Dear Crabby, What Was Your Worst Wardrobe Mistake?

Dear Crabby, What Was Your Worst Wardrobe Mistake?

Sincerely, Happy Colors

Dear Happy,

If there was a wardrobe mistake to make, I’ve made it. From flip-flops to Chelsea boots and from two-toned Oxfords shoes to boat shoes, I’ve tried it all. But my mistakes weren’t just in foot wear. I’ve had Zoot suits, leisure suits, and double-breasted suits, as well as, high-waisted trousers and low-waisted pants. I’ve wore floral print shirts and flannel shirts (still do actually). I’ve had skinny ties and wide ties. And I had the dreaded bell bottoms.

My father used to tell me to save all my ties, because they come in and out of style. That’s good advice, however, at this point in my life I really don’t wear ties, except to weddings and funerals. I find that a medium-wide tie works well all the time no matter what the current fashion trend is. The rules keep changing, but there are some you can rely on.

Here are some standard rules:

Dear Crabby sits infront of his laptop
  • Don’t mix patterns
  • Don’t wear shorts with a blazer or jacket
  • Dress to the specifications required
  • Don’t wear white between Labor Day and Memorial Day
  • Don’t wear suspenders and a belt at the same time
  • Match your color palette to the season
  • Never wear sneakers with suits
  • Don’t mix black and brown or black and navy
  • Don’t wear a vest on its own
  • Don’t button the last button on a jacket or sweater

My worst wardrobe mistake is really following whatever the current trend is, the best rule is keep it simple and traditional, at least for us men. Oh, and never, ever wear bell bottoms, that trend was pretty bad.

Hope that helps,

Dear Crabby.

About Dear Crabby

Stuck in a rut? Need some biased advice from a crabby old baby-boomer? Read regularly by thousands and loved by some, Dear Crabby answers questions weekly to life's challenges. Send him a note at

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