Over the Christmas holiday, Jordan and I had a bit of a discussion about our office’s dress code. I’d been fighting him for months, trying to get him to show up every day in a suit and tie.

Fat chance.

At my wit’s end, I decided that my New Year’s Resolution was to let this go, and we discussed a relaxation of the office dress code to “business casual.” Jordan gladly agreed,

Imagine my surprise when, on January 2, 2013, Jordan walks in wearing an untucked polo shirt, pleated khakis, and black sneakers.

“What the hell are you wearing?” I blurted.

“Dude, you said we were business casual! I’m biz cas!”

I shook my head. “I’ve made a huge mistake. Listen, Jordan, has anyone ever explained to you what ‘business casual’ means?”

The blank stare told me all I needed to know.

“Business casual.”

These two words strike fear into my heart, and make fools out of wise men.

I understand that there are some days that you just don’t feel like getting into the full suit rig for a day on the job. Hell, I was with you this week, and wore my L.L. Bean chamois flannel shirts to the office on the coldest of days this week.

Unfortunately, these days “business casual” has devolved into a nightmare — over-sized polo shirts with visible white t-shirts underneath. Poly/cotton blend pleated khakis. Backpacks. White athletic socks with black sneakers. It makes me shudder to think about it. Here’s a quick tip: there’s nothing “business” about sneakers.

You know, I can’t really blame men today for being clueless. In our increasingly casual American society — remember that we’re the country that invented Pajama Jeans — the line between casual and business wear has become too blurred, and there’s simply too little guidance for too many men today.

Today, I hope to be a beacon of guiding light.

What Does Business Casual Mean, Mister Fancypants?

To pass business casual muster, you should aim for “not quite a suit, but damn near close.” This is an outfit that will make you look sufficiently professional to impress a client who drops in for a surprise meeting, but not quite enough to appear in court.

I am going to bold this because it is important: business casual is not simply wearing a suit without a tie. That is called “wearing a suit without a tie.” Business casual is also not wearing a shirt, tie, and pants. You don’t look professional when you do this, you just look like Mr. Mackey, m’kay? Would you hire Mr. Mackey to be your lawyer?

No, true business casual is better than that. It’s more creative and lets you get some variation in your wardrobe.

There are several elements to the true business casual outfit:

  1. Blazer or sport jacket;
  2. Collared shirt;
  3. Wool trousers;
  4. Leather shoes;
  5. Tie (optional); and
  6. Pocket Square (optional).

Let’s run though these elements.

1) You should have odd jackets in your professional wardrobe

No, I don’t mean “strange” jacket. Rather, I mean a jacket that isn’t part of a suit. There are generally two categories of odd jackets, both of which are essential to your business casual wardrobe  — blazers and sports coats. You might not know that there’s a difference between the two.

Blazer

The term “blazer” originates with brightly colored English rowing club jackets. The original blazer was red. These days, you’re more likely to see them in navy, in either a worsted wool or a flannel. Most traditionally found with brass or silver-colored buttons, the navy blazer is classic “Ivy Style” wear.

You ought to own one, preferably in flannel. The great thing about a navy blazer? Even if you are dressed in a schlubby polo shirt, throw on a navy blazer and you’ll class yourself up by an order of magnitude. If you feel that the brass buttons make you look too much like an English schoolboy, try switching them out for horn.

Sport Coat

A sport coat, traditionally, was one worn during “sport” — like hunting — hence its name. These days, a sport coat generally refers to an odd coat that’s not made of a suiting material. You can usually get away with sport coats in slightly louder fabrics that might not be appropriate for a full suit.

Common materials for sport coats include tweeds, tan camel hair, birdseye/nailhead, and some more colorful plaids and checks.

Why have these?

Simple — they add diversity to your wardrobe and allow you to take the formality down a notch from the standard navy or charcoal suit. Or, in a pinch, you can throw on a jacket to spruce up an outfit that’s a bit less formal.

Moreover, there are literally thousands of different materials you can use to make a sport coat. Take a look around and find a fun pattern to wear every once in a while. You think it sounds boring? — take look at a local attorney pal of mine who looks better in business casual than most people look in a tuxedo.

That’s business casual done right.

2) Collared Shirt

I’ve written many, many words about shirts before , so I will keep this to a minimum. Your business casual shirt should follow four rules:

  1. It should be blue, or white, or both (stripes and checks are ok);
  2. It should be ironed;
  3. It should have button cuffs; and
  4. Polo shirts don’t count.

Seriously guys, polo shirts aren’t formal clothing, they’re glorified t-shirts meant for playing golf or tennis. Stop wearing them in professional settings.

3) Wool Trousers

Just as you should own several odd jackets, you should own several pair of trousers that aren’t part of a suit. Why? Versatility, and appropriate business casual wear.

First, let’s get something straight — khakis are NOT business casual. I don’t care what your favorite style columnist says, or what the salesperson at the local Menz Discount Suit Deal$ store tells you. Khakis are essentially jeans that are tan instead of blue. Stop wearing them in a professional setting. You look stupid, juvenile, or both.

Instead, you should have is at least three pair of gray wool trousers: light gray, mid gray, and dark gray. Don’t believe me? Listen to this guy who has worked at J. Press probably for longer than you’ve been alive. I prefer flannel trousers — they have a better texture and are less likely to be mistaken for mis-matched suit pants. Plain wool trousers in light, mid, and dark gray are versatile enough to go with virtually any shirt, jacket, and tie combination, and will spruce up your look from khakis. Whether you get flat front or pleated is up to you — I own both.

Make sure that you get them altered properly (both in waist and leg length) and get them cuffed. Anyone who tells you that cuffs are for old men is stupid and wrong.

4) Shoes

We’ve already been over this before. The nice part of a business casual outfit is you’re afforded an extra bit of leeway with shoes — you don’t have to stick with just a black or brown cap-toe. Try a burgundy loafer,  a shell cordovan plain-toe blucher, or a tan semi-brogue.

Sneakers are always unacceptable. Vibram Five-fingers should be grounds for disbarment.

5) Tie

Chose your own adventure:

5a) I hate wearing ties!

Good news! You don’t have to wear one if you’re in a business casual outfit. Consider a pocket square, though, to spruce up your appearance. Make sure that if you’re not wearing a tie, and are instead wearing your collar unbuttoned, that you have a v-neck undershirt on so it doesn’t show. Undergarments should not be seen.

5b) I love wearing ties!

Good news! The business casual environment gives you a bit of extra leeway with experimentation. Bring out those ties that might be less appropriate with a full suit — like knit, wool, or bow ties. Your imagination’s the limit.

6) Pocket Square

If you’re not wearing a tie, you should have a pocket square. If you don’t own any, buy some. Start with white linen.If you are wearing a tie, tread lightly. Don’t get too matchy-matchy with your tie. Burn any matching tie and pocket-square sets you own.

In either case, stick with plain white linen if you’re an amateur. Cream silk is a good second choice. If you’re feeling more adventurous, follow this sage advice.

There’s your primer on real business casual dress. Feel free to ask additional questions or berate me in the comments below. Happy New Year, and until next time.

(image: young casual man going thumb down from Shutterstock)