PARKAS HAVE a certain burly charm. But with spring inching closer, who could blame a style-minded man for thinking about dressing a little lighter, looser and—dare we say?—more daringly. Dispensing with socks. Indulging in some Bradley Cooper-esque stubble. Wearing a color that doesn’t naturally occur in the fur of a rat.

Anytime you venture into trendier territory, however, you face new dilemmas. Not all trends are created equal, after all. Some provide a welcome change; others have outlived their moment; still others should never have had that moment in the first place. It’s all a matter for healthy debate, especially when it comes to looks that might be appropriate at the beach or a country club but won’t pass muster at any workplace that isn’t an art gallery/advertising agency/strip joint. “I think spring is a little more treacherous” than fall in terms of taking trends to work, said Kevin McLaughlin, co-founder and creative director of the Brooklyn-based clothing line J.McLaughlin.

Still, even if you’re only loosening up your look during off-hours, surely one or two of the following of-the-moment expressions are worth attempting. How to do it? “If you want to try a trend, pick one, not four. That’s always been my rule,” counseled New York-based menswear designer Todd Snyder. Let the debate begin.

Is it still chic to wear white sneakers with a suit?

YES | Though not the freshest trend, this remains viable in more creative or casual workplaces. “I’m a firm supporter,” said New York-based menswear designer Alexander Olch. “It does require confidence, but in my office environment I happen to be the boss.” (That said, Mr. Olch—tired of seeing men pair suits with self-consciously stylish Jack Purcells—has taken to wearing nondescript white Keds.) The key, explains branding consultant Andy Spade, a fellow Manhattanite, is head-to-toe ease: “It’s a mistake to do it with a really tailored suit.” Better to go with casual constructions by Agnès B. or A.P.C.

NO | Even for creatives, argue some, this trend is starting to look distinctly stale. And for anyone who works in a more buttoned-up office or isn’t attending a wedding in the Sonoma Valley, it remains a head-scratcher. “If you want to dress down a suit, take off the tie and swap out the blazer for a casual jacket,” suggested Altan Sadik-Khan, a client associate at J.P. Morgan Securities in New York. “If you want to wear sneakers, throw on some jeans and call it a day.”