Q and Answer: Dressing for the IT Crowd
Jake’s sad story reads thusly:  I work in the IT department for a fairly large company.  Compared to  the amount of people working for the company the IT department is fairly  small.  This last year I’ve been trying to get promoted from system  administrator to senoir system administrator where I would actually be  managing people.  I’ve been told I have a good shot and that I’m the  most qualified to get moved into that position.  So, for the last year  I’ve been dressing the part of management. Everyday it’s nice dress  pants, a fitted button up shirt and a tie.  A few times when there are  meetings I wear a suit. I follow all the rules on your websites.  I even  brought all my pants to a tailor to have them adjusted because they  were too long. 
IT has always had a history of dressing… well a little  like IT:  Jeans, t-shirts, tennis shoes and polos are a very common  sight around the IT office.  I only wear jeans on casual friday and  never with a polo.  Here is my dilemma.  My attire has raised the  eyebrows of those who I hope to manage some day.  Suits and ties are  reserved for our salesmen and high up management (who all dress very  poorly.  So much pant leg pooling going on around here).  
How can I  dress up to be management material but still not lose my IT/geek  identity?  I don’t want to alienate those that I hope to lead some day,  and I definitely don’t want to be bunched in with the fist-bumping  salesmen of our company.  Is there a way to do this?
This is tough for me to read.  It amazes me that geeks - the very same people who got picked on for non-conformity in their school days - so often insist on conformity in the workplace.  To say nothing of the fact that the conformity they often demand is “we’re all equally slovenly.”  I don’t think that cursing your situation is the only answer, though, Jake.
The first step for you, I think, is recognizing the difference between dressing well and dressing up.
It sounds like you’re on that road already, but let’s go over it anyway.
Dressing well must always include situational awareness.  You dress to make an impression; to understand the impression you’re making, you have to put yourself in other people’s shoes.  Your choices have to be made with some understanding of what their effects will be, or you’re flailing blindly.  Other people’s opinions needn’t be the sole factor in deciding how you’ll present yourself, but they should be a factor.
In your situation, it sounds like you want to distinguish yourself from your peers without alienating them.  That’s a needle to thread, but it’s possible.  The key is to look like the sharpest, most serious IT guy, not like the most IT-guyish manager.  That might mean a blazer with jeans, or simply casual clothes that fit well and look good.  What it probably doesn’t mean is slacks, a dress shirt and a tie, which is pretty much the uniform of the bank teller (or sweaty widget salesman).
Unfortunately, we don’t get to pick how others see us.  We can, however, pick what we present to them.  And that choice can include anticipating their reactions.  It’s entirely possible to dress well without being a dick.

Q and Answer: Dressing for the IT Crowd

Jake’s sad story reads thusly: I work in the IT department for a fairly large company.  Compared to the amount of people working for the company the IT department is fairly small.  This last year I’ve been trying to get promoted from system administrator to senoir system administrator where I would actually be managing people.  I’ve been told I have a good shot and that I’m the most qualified to get moved into that position.  So, for the last year I’ve been dressing the part of management. Everyday it’s nice dress pants, a fitted button up shirt and a tie.  A few times when there are meetings I wear a suit. I follow all the rules on your websites.  I even brought all my pants to a tailor to have them adjusted because they were too long. 

IT has always had a history of dressing… well a little like IT:  Jeans, t-shirts, tennis shoes and polos are a very common sight around the IT office.  I only wear jeans on casual friday and never with a polo.  Here is my dilemma.  My attire has raised the eyebrows of those who I hope to manage some day.  Suits and ties are reserved for our salesmen and high up management (who all dress very poorly.  So much pant leg pooling going on around here). 

How can I dress up to be management material but still not lose my IT/geek identity?  I don’t want to alienate those that I hope to lead some day, and I definitely don’t want to be bunched in with the fist-bumping salesmen of our company.  Is there a way to do this?

This is tough for me to read.  It amazes me that geeks - the very same people who got picked on for non-conformity in their school days - so often insist on conformity in the workplace.  To say nothing of the fact that the conformity they often demand is “we’re all equally slovenly.”  I don’t think that cursing your situation is the only answer, though, Jake.

The first step for you, I think, is recognizing the difference between dressing well and dressing up.

It sounds like you’re on that road already, but let’s go over it anyway.

Dressing well must always include situational awareness.  You dress to make an impression; to understand the impression you’re making, you have to put yourself in other people’s shoes.  Your choices have to be made with some understanding of what their effects will be, or you’re flailing blindly.  Other people’s opinions needn’t be the sole factor in deciding how you’ll present yourself, but they should be a factor.

In your situation, it sounds like you want to distinguish yourself from your peers without alienating them.  That’s a needle to thread, but it’s possible.  The key is to look like the sharpest, most serious IT guy, not like the most IT-guyish manager.  That might mean a blazer with jeans, or simply casual clothes that fit well and look good.  What it probably doesn’t mean is slacks, a dress shirt and a tie, which is pretty much the uniform of the bank teller (or sweaty widget salesman).

Unfortunately, we don’t get to pick how others see us.  We can, however, pick what we present to them.  And that choice can include anticipating their reactions.  It’s entirely possible to dress well without being a dick.