We’ve gotten some lovely responses to our post about an IT guy who wants to dress better.
Elly appreciated the distinction between dressing up and dressing well.
I have a lot of male friends who sometimes seem to not care about their  appearance, and then when they do get ‘tarted up’ for a night out, look  (a little) like a kid in their dad’s wardrobe. It’s good advice to know  about appropriate (as in, for the situation, rather than, say, adhering  to boring conventions) and stylish dressing and how it doesn’t have to  mean suit + tie = yawn.
Brett has been carefully treading the middle road.
I  have been dealing with a situation very similar to Jake’s.  I’m in  IT and see the same things. But I have done exactly what you offered to  him and it has been successful. Typically, I wear a good dress shoe, a  pair of dark wash Levi 514s, a fitted dress shirt, and a nice blazer.  When running around outside, I throw on my aviator-style sunglasses  for eye wear snaziness. It looks sharp but not precocious; noticeable by  management, but not over-done. And the wife takes extra notice of my  sharpness, which is really the only reason a guy needs for dressing  nice! 

I started trying  to take it to the next level with a  tie every once in a while but management always stared at me and asked  if I had a job interview (yes…in my jeans…). They’ve gotten used to  the tie not being an interview indicator, but i think I might stop for  summer because it does look pretentious around here. I can still pull  the tie off with a nice cardigan or v-neck sweater in the fall/winter as  it doesn’t look as formal as a coat and tie. Pocket squares are (sadly)  out-of-bounds for sure. 
Anyways, tell Jake to keep with it. You can still be  in IT and look sharp without losing the geek cred.
One anonymous writer tells us that he’s found the benefits outweigh the costs:
I recently have been working with that exact problem. My IT firm is  smallish and I started to dress well in a bid for management. At first,  my fellow IT folk balked at the change (and to this day comment  regularly). Soon however, they stopped. It wasn’t because I was geek  chic or whatever else you would want to label it, it’s because I was so  good at the job it didn’t matter what I dressed like. It’s well known I  am the most ambitious person in the dept and I have the skills to back  it up.Looking good is important. People listen to the best dressed guy in  the room. They will listen a second time if you are useful when you  talk.
If you have thoughts, share them with us.  Our email is contact@putthison.com.  And if you ever feel boxed in, just ask yourself: “What would Cary Grant wear?”

We’ve gotten some lovely responses to our post about an IT guy who wants to dress better.

Elly appreciated the distinction between dressing up and dressing well.

I have a lot of male friends who sometimes seem to not care about their appearance, and then when they do get ‘tarted up’ for a night out, look (a little) like a kid in their dad’s wardrobe. It’s good advice to know about appropriate (as in, for the situation, rather than, say, adhering to boring conventions) and stylish dressing and how it doesn’t have to mean suit + tie = yawn.

Brett has been carefully treading the middle road.

I have been dealing with a situation very similar to Jake’s.  I’m in IT and see the same things. But I have done exactly what you offered to him and it has been successful. Typically, I wear a good dress shoe, a pair of dark wash Levi 514s, a fitted dress shirt, and a nice blazer. When running around outside, I throw on my aviator-style sunglasses for eye wear snaziness. It looks sharp but not precocious; noticeable by management, but not over-done. And the wife takes extra notice of my sharpness, which is really the only reason a guy needs for dressing nice! 

I started trying to take it to the next level with a tie every once in a while but management always stared at me and asked if I had a job interview (yes…in my jeans…). They’ve gotten used to the tie not being an interview indicator, but i think I might stop for summer because it does look pretentious around here. I can still pull the tie off with a nice cardigan or v-neck sweater in the fall/winter as it doesn’t look as formal as a coat and tie. Pocket squares are (sadly) out-of-bounds for sure. 
Anyways, tell Jake to keep with it. You can still be in IT and look sharp without losing the geek cred.

One anonymous writer tells us that he’s found the benefits outweigh the costs:

I recently have been working with that exact problem. My IT firm is smallish and I started to dress well in a bid for management. At first, my fellow IT folk balked at the change (and to this day comment regularly). Soon however, they stopped. It wasn’t because I was geek chic or whatever else you would want to label it, it’s because I was so good at the job it didn’t matter what I dressed like. It’s well known I am the most ambitious person in the dept and I have the skills to back it up.

Looking good is important. People listen to the best dressed guy in the room. They will listen a second time if you are useful when you talk.

If you have thoughts, share them with us.  Our email is contact@putthison.com.  And if you ever feel boxed in, just ask yourself: “What would Cary Grant wear?”