Biz Features

Dressing for Success =/= Dressing Up, or How To Read a Business Tip Article

by . December 16th, 2014

A few of our recent posts have been general men’s style guides, and as we and many commenters pointed out, these style guides don’t work in a lot of contexts.


Of course they won’t. We all live in different markets. What works for San Francisco won’t necessarily work in New York. Hell, what works in Queens might not even make sense in Manhattan.

A huge problem with any style guide – indeed any guide – is while readers often sort of understand the points any halfway decent author tries to make, not everyone has the sense to understand how to apply what they learned in their own contexts.

So, no you don’t have to be rail thin and 30 to pull off a current look, and yes it would be weird to wear a wool suit in a tropical country.

But several points remain :

  • If you dress poorly relative to what your market expects, you might lose potential clients or customers before they even get a chance to know you better.
  • If you look like a slob, it will be harder to gain respect from employees.
  • Blue collar workers have a different general culture from white collar workers.
  • Dress too differently from people around you and people will think you’re pretentious.
  • If you are in a creative field, a poor sense of style can reflect poorly on your attention to detail.
  • If you are in management, it can reflect a failure to understand social norms.
  • If you’re too avante-garde, you can look like a major a-hole to other people.

These are not meant to be right. They are meant to be true.


People can be –and are – terrible to each other.

Should we be free to dress however we like? I sometimes don’t even know any more.

Whether we like it or not,  we are constantly being judged by others – both consciously and unconsciously. And if you say you don’t do that to other people, you are at the very least lying to yourself.

We shouldn’t judge people based on appearances. But we do it anyway. We don’t feel comfortable leaving our wallets out in public solely on the shared notion that it’s wrong to steal either.

Which brings us to our next point:

 Context matters. Always.

Whether it’s deciding how best to dress for the occasion or how best to understand something, knowing context should be an overriding principle of yours – especially if you run a business.

If you don’t understand how or why other people would react to the things you do, you probably should reevaluate if you actually want to run an enterprise.

Yes, in principle however you dress should not matter, unless there are practical concerns, such as safety or comfort for instance. But in the real world, it absolutely does make a difference if you want to take your business as far as it can go.

By the same token, just following whatever some writer on the internet says about how you should dress, or hold your Christmas parties, or do your taxes without taking personal context into consideration is just all kinds of silly.

 You are responsible for how others see you.

On the other hand, the responsibility of the audience to understand context doesn’t give anyone license to be awful communicators. If anything, communicators should be as unambiguous as possible.

And we can only do that by understanding the kinds of people we each, and how we appear to them.

And yes – clothes do make a difference.

What will you wear tomorrow?

Photo credit: Sonia Belviso via photopin cc

Posts you might be interested in:

How do you keep fit? Comment below!


Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.