ASK STONE - Should Men Wear Dress Socks All The Time?

Posted on April 11, 2014 by Roger Stone

Should men wear dress socks all the time? Is it ever appropriate not to?     - C.S Boca Raton, Florida

Fine socks should be worn for all business or formal occasions. Going sock-less, say with a pair of vintage gucci loafers is a preppy look picked up by Italians, a great look for casual occasions with khakis, Nantucket red trousers or jeans.

Bare ankles  go only with slip on shoes. Any shoe that laces or buckles needs a sock. Thomas Browne is wrong about this. A suit demands a sock. Socks must be calf length. Nothing ruins a ‘look” while seated than big old white hairy calves showing.

An example of the appropriate time to NOT be wearing socks with dress shoes.





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