When I’m not hosting my public radio show, The Sound of Young America, or my comedy show, Jordan, Jesse, Go!, my TV show, The Grid, or Put This On, I produce and serve as the bailiff on the Judge John Hodgman podcast. In the show, John (who you may know from the Daily Show or as the PC in the Mac/PC commercials) judges personal disputes, People’s Court-style. 

This week’s case was style related: a woman who was embarassed that her fiance went to work wearing torn jeans or cargo shorts and ratty t-shirts. His argument was that he was a programmer, and at least he wasn’t wearing a shirt with a unicorn on it. She countered that it was embarrassing to be seen with him.

You’ll have to listen to the show to find out what Judge Hodgman ruled. You can also download it for free in iTunes.

1. Get a soft-shouldered cotton sports jacket. I buy them whenever I see them. They’re pliable, comfy, and easy to pack. They do the job of a sweater but look dressier and have lots of pockets.

2. Cashmere sweaters, especially V-necks. Can’t have enough of those, whether they’re four figures from Hermÿs or two figures from Uniqlo. I actually once noticed a stylish Uniqlo salesman wearing two at the same time, in lime and in sea blue. A great look.

3. Good chinos or sporty flat-fronts are a must. Maybe my best casual pants are Helmut Lang from back when there was a Helmut Lang.

4. The button-down-collar oxford cloth shirt.

Glenn O’Brien on mastering business casual.
“It’s almost the end of the week, and there’s no better way to celebrate the weekend than to start early!!!! So please join the fun-makers and wear your Flip-Flops tomorrow, and EVERY Friday this summer.”

Actual quote from an actual work memo that an actual reader actually received.  I’m moving to Canada.

BREAKING NEWS: The actual reader informs me that HE LIVES IN CANADA!  THERE’S NOWHERE LEFT TO GO TO ESCAPE YOUR COLLEAGUES’ HAIRY TOES!

mrsartorial:

Jim Nelson, Editor-in-Chief of GQ out on the street and living the lifestyle. I’m definitely liking this tweed and solid gray tie combo; keeping it simple and classy.
prepidemic:

Nice and Casual


This is a wonderful example of a dressed-down suit.  This look would fly  in most business-casual contexts, with its relatively casual fabric and  simple styling.  It could also work in a more formal creative  professional’s wardrobe - say a designer or an ad executive.  Besides  all that, he looks great, right?

mrsartorial:

Jim Nelson, Editor-in-Chief of GQ out on the street and living the lifestyle. I’m definitely liking this tweed and solid gray tie combo; keeping it simple and classy.

prepidemic:

Nice and Casual

This is a wonderful example of a dressed-down suit.  This look would fly in most business-casual contexts, with its relatively casual fabric and simple styling.  It could also work in a more formal creative professional’s wardrobe - say a designer or an ad executive.  Besides all that, he looks great, right?

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?”

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.

