’s finest hipster establishments, a coffee shop thick with Ramones music, blue-haired baristas and posters for art riots and kombucha. In this space, looking outlandishly formal, I felt less like I was settling in to write and more like I was about to issue citations about health-code violations.
Later that day, I opened the door to my son’s after-school care with expectations high. I was there regularly—surely the staff and teachers here would notice that something was different, that my formality was worth bringing up! And yet, nothing. Zero.
The next day I wore the suit to Target. Maybe I was just being self-conscious, but it really felt like most of the other people in the LEGO aisle were looking at me funny.
On the morning of the last day, my 13-year-old son asked, “So how long are you going to play dress-up?” That summed up the week pretty well.
Dressing for success for a week: the results
I realized my wiseapple eighth-grader was right. That was the effect. I felt overdressed. For everything.
My world is simply not one that demands formality; if anything, it does the opposite. Wearing a suit felt alien to my travels and tasks, some sort of plea for attention. It was nice to enjoy the subtle respect afforded to people who look put together, on the rare occasions when that happened, but mostly it felt silly. And none of these people knew me. My family knew I was up to something, but to everyone else, I was just another guy in a suit.
The problem, I learned, was that I wasn’t matched for my day, my needs, my audience. If you work in an open floor-plan loft that is essentially a pinball-powered juice bar where millennials occasionally build apps, bring it down. If you’re a lawyer, don’t show up to work in a Pearl Jam T-shirt and cargo shorts, or there will be words. The simple solution is to respect the situation.
I’ve spent a considerable and accidental amount of time cultivating my personal brand, which remains an irritating way to say, “Be what you are already.” People generally know what to expect from me as a freelance magazine writer. When I present myself in a way that’s contrary to that image, it throws things off and makes people feel out of place, uncomfortable. Especially me.
But I looked fantastic.
This article was updated April 2023. Photo by Gutesa/Shutterstock
