We’ve covered how to make a fortune, how to manage (or fire) your boss, what it means to work smarter, and many other career topics. And now, it’s finally time to discuss the perennial and important work-related question: How should you dress?
That usually means dressing professionally, the way most successful people in your organization and industry dress — those people whose jobs and reputations you eventually want.
Now, especially early in your career, it’s easy to resent that.
For example, you might feel that your personal clothes are part of your identity and that having to dress differently at work is an affront to who you are. Or you might be confused about what it means to dress professionally.
Also, “professional” clothes can be expensive and a pain to care for.
And sometimes they’re uncomfortable.
I sympathize — because I used to think that way!
When left to my own devices, I dress extremely casually. For example, thanks to a moth invasion, most of my sweaters look like they were used as targets at a shooting gallery. But when I’m home, I still wear them. Because they work. Also, from April to October, when it’s hot and humid in the northeast, I usually wear shorts. Because they’re comfortable.
(My editor, Hayley Peterson, once wrote a story about “short suits” — a short-lived fashion trend that tried to blend suits with shorts. Fortunately, I never read it. Because I might have tried it. And then I would have looked even more ridiculous.)
Anyway, at the beginning of my career, my desire to “just be me”—and my hatred of formal clothing—actually factored into the kind of work I chose to do. (Freelance writing, teaching tennis, etc.)
Even today, I have to remind myself that the clothes that I reach for instinctively at home are not suitable for work — including Zooms.
But I no longer resent society or my employers or colleagues for making me dress up a bit.
This is because I now see that, whether or not it should, appearance and professionalism in the workplace (including clothing) affect how you’re perceived — and, therefore, can impact career progression and, in some cases, the quality of your work. (I’ll come back to this.)
I also see — and this is key — that it’s not about me.
It’s about respecting my colleagues and job enough to make an effort to look and act professionally and represent my organization in a way that helps it.
No, you don’t necessarily have to wear suits
Importantly, “dressing for success” does not mean always wearing a high-end suit. In fact, in today’s workplaces, that would rarely be appropriate — and could even be considered bizarre, ostentatious, or stuffy.
It also doesn’t mean you have to look “sharp” or “stylish.” (No one will ever accuse me of that!)
“Dressing for success” just means looking professional and in keeping with your workplace culture — as opposed to how you might dress on the weekend or at home.
In some workplaces, that means suits.
In others, it means “business casual.”
In others, it’s “anything but pajamas or bathing suits.”
In others, (it seems), it’s almost anything.
It also, of course, matters what kind of work you do. If you’re an individual contributor like a software developer or writer, where you rarely interact with colleagues in person or on video and never physically represent your employer to the outside world, your clothes are less important. Your boss may care what you’re wearing, so it will behoove you to know that and make an effort. But the less you visually interact with people, the less it matters.
In these cases, moreover, you can argue credibly that you do your best work when you are most comfortable and, therefore, that it’s in your employer’s interest to define “dressing for success” as “dressing in the way you do your best work.”
(Though, even here, it’s worth pointing out that some individual contributors — like the biographer Robert Caro — wear a suit and tie every day even when they sit alone in their office and never interact with anyone. Why? In Caro’s case, he’s said it reminds him that he’s a professional who has a job to do, and is at work.)
When you do visually interact with people at work, moreover — internally or externally — your clothes and general appearance make a much bigger difference.
This is because, for better or worse, and whether they should or not, humans form impressions about each other at a glance. These impressions are based on facial and behavioral cues as well as… clothes.
Not surprisingly, research suggests that looking more professional creates a better first impression.
(It also suggests that shelling out to buy a bespoke suit vs. an off-the-rack one pays off. So apparently, in the days when I worked on Wall Street and wore suits, I should have done that!)
Once your bosses, colleagues, and outsiders have formed an impression of you as a competent and respectful professional and an asset to your organization, you have more latitude. In that case, joining a weekend or evening Zoom in your gym clothes will be understood as a situational-specific convenience, not a benchmark of your professionalism and attitude.
But if you always dress in gym clothes, pajamas, or cut-offs, even when meeting in person with colleagues, clients, prospective clients, outsiders, and people who work for you, many of these folks may assume that you care little about your work and job.
These people might further assume that, if you don’t care enough to look professional, you also probably don’t care enough to behave professionally in other ways that could affect the quality of work you do.
That impression could hurt not only you and your employer and your career prospects, but your ability to do your job.
Remember:
As with other aspects of professional conduct, dressing for success is not about you. It’s about your respect for the organization that is paying you and the colleagues you work with. And it makes a difference.
