Sport Shirts: Beware

Dapper District has been sought by a friend to perform a consultation on this brown sport shirt.  What can be done with it? he asks.

Dark khaki and brown can be difficult to work with.  They keep you from wearing black shoes, but wearing brown shoes with a brown shirt tends to look kind of...brown.  You could try wearing sneakers, but sneakers will look dissonantly casual against a sport shirt.

But fear not!  There is a solution: my favorite color for pants, stone.  Stone is that kind of off-white-but-not-tan color of gray/brown you can get with ease at the Gap or J. Crew.  Not as limiting as the brown/denim combination.  Roll the sleeves up.  Now, you are definitely earthtoned but not in a really dark and dreary way.

You'll have to break out of the ordinary with your footwear.  Now would be the perfect time to experiment with some Soludos. 

Wear it with an unstructured odd jacket.  (You have a well-tailored white linen jacket, don't you?)  Excessively loud pocket square.  No neckties.  Consider leaving the shirt's top two buttons open, but not if you're wearing a round-neck undershirt.

Basically, you have to dress the outfit down somehow.  Successfully dressing up a brown sport shirt up is nearly impossible. 

And whatever you do, tuck it in.