How to Wear Dress Pants, If You’re a Guy: Don’t Wear Them With Sneakers and Avoid Khakis

Despite what you heard, don’t wear khakis.  Just because these men’s pants are classic, it doesn’t mean they’re timeless.  In fact, they’re starting to represent a dull and generic image for men’s attire.

Some articles of clothing go with anything, like Chuck Taylor’s.  Then there are specimens like Hawaiian shirts, that arguably go with anything simply because they clash with everything, technically meaning they go with everything.  And then there are khaki pants, which truly look good with anything they’re paired with, in theory.

But not for me.  I’m very particular when it comes to wearing khakis:

1)     They’re the same color as my legs, so I kinda feel like I’m not wearing pants at all.

2)     Because of their good reputation (“you can’t go wrong with khaki’s”) and popularity, they are a bit boring by now.  It’s assumed that a man automatically looks better because he’s wearing tan pants.  I say, not creative enough.  Deduct one point unless worn in moderation.

3)     Despite popular belief, they don’t truly look good with anything.

What has put these thoughts in my head?  Surely just random observances over the last twelve years:

1)     In high school, every Friday the football coach had all the football players wear khaki pants, a white dress shirt, and preferably a tie.  But  many of them wore running shoes.  It came across as predictable and forced to me (which it indeed was).  You want to look nice?  At least change the shoes.

2)     In the movie 40 Year-Old Virgin, Andy (the lead character played by Steve Carell) wears khaki pants in almost every seen.  His attire is most noticeably awful when he first goes to the night club wearing a yellow polo and khakis.  Nerdy, man.  Nerdy.  Same thing in Sideways with Miles (played by Paul Giamatti).

3)     In the past 15 years, khakis and polo shirts have become the official uniform for employees of places like Best Buy.  So now khakis are starting to represent a dull, generic work uniform.

Instead of khakis, try this. Note: Black shoes with black pants. Not brown shoes.

Khakis have become part of a stereotyped outfit of an outdated man from the year 2000: Khaki pants, faded polo shirt, cell phone holder on belt.

Noted, there is a difference between what a man wears to work and what he wears to every other public events.  I know for myself, I don’t care that much what my coworkers see my wearing as long as I don’t look like a slouch.  So yes, I do resort to polo shirts and once every week or two, I’ll wear khakis.

But for many, work isn’t as a professional environment as we often pretend for it to be.  I don’t take as good of care on the clothes I wear day in and day out to work.  Who cares if they’re faded or a little wrinkled?

Bottom line: For a man to truly dress nicely, and appear to be modern yet not trying too hard, he should simply try doing so sans khaki pants.

How?  Charcoal colored pants.  Dark brown pants.  Slate (very dark blue/gray) pants.  But not tan.  Heck, even dark jeans can look better than khakis when done right.

P.S.  If you must resort to wearing khaki pants in an attempt to look nice, do not be temped to wear a navy blazer or jacket with it.  That’s for CEO’s who are 61 years old and don’t realize that it’s no longer cool.  Wearing a navy jacket with khaki pants is for guys still wearing Levi’s jeans similar to Jerry Seinfeld in 1994.

And one more thing… Now that you’ve read my take on pants, why not read my perspective on being a dad?  That’s right- parenting from a dad’s point of view.  I have been documenting my thoughts as a dad since the week we found out my wife was pregnant.  I formally invite you now to read my “dad blog” by clicking on the link below:

dad from day one

I “Get” Conan O’Brien: Why So Many Americans Support Team Coco Over Jay Leno

In the Year 2010…  In the Year 2010…


I am one of those people who function best on 5 ½ to 6 hours of sleep a night.  Any more than that and I’ll wake up with a headache and the rest of the day will just drag by.  This is something I learned in high school (1995-1999).  And the way I found this out was by staying up every night to watch the then unfamiliar Conan O’Brien.

He acknowledged his audience: High school students, college students, and senior citizens.  Demographics showed those were the people who for some reason kept tuning in each night.  Those were the groups of people who “got” his kind of humor.  Such as:

A giant bear wearing a diaper who was put in a chamber with cash flying around who instead of grabbing for as much cash as he could during the 30 second time limit, he chose to grab… himself.

Staring contests between Conan and his sidekick Andy Richter with distractions on stage to make it for challenging for them both.  My favorite was when a robot came out on stage and sat down on a toilet.  The sound of bolts clanking into the bowl were heard.  Then the robot raised his arms in victory.

Andy Richter’s little sister.  She was in love with Conan and would sit in the audience in her pajamas and pigtails and rush up on the stage whenever she got a chance.  I remember having a crush on the 25 year-old actress who played her; it was her first role on TV.  Years later she ended up on SNL and eventually got her own show, Parks and Rec.  Amy Poehler.

Not Cool Zeus.  Conan would flip through his “special NBC satellite” channels to see what else was on while his show was on.  He watched a show called Not Cool Zeus where Zeus broke obvious social boundaries.  One time he drank milk right out of the container from the fridge, looked around to see if anyone was looking, then snuck it back in the fridge.  Another time he did a huge cannonball into a swimming pool right next to a group of people who were just chilling out.  Each time a red logo would be stamped onto the screen that read “NOT COOL ZEUS”.

Raymond, who gives away Preparation H to audience members and sings, “Raymond’s here, Raymond’s here”.

Triumph the Insult Comic dog: “For me to poop on!”

Secrets with Mr. T.

http://hornymanatee.com/

Twitter Tracker.

When it really comes down to it, Conan O’Brien is my favorite comedian on TV.  And he has been as long as I’ve been watching him.

I don’t “get” David Letterman’s style of humor.  I’ve tried.  I failed.  The dry, aimless, ad-libbing Midwesterner and his Jewish bandleader Paul Shaffer were never a team that pulled off keeping my attention.  I’ve never made it through a full episode of his, not even the ones where he heavily addressed his scandal.

But Conan’s randomness reminds me of the way my guy friends and I joke around.  It’s not vulgar.  It’s just weird and off the wall.

Conan O’Brien is much more scripted.  Almost too scripted.  And somehow that becomes an advantage instead of a downfall.  It’s part of the fun.  In a way it’s like he’s making fun of how organized the show is.  He has always mocked NBC and his writers.

Like a grown-up version of Pee Wee’s Playhouse where he is the only legitimate entertainer amongst a crew and network consisting of imbeciles.  And a creepy Jewish bandleader named Max Weinberg who just happens to also be Bruce Springsteen’s drummer.  That is solid.

And the fact that Conan refuses to change his Spandau Ballet hairstyle. And that he speaks in a 1940’s radio broadcast dialect.  And that he constantly makes fun of his pasty white skin and lanky 6’ 4” body.

Yet he comes across as the classiest late night host.  Conan is somehow timeless.

I remember a few years ago I remember thinking how weird it would be if any of the late night hosts themselves ended up in the headlines.  Because so much of their job is sarcastically commentating on what’s going on in the news.  Ironic.  Now with David Letterman’s sex scandal, Jay Leno’s failed new show, and Conan’s leaving The Tonight Show, all the bases are covered.

I will always be a Conan guy.  Whether he’s on NBC or not.