What Should You Wear To Work?

Last year, we implemented a dress code at the office.

(OK, I implemented a dress code at the office. Plural is probably not appropriate here.)

I implemented a dress code and it had some cool effects and every now and again I think about writing an article about it. Then I read this article about what entrepreneurs should wear to work – and of course, as we all know, you’re only an entrepreneur when you are under 30 and attempting to sell software in California – and I thought, you know? Perhaps now is the time.

Because dressing up has provided values I couldn’t have expected – and no, Dave going on way more dates is not what I’m referring to – I want to propose the same idea to you. Kind of like A Modest Proposal for the office, except not satirically.

What if you dressed like a grown-up for work?

Major decisions should not be based on rebellion once you are past the age of 14.

It was fashionable for a while, and maybe it still is, to put the word “pajama” in your business name to show the world exactly how indie you were. It didn’t start that way, I don’t think. I think it started as a way for mommy bloggers to differentiate themselves, and “pajama” served as a handy word anchor to show, “Um, I’m at home? Like, in my house? Not at a workplace?”

After a while, though, it became a rallying cry.

It wasn’t, “I work from home” anymore.

It was, “I work from home, b****es! DO YOU SEE ME? Do you see me IN MY PAJAMAS?!?! Take THAT, corporate!”

Is it just me, or is that really juvenile?

“Nobody takes my work seriously!”

At the same time as everyone was burning their ties and pantyhose, it was (and definitely still is) very normal to complain that nobody takes an ittybiz seriously.

The neighbors ask the Very Serious Business Owner to collect their FedEx packages while they’re out because it looks like they’re not doing anything.

The PTA asks the Very Serious Business Owner to man the cookie booth because it looks like they’re not doing anything.

The partner, the mother, or the sister asks the Very Serious Business Owner to drop off the dry cleaning because it looks like they’re not doing anything.

We like to sit around with our ittybiz friends and complain that nobody takes us seriously, but we’re not exactly wearing the badges of people who take themselves seriously.

I don’t know, but it seems to me that if a person were wearing what they would wear to IBM, far fewer people would be asking that person to hang around waiting for the courier to show up. It wouldn’t drop to zero, no. But it wasn’t zero when you were working outside the home. Plenty of people make plenty of inappropriate requests of non-ittybiz owners, too.

“But I don’t even see anybody!”

Comparably, this is probably true. You don’t see the receptionist, or your boss, or your boss’ boss. You don’t see the parking lot guy, or the client, or Linda from head office.

All of this is true.

But you do see the grocery store clerk and the coffee shop guy and, probably, the dry cleaner. You see the woman at those PTA things, and you see the mechanic, and you see the courier.

In my world, those people are not nobody. They’re potential clients and referrers. When you start looking at the world at large as a networking meeting rather than a forest full of nobodies, it’s amazing how dressing decently doesn’t seem like such a hardship anymore.

“But I’m so sick of wearing [suits / heels / bras / shirts]!”

Can I tell you something? Come real close so I can whisper.

Are you ready?

Sometimes I get sick of paying people.

It drives me nuts. I’ve been doing it for years, and honestly? Sometimes I get sick of it.

I get sick of washing dishes, I get sick of taking showers, and I get sick of vacuuming wood floors. (I got wood floors because I didn’t want to vacuum. Apparently, I have a tendency towards self-delusion.)

I get sick of flossing, and eating healthy food, and even unschooling. Sometimes I wish Jack would just go to school already.

There are lots of things we get sick of. That we are sick of them is not, in itself, is a good reason to stop doing them.

If we’re sick of something, the mature thing to do is analyze whether that something is providing value, whether the same value can be achieved another way, and whether the benefits outweigh the costs. “I hate it, therefore it has no value” is not a rational statement.

So where do we go from here?

At this point, some general advice would probably be in order.

1. Consider wearing something else.

You can wear whatever you like. You can wear whatever you like, you can wake up whenever you like, you can work wherever you like. Your choices are your own, and they always have been.

Even in corporate, you’re generally allowed tremendous freedom in what you wear. This isn’t IBM in the fifties. Nobody’s coming to your desk to measure your cuffs.

You’re allowed to do whatever you want. It just might be a worthwhile idea to actually think of what the best thing to do is, rather than doing whatever the hell you feel like and then expecting it to be okay.

2. “But people shouldn’t judge me for what I wear!”

If you don’t like it when your teenage son shows up in hair down to his nose and a faded black hoodie, you judge people on what they wear. If you don’t like it when his girlfriend shows up in a skirt with less cotton than an aspirin bottle, you judge people on what they wear. If you don’t like it when your husband wears socks with sandals, or tucks his shirt in, or doesn’t tuck his shirt in – congratulations! You judge people on what they wear.

You judge, they judge. It’s okay. We’re all friends here. But friends don’t let friends delude themselves. No, people shouldn’t judge you for not brushing your teeth for fourteen straight months, either – hey, it’s your mouth and you can do what you want with it – but they do judge, and they always will.

3. What rules do you expect other people to follow?

Unless you’re a celebrity under the watchful eyes of the paparazzi, no one is really giving a second thought to the particular clothes you are wearing. They’ll only notice if something is amiss. (Dave always says things like this are like plumbing – you only notice it when there’s a problem.)

Imagine you walked into a building where someone was professionally engaged in the same strata of pursuit as you. (In other words, if you’re a coach, compare yourself to a psychologist, not a sculptor.). What general standards would you expect that kind of professional to meet?

4. Would YOU take you seriously?

Now imagine that you’re in a lineup of 5 other people who do the same thing you do. Take how you’re dressed on your average Tuesday and imagine they are, as the saying goes “dressed for success”. Would you take yourself seriously as a contender? We’re not asking if you’d outshine them, we’re asking if you’d look like you’re phoning it in. To use the coaching example, do you look like a coach, or do you look like the coach’s cleaning lady?

5. Have you tried it another way?

“But I work fine in pajamas! I’m perfectly productive! That’s just the way I am!” is a common refrain, and it may have validity. But until you’ve tried it another way – and truly tried it – you don’t know if you’re most productive in pajamas. And doesn’t your ittybiz deserve you at your most productive?

It’s your business and you can run it any way you want to. If you’re experiencing all the success you ever dreamed of, and you get to do it looking like you just rolled out of bed ten minutes ago, then more power to you. But if you could use something to take things up a notch or two, dressing for work and seeing what it does for your ittybiz wouldn’t hurt.