You’ll Never Be This Cool

Kris Kristofferson.  One of the best song writers of all time.  If you’ve never heard Sunday Morning Coming Down by him, kick yourself.  Then listen to it.


If you don’t know that this is Willie Nelson kick yourself again.  His voice is my favorite on earth.  Listen to You Were Always on my Mind.  You’re going to have a sad day if you keep taking these suggestions just so you know.  Chances are it’s either raining or snowing where you are so I say go for it.  You should think about wearing outfit shown below for New Year’s Eve.

Johnny Cash at Folsom Prison in 1968.  The man in black wears a blue turtleneck/mock neck?, eh.

And down on his luck below in 1965.

I know you already know you’ll never be as cool as Bob Dylan.  If you don’t you are delusional and should immediately 51/50 yourself.  When having trouble deciding what to wear a good question to ask yourself is, ‘what would Bobby D do?’.


Merle Haggard’s music is really the coolest thing about him.  But this outfit is cool, especially that hat.  If you know where I can find one please tell me.

Robert Plant.  The guy performed in a kimono and still looked cool for christ’s sake.


It’s humbling to remember, it’s all been done before.  Just wear it well my friends.



About Leo Plass

Casual Elegance. I'd be happy to answer any style quandaries. Send them my way to if you dare.


  1. michaelvonbraithwaite

    Oh! I’m totally going to do a female version of this on Monday. Blogmate call and response!

  2. Pingback: You’ll Never Be This Cool: Space Between Edition « Ironing Board Collective

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  4. Pingback: You’ll Never Be This Cool: PRINCE Edition « Ironing Board Collective

  5. Pingback: Robert Plant | Trends Pics

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