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Khakis have become part of a stereotyped outfit of an outdated man from the year 2000: Khaki pants, faded polo shirt, cell phone holder on belt.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

Comfortable Friday


 

Of all people, I should appreciate the quirky American tradition so many offices participate in once a week called Casual Friday.  After four hard days of working while dressed in a restricting long sleeve shirt, tie, and pants (or at least a polo shirt and khakis), the dress code nearly disappears on the 5th day.  Jeans, t-shirt, and flip flops are completely acceptable.  Goofy.  Just plain goofy.


 

The whole idea behind dressing professionally for work is to establish a mentality for the workers to act the way they dress. It also helps draw lines between superiors and those who answer to them, as managers and bosses tend to dress a little nicer, accordingly. But then that all goes away on Friday.  The playing field is leveled out, according to appearance.


 

If the way a person dresses does indeed reflect their initiative and performance at work, why play around with that once a week?  The answer:  It must not really make a difference.  Often, Friday is my most productive day of the week.  And I’m dressed like it’s Saturday morning.


 

Last week’s rerun of The Office addressed some of the tackiness that often accompanies Casual Friday.  Meredith’s lack of clothes, Oscar’s nasty feet, and Toby’s clashing colors.  It just makes me laugh: the double standard of dressing professionally for 80% of the work week and dressing like a slouch for the other 20% of it.


 

Typically on Fridays I wear my comfortable, worn-in/worn-out jeans (circa 2002 so they’re that light shade of blue that used to be the standard), along with a comfortable t-shirt (usually something I got for free from an event I participated in during 2002 and should now only be wearing to wash a car or do yard work in) and my 2002 Etnie skate shoes I wear not because I skate, but because they’re so comfortable- I refer to them as my Marshmallow Shoes because they’re so soft and cushioned.  The obvious recurring theme: clothing from the year 2002.  The other obvious recurring theme: comfortable.


 

Casual Friday is really Comfortable Friday.  If I dressed casually on Fridays, I would wear slimmer fitting darker jeans, an untucked collared shirt, and sneakers.  But I don’t.  And while I call it Comfortable Friday, “comfortable” can easily become a synonym for “sloppy”.  Sloppy is in the same word family as “slob”.  Slob Friday.  But I’m not complaining.  Some people like to play dress up to look and feel important at work.  For the rest of us, there’s Friday.


casual Friday