Don't Be Dressed To Fail: Why What You Wear Determines Your Success

Over the course of the past summer, I started noticing a certain woman in my totally unhip Queens, NY neighborhood. Given her sense of welp, “style,” it would have been difficult not to notice her. I’d generally see her, on my morning run, at around 6:30 or 7:00 am, walking to the subway in various versions of an ensemble that tended towards bright, skin-tight maxi dresses, Pepto-Bismol pink wedge flip-flops and talon-like nails, painted a subtle neon hue.

It got to the point, that whenever I saw this woman, I found myself thinking, “Oh, that poor girl! Why do they keep giving her the morning shift at the strip-club?” While I have no proof that she works as a stripper. (And, let’s face it, in light of the brain trust in Washington, D.C., our national economy is basically being maintained by strippers and the people who love throwing dollar bills at them.) But given this woman’s sartorial choices, I assure you she’s not working in any office, I’d ever want to visit. Unless by “visit,” you mean, watching it get raided by the Feds during an episode of “Manhunters: Fugitive Task Force.”

At my job I help people reinvent themselves and create professional opportunities. A great deal of my coaching consists of helping people not sabotage their careers. I noticed this woman because when I see someone dressed like that on a Tuesday morning, I know they are not allowing themselves to succeed. I’m picking on this woman because she’s really an extreme example of what I see in my business all the time: people, women especially, who are actively destroying their professional opportunities by how they dress.

I’m talking about people who dress in a manner that seems to announce to the world that no, they don’t believe they deserve to move up the ladder, they’ll take whatever crap they’re given and hey, what’s so wrong with getting dressed in the dark…during a fire? Does this seem superficial? Allow me to welcome you to corporate America.

Think of your office not as a beauty contest, but as a branding contest. When you go to work, you are on public display. You are being considered for upper management roles. You’re constantly being evaluated as to how well, or how badly, you personally promote the company’s brand. Some of your contribution is solely based on how you look and behave.

Your management is considering whether or not they can send you on trips, to conferences, whether or not you will represent your company as a powerful, attractive brand. Management is considering what message you convey. So, when you routinely show up for work, looking like you were just fired from Buckwild, when you look like three walks of shame gone bad…you hear that sound?

That’s the sound of your career giving up. When I visit clients in their cubicles, and they look like they were forced to dress at gunpoint, and then these very same clients have the audacity to say to me, “Yeah, Carlota, somehow, I don’t know, I can’t seem to get promoted?” That’s when I have to remind myself that murder is technically illegal. Even mercy killings are frowned upon.

Before you roll your eyes into next week, I assure you that I hold myself to these same standards. I have to: I’m self-employed. Now it is true that on the days I don’t have clients scheduled, I usually wear sweats, mascara and cat-hair. But when I have client sessions, I dress up. People are giving me their money and trust; I’m not going to blow it by showing up in yoga pants and a YOLO t-shirt. People tend to be highly skeptical regarding the virtue of any “valuable” advice given by someone wearing clothing that espouses the YOLO methodology.

That’s the point of dressing professionally: you’re demonstrating that you know what you’re doing. You’re announcing that yes; you are worthy of your management’s confidence, attention and resources. You need this to create an exciting, long-term career. When you dress in a professional manner, which enables you to blend into your corporate culture, you’re demonstrating that you understand and value that culture. Do you really think someone who obviously doesn’t value their company’s culture is going to be seen as valuable to that company? Being well dressed is also an excellent way to bolster your own confidence and realize that yes; you can do this job and deserve this opportunity.

Can this be a huge pain in the ass? Yes. Does this mean that you might have to set aside time on the weekend to do your laundry, pick up the dry-cleaning and organize outfits for the week, so that your morning exhaustion won’t sabotage you, by justifying dirty jeans on a Wednesday, when the CEO walks by your office and is appalled? You bet. Does it also mean that you should note what your superiors are wearing, and create your own version? Yep.
Ask yourself: “How far do I want to go in life? How hungry am I? How much positive attention do I want?”

We’re all animals who operate within the rules of biology; people tend to give attention (i.e. opportunities) to people they’re attracted to. If you dress like you don’t matter, how can you expect your boss to think that you do? Once those opportunities are rescinded, they usually don’t ever return. Finally, work is not the place to experiment with clothing. Nor is any part of the NYC subway system. The correct place to experiment is your bedroom, when you’re 15 and the world truly revolves around you. Work is the place to be appropriate! As in, appropriate to your industry, your company and your position.

You need to dress in a manner that indicates that yes, you should be trusted to represent your company’s brand in front of strangers. Because, and this is crucial, if you look bad, you make your company look bad. And guess what happens when you make your company look bad? Whomp whomp. You have to take ownership of your career so you can dress and behave as if your time and contribution are vitally important. And aren’t they? Aren’t you valuable? Remember that while it may seem like a large daily effort, but great careers don’t just happen. People create them through drive, determination and dressing for the success they demand.

Top photo courtesy of USA Network