“I love golf.” - This guy
Q and Answer
Tyson writes:
I try to present myself well at work.  I iron my shirts, shine my shoes, and try to match.  Some people may say, dress for the job you want.  What’s the PTO take?  I work in a khaki/polo/button down habitat.  A suit would be too much.  What are some nice styling’s that don’t scream look at my new suit, but still out-class Dockers and a semi-old Ralph Lauren polo.
Let’s start with the bad news: you can’t really wear a suit in a polos and Dockers business casual environment.  When you’re doing business, you always want to look as good as you can without seeming like a dick, and when everyone else is wearing polos, you’ll look like a dick in a suit (even with a tie).  Unless you’re meeting with clients that day, you’ll stick out like a sore thumb.
That doesn’t mean you have to dress like the guy pictured above, though, and it sounds like you’re well on your way to a better look.
No polos.  Don’t wear a polo shirt anywhere you wouldn’t wear shorts.  Playing tennis, weekend in the park, wear a polo, fine.  Having a meeting?  You can handle the five extra buttons and full sleeves on your shirt.  (No short-sleeved dress shirts, either, but that should go without saying.)
Don’t wear a tie without a jacket.  This is the fast route to looking like you work at Blockbuster or maybe, at best, are a teller at Wells Fargo.  Ties are meant to be worn with coats.
Watch your fit.  Most men wear casual pants like chinos way too long and way too baggy.  A trim, clean fit in your pants is key.  Buy them the right size and avoid pleats at all costs.  Similarly, your shirt shouldn’t pool out around your waist.  Buy a slim-fitting shirt, or take your shirt in to the tailor to get the waist taken in - it’ll cost $10 or $15 and make a huge difference.  A button-down collar is a nice way to keep your collar in check if you’re not wearing a jacket.
Wear good shoes.  A great pair of shoes will take you from boring to sharp.  No Kenneth Cole duckbilled b.s.  No corrected-grain leather with a plastic-y finish.  Rotate a couple pairs.  Wear a belt that matches.  No clunky rubber soles.  You work in an office, not on a marathon team.
Wear a sportcoat.  Even a quiet pocket square if your office won’t think you’re totally insane.  It shows that you care without showing anyone up, particularly since you won’t be wearing it around the office much anyway.  A nice cashmere sweater won’t hurt in the winter, either.
We’re essentially talking, here, about focusing on the fundamentals: wear quality clothes that fit.  Dress so that someone looking at you would think you’re someone who they’d trust to work with.

“I love golf.” - This guy

Q and Answer

Tyson writes:

I try to present myself well at work.  I iron my shirts, shine my shoes, and try to match.  Some people may say, dress for the job you want.  What’s the PTO take?  I work in a khaki/polo/button down habitat.  A suit would be too much.  What are some nice styling’s that don’t scream look at my new suit, but still out-class Dockers and a semi-old Ralph Lauren polo.

Let’s start with the bad news: you can’t really wear a suit in a polos and Dockers business casual environment.  When you’re doing business, you always want to look as good as you can without seeming like a dick, and when everyone else is wearing polos, you’ll look like a dick in a suit (even with a tie).  Unless you’re meeting with clients that day, you’ll stick out like a sore thumb.

That doesn’t mean you have to dress like the guy pictured above, though, and it sounds like you’re well on your way to a better look.

  1. No polos.  Don’t wear a polo shirt anywhere you wouldn’t wear shorts.  Playing tennis, weekend in the park, wear a polo, fine.  Having a meeting?  You can handle the five extra buttons and full sleeves on your shirt.  (No short-sleeved dress shirts, either, but that should go without saying.)
  2. Don’t wear a tie without a jacket.  This is the fast route to looking like you work at Blockbuster or maybe, at best, are a teller at Wells Fargo.  Ties are meant to be worn with coats.
  3. Watch your fit.  Most men wear casual pants like chinos way too long and way too baggy.  A trim, clean fit in your pants is key.  Buy them the right size and avoid pleats at all costs.  Similarly, your shirt shouldn’t pool out around your waist.  Buy a slim-fitting shirt, or take your shirt in to the tailor to get the waist taken in - it’ll cost $10 or $15 and make a huge difference.  A button-down collar is a nice way to keep your collar in check if you’re not wearing a jacket.
  4. Wear good shoes.  A great pair of shoes will take you from boring to sharp.  No Kenneth Cole duckbilled b.s.  No corrected-grain leather with a plastic-y finish.  Rotate a couple pairs.  Wear a belt that matches.  No clunky rubber soles.  You work in an office, not on a marathon team.
  5. Wear a sportcoat.  Even a quiet pocket square if your office won’t think you’re totally insane.  It shows that you care without showing anyone up, particularly since you won’t be wearing it around the office much anyway.  A nice cashmere sweater won’t hurt in the winter, either.

We’re essentially talking, here, about focusing on the fundamentals: wear quality clothes that fit.  Dress so that someone looking at you would think you’re someone who they’d trust to work with.