Working Business Casual into the 50-Year-Old Dress Code

by Rachel Yeomans | October 12th, 2009   

I came across this column on, and found it very insightful and appropriate in regards to casual attire and working with this attire from an older age group. Read on to see what contributing writer Terry Mackin has to say on dressing the 50-year-old casual businessman. I happen to disagree with a few points for workwear, as in the large sweatshirt and velcro for sneakers, but the humor is well-founded and the bottom line of being appropriate rings true. Click HERE for original article.

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A few years ago, local public schools were mandating dress uniforms and there was some grumbling.

“Wait a few years,” I wrote at the time. “Trust me. You’ll learn to love school uniforms.”

As a Catholic school kid who grew up to become a Catholic school parent, I knew that school uniforms simplified shopping and eliminated choice.

Growing up, the Sears catalog was our mall. At an early age, I learned to appreciate painless shopping for school clothes that were plain, predictable and within code.

I like school uniform dress codes so much that I wish we had them for adults in everyday life.

I have yet to determine the true meaning of “business casual.”

Should I wear a suit, tie or neither?

Jeans or Dockers today?

At age 50, I buy basically the same clothes, same brands, in the same colors anyway, although my sizes can vary, depending on the season.

Here’s my first shot at a uniform dress code policy for all average guys age 50-plus:


* Only khaki pants and khaki shorts are allowed. Recommend slacks have that magic piece of elastic on the sides of the waist, especially for holiday flexibility.

* No cargoes allowed. More pockets means more space to store useless, unhealthy stuff that will go through the washing machine.

* The length of your long pants should be to the tip of your shoe. Old guys in capris look silly.

* The length of your shorts should be at the knee, minimum. It may have worked for Larry Bird and Magic Johnson in the 1980s. But you look creepy in short shorts.

* A belt is required. Have a trusted family member or friend take an oath to tell you when you reach that milestone when you are inclined to wear your pants so high that that you don’t really need to wear a belt — or shirt.

Picture125 Working Business Casual into the 50 Year Old Dress Code Picture126 Working Business Casual into the 50 Year Old Dress Code


* Wear only dark, solid shirts. Keep the stripes or plaids for holidays. Shirts must cover all of your stomach.

* Sleeveless shirts are OK. But please do not use a white solid-stick deodorant.

* Novelty T-shirts are OK. But be tasteful. Two rules: 1. If you wouldn’t say it to your daughter and her friends, then don’t allow them to read it. 2. If it rhymes, reconsider.

* Encourage that your name be embroidered or screen printed on the front lapel of all shirts. First and last names. Your high school and graduation year are optional. Life Name Tags. Just think how many awkward conversations you could avoid.


* Tennis shoes are fine. But they must be tied at all times. If you can’t tie them, go Velcro if you don’t mind dressing like a kindergartner.

* Sandals work for some guys. But if you feel a little silly wearing them, you probably look a little silly so go back to sneakers. Sandals and socks are cool. You’re 50, remember?

* You don’t have to wear socks unless you are going bowling or shoe shopping. Any color of socks is fine. You’re 50. Nobody is looking at your socks.

boatshoes Working Business Casual into the 50 Year Old Dress Code


* Big, baggy sweatshirts and sweaters can be worn at any time. Hold it up. If it looks big enough to cover the dining room table, it’s probably just right.

* Sweaters must be worn and not tied around your waist or shoulders unless you own a major league sports team or have a hole in the seat of your pants.

sweater Working Business Casual into the 50 Year Old Dress Code

Hats, hair, accessories

* Wear your hair anyway you want. Just be glad you have hair.

* Ditto for facial hair. If it works for you and your special one, it works for us, big guy.

* You can wear any style of hat you want. It must always be taken off during meals, church and the national anthem — or we can take it off of you and stomp on it.

The Secret Weapon

* Every guy age 50 and more needs a navy blue blazer in his closet. Navy blue blazers are business, casual and/or business casual. It’s cool with blue jeans, dress slacks or Bermuda shorts. You can wear it to church or ballgames. You can wear it with a tie or a T-shirt. When in doubt, go with the traditional, reliable navy blue blazer, and you’re forever cool and within life’s dress code.