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“ARE YOU GOING FARMING?” Not a question you want to find yourself fielding at the water cooler, but when Glenn Yarris wore light-wash denim jeans and a thick belt to work, he received exactly this reaction—from his boss. Mr. Yarris, 32, had unwittingly strayed from the uniform of dark jeans and sport-coat to which the men at Humanscale, an ergonomic furniture company in Manhattan, hewed.

When the company shifted its dress code a couple of years ago from white-collar garb to business casual, the new rules left much open…