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Should all middle-aged executives adopt the Steve Jobs look?

In this Jan. 15, 2008, file photo, Apple CEO Steve Jobs holds up the new MacBook Air after giving the keynote address at the Apple MacWorld Conference in San Francisco. Apple on Wednesday, Oct. 5, 2011 said Jobs has died. He was 56.

File photo | AP Photo | Jeff Chiu/File photo | AP Photo | Jeff Chiu

The question

What do you think of a black cotton turtleneck, loose jeans and running shoes as a work uniform for a middle-aged executive, à la the late Steve Jobs?

The answer

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The story, according to Jobs's biographer, is that the recently deceased CEO was interested in giving his employees comfortable work uniforms like those he had seen at a Sony plant in Japan – Issey Miyake designed nylon jackets with detachable sleeves. For Apple workers, a black vest was envisioned, but it didn't fly in individualist America. Jobs, though, decided that he liked the idea of a uniform for himself and so bought hundreds of identical plain black Miyake mock turtlenecks. I can see why his employees rebelled against having to dress like a craft-fair organizer or reiki practitioner.

A loose, long-sleeved T-shirt (which is basically what a turtleneck is) is a shapeless garment that accentuates less-than-developed arms and shoulders. Yet in the weeks following Jobs's death, sales of posture-revealing, saggy black turtlenecks soared (although possibly only in preparation for Halloween costumes). Of all the brilliant trends Jobs sparked – many of them, paradoxically, design trends – the sartorial one was not his best contribution to humanity. Note to middle-aged executives: Extremely plain functional clothing does not, paradoxically, make you look unconventional; it makes you look square and old.

Russell Smith's latest novel is Girl Crazy . Have a fashion question? E-mail style@globeandmail.com.

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