How to Wear All Black, If You’re a Guy

Now that you’ve mastered How to Wear Pink, If You’re a Guy, try something even more difficult: black.

Gone are the days of the 1950’s beat generation or the grunge scene of the ‘90’s where dressing in all black meant you were a cool in a mysterious and artistic way. Today if a guy dresses in all black it sends one of the following wrong messages to the world:

1)     “I have recorded my own album called ‘Rock Tyme Central’, featuring me on electric guitar, keyboards, vocals, and back up vocals.”

2)      “Every once in a while, I put my tongue ring back in just to keep the hole from closing up.”

3)     “I worship Satan.”

When choosing to wear a black collared shirt, whether it’s a polo or long sleeved button down, unless you’re wearing with it dark jeans, you’re making a risky move, because you must carefully plan everything else you wear with it.

And since black shirts don’t usually work well with khaki pants (just like you can’t wear brown shoes with black pants), you will ultimately end up wearing some form of black pants: dark gray, charcoal, or faded black.  So technically, that means you’re wearing all black.

But these days, the only way to wear all black if you’re a guy is to not literally wear all black, but instead, pay tribute to the idea.  To pull this off, you must incorporate a color accent, or distraction, against the uniform consistency of your “all black” attire.  Like a blue t-shirt underneath your black shirt that barely shows through.  Or a white belt.  Or really nice Diesel style shoes with color in them- but not regular sneakers.

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