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But these days, he’s gunning for supreme comfort, no matter how that looks.

Parra-Orlandoni, the head of product at a Manhattan marketing firm, had long favored jeans and button-downs for the office. “Are you really wearing that to work?” asked Ivan Parra-Orlandoni’s wife one morning last month as he headed out the door-the third time that week she’d posed the question. Ivan Parra-Orlandoni, a product manager at a Manhattan marketing firm, in his breeziest office attire. “You can wear a T-shirt and jeans and look put-together, but if it’s too baggy, you look like you rolled out of bed.” To do this, go at least “slightly dressier than working from home,” advised Peter Nguyen, a New York personal stylist to men in tech and finance. More ambitious types, he said, “would not wear cargo shorts.”Įven so, it is possible to dress breezily and “project an image of capability,” said Mr. Peter suggested that employees who dress down to the extreme are telegraphing an “I don’t care anymore” attitude. Maskin, who’s not above sporting Birkenstocks at his desk. “People are encouraged to wear shorts, sandals-anything that will make them comfortable, because we want them to do outstanding work,” said Mr. In this workplace Wild West, is there anything that can’t pass as “work appropriate”? Barely, said Alan Maskin, 68, a partner at Olson Kundig architecture firm in Seattle. PRESENTATION IS EVERYTHING Though cheerful, cabana suits are too casual for the conference room.