7 Retirement Shirts I Won’t Be Wearing

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7 Retirement Shirts I Won’t Be Wearing


5 Ways You Are Wasting Money Without Even Realizing It

July 16, 2017

When it comes to retirement, many people talk about how much of a lump sum they will need to make work optional. They discuss their future plans full of travel, golf, grandchildren, and giving back to charity. We often hear of the dreams of starting the business they always wanted to run and starting the volunteer work they never had the time for when they were working full time.  Over the past twenty-six years, I’ve seen many people retire and helped many retire successfully.

At the risk of offending someone out there (because I am sure I will) I spent a few days up in New Jersey over the Fourth Of July and I saw a lot of bad shirts.  I mean really bad shirts.  Don’t know why it got me to this off the beaten path retirement topic, but I thought I would share my list of seven shirts you’ll never see me wearing during retirement.  Remember, if you do end up at Leisure Village, their motto is “It’s the time of your life to have the time of your life!”  Unless of course you are wearing a really bad shirt.

  • Tabasco Button Down Shirt – Don’t get me wrong, I love Tabasco sauce (especially the Pepper blend) but I wouldn’t wear a McIlhenny & Co. printed shirt with shrimp even if I was walking on Bourbon Street. I forbid this one in retirement.
  • Golf shirts with pictures of golf stuff on it – If you want to play golf in retirement, then I recommend you get as much of it as you can. However, having your attire loaded up with pullover shirts full of antique golf clubs and balls is a no no in retirement.
  • 80’s Cosby Sweaters – This isn’t just because of the whole recent Cosby situation, but these sweaters were god awful in the 80’s and one of those things sure not to make a fashion comeback.  If you are wearing one of these in the winter, then you better be sure it is for a retro 80’s party and that’s it.
  • Tommy Bahama – I know someone reading this really loves Tommy Bahama and I don’t begrudge you for that, but if you live In Hawaii (and Hawaii only) these make more sense to me. The rest of you…not something for retirement and not something I would be wearing in retirement.  I don’t get the whole palm tree on every single shirt look.
  • Tank Tops – Unless you are ready for a game of 3 on 3 basketball and have made the senior circuit of Ice Cube’s new league, the white tank top is a go (even if you do live on the Jersey Shore).  The tattoos won’t look quite as cool at the age of 70 as they did when you were thirty.
  • Abstracts – Triangles, circles, squares, you name it.  The bottom line is that all abstract t-shirts, button downs, jackets, etc. are all out of the question.  You don’t want to have the final phase of your life represent the beginning part of your life.  Look back at some of your old art you did as a kid.  It wasn’t good.
  • Shirtless – For 99% of us, all of the CrossFit, yoga, running, and weightlifting won’t help us defy gravity.  No problem at all with those retirees that love to garden, but nothing worse than seeing a 77 year old man doing their yard care shirtless.  You have to know when to call it quits. And I will make sure to stock up on cotton t shirts in retirement and never go for this look.


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