Does Dressing for Success Really Work?
Working remotely comes with a wealth of perks—bosslessness, flexible hours, the ability to work from this Dunkin’ Donuts—but none is better than the dress code.
For six 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 several newspapers. (If you’ve never been, newsroom dress codes range all the way from Deeply Casual to Basically Homeless.)
Related: The Truth About Working From Home
Of course not all freelance writers dress this way. Gay Talese, the pioneering literary journalist, told 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.” He claimed to own more than 100 tailored suits and at least that many fedoras.
In most places outside of Wall Street and Capitol Hill, though, dress codes are loosening up. That said, we still live in a world of impressions, first and otherwise. And for better or worse, those impressions come visually and often from clothes. If I’m in a lobby waiting for an interview in my bestest Vans, and the other guy is in a slick suit and tie, I’ve damaged myself. I might be sharper and more talented, and might 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.”
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, at least 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 important—my impression of myself.
On the first day, 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. 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 do. I am a professional.
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.
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 and 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 am here regularly—surely the staff and teachers here would notice that something is different, that my formality is 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 sums up the week pretty well.
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.