Going Sockless
Commando Ankles.
If you wear bespoke shoes, you can do whatever you want. You’ve paid your dues, and won’t look like you crashed on a friend’s couch and forgot to throw on socks. Basically, at some point you have to put in a little effort to successfully pull off the effortless look.

Socksless: Consider it a faux-pas and resort to a proper ankle sock in a fine gage mercerized cotton.
Things to Consider
You might look comfortable, but are you actually?
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The use of band-aids and foot powder are usually a sign that you are not comfortable.
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If you sweat, wear socks. Most people sweat.
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Sockless is not a good business look. It’s actually not a look at all.
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Dress shoes and no shows just don’t go together.
An Achievable Look If
You are of Mediterranean descent.
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You are an editor at a second rated
men’s fashion magazine.
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You can pull off a silk neck scarf.
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You have a permanent tan and
you are related to George Hamilton
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You belong to a country club of like-minded,
plaid-blazer and-penny-loafer-wearing individuals.
