Dear Son – Tip #4 – Wearing Hats

How the author/authors of this list go from pursuit of women, to sex, to hitting someone, to wearing hats is hard to follow.

This tip “Every hat should serve a purpose” is okay, not great.

Most hats are worn as a cover for delayed grooming. Bed head.

Still, hats are a part of most wardrobes. Since your wardrobe is that of a sports oriented young man, the hat you will wear most often is a baseball style cap.

They should be worn with the bill facing forward unless you are playing catcher. After a certain age, and you have passed that age, backwards facing hats do not compliment your wardrobe. Having played catcher for many years, the backward facing hat bill was normal.

Wearing a cap with the bill off to the side might be considered cool or fashionable, trust me – it’s not. It’s awful. You are worthy of looking intelligent. Bills to the side are not intelligent looking and are intended to look that way. If someone is intentionally trying to look dumb, let them. They probably are.

Most other hats serve you well in shading your eyes or head from the sun.

Other than that, hats serve little purpose other than complimenting a certain look and can be quite stylish.

The one that springs to mind in which young men incorrectly think a hat adds to the moment is the top hat worn for formal occasions and dances.

Nothing says moron faster than a young man at prom in a top hat.

Think “Dumb and Dumber”. The scene wear the two champions of stupidity wear top hats to a formal charitable event. They are mocked and ridiculed. Yes, it’s a funny scene; however, they are dumb and dumber.

If you ever run for office, never wear a hat unless you are at sporting event, in a sporting event, going out to get the paper in the morning, or are trying to avoid detection.

Think Mike Dukakis in 1988 running against George H.W. Bush. He wore a tank helmet in a tank in an effort to show that he was pro-military. He looked ridiculous and it might have cost him the election. It was that bad.

Generally speaking, hats are ok if they are worn for the setting in which you will find yourself.

Silly hats are for silly occasions. Avoid cameras in those situations.



Chris Saxman

About Chris Saxman

Father of four, small business leader, retired politician, and Executive Committee member and former Chairman of an international trade association, Chris Saxman delivers strategy and insight as a political coach and keynote speaker. Contact Chris.

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