Is it okay to wear a Sportcoat with Shorts?

From the Mailbag:  Thoughts on pairing a sportcoat/blazer with shorts

Originally Published 6/14/12.  Unstructured blazer, oxford shirt, & shorts all by GAP. Loafers by Sebago. Sunglasses by Ray-Ban. Beer by Pabst.

Hi Joe,

Sportcoat and shorts.  Thoughts, oh yoda of menswear?

– Shawn
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Yoda?  Nice.  I’ll take that title.  Let me attempt to channel the green one:
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All but impossible, wearing a blazer with shorts is.
This Venn diagram, of times when they look good together you see?
Cross their paths not.

But look great with a blazer, a kilt will.  Herh herh herh.
If with a blazer a kilt looks better?  Tell you something about shorts, that should.

Extremely rare times there are… when work, shorts and a blazer can.
Already be wearing shorts, you must.  Outdoors must you be.  Go down, the sun must.
Cold very quickly it gets?  And nearby, your completely unstructured cotton sportcoat is…

To hell with it then.  Cross this stylistic Bering Strait you should, open another beer you shall…
And with confidence wear.