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.  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.”  YES | “I think tailored, flat-bottom-hem shirts work well untucked in a casual setting,” said Robin Yan, a director at Bravia Capital in Hong Kong. And, of course, not all button-up shirts are dress shirts; plaids and work shirts by the likes of J. Crew and Steven Alan get a pass. Meanwhile, Alexander Olch carries dress shirts specifically designed to be left untucked—with a cropped shirttail that sits just below the waistline. Mr. Olch argued, heretically, that they look “all the more interesting” when worn with a suit and tie.  NO | Any proper dress shirt with tails is meant to be tucked in. “I actually joke about the ‘date shirt,’ which you see guys wearing untucked with bad jeans and square-toed shoes. To me, that look was out the minute it started,” Mr. Snyder said. Mr. McLaughlin, too, has no mercy when it comes to exposed shirttails. “I have this image of shirts with aggressive stripes or paisley, with these dueling patterns and interior trim and contrasting cuffs,” he said. “It’s dated. It’s a Vegas look.”  YES | Though variations on the so-called Canadian tuxedo stomped down spring runways at high-end brands from Bally to Burberry Prorsum, Mr. Spade avoids designer labels when wearing denim head-to-toe, a look he endorses: “An old Levi’s 501 with a desert boot and a great chambray shirt—I’m in advertising, and I’d wear that to work.” Chambray—resembling denim, but more simply and finely woven—can upgrade such an ensemble. (J. Crew offers its popular Ludlow suit in it). In most offices, of course, neither is appropriate, especially if combined. “But for weekends, absolutely,” said Christian Conroy, who works in client relations at UNFCU Advisors in New York. “My rule is that the denim should be contrasting colors.”  NO | A solid pair of jeans has a timeless appeal, but the blue-collar pretension of denim-on-denim is as laughable now as it’s ever been, said Mr. McLaughlin: “It only works if you’re Chuck Norris.” Added Brian Valle, financial officer at a real-estate development firm in Washington, D.C.: “Or if I happen to be performing some sort of ranching function.” That the trend is big in this spring’s collections doesn’t mean much, Mr. Snyder said: “One out of 10 guys at best can pull off this look without looking like he’s working on the railroad—so, if you’re even asking this question, the answer should be no.”  YES | Supposedly a casual look, stubble inevitably seems fussy and premeditated these days, argued Mr. McLaughlin. “It’s always a fashion statement, [so] it looks a little foolish to me,” he said. “It implies ruggedness, but when you think that the person worked hard to get this—he had a special razor and rigged it all up—there’s nothing natural about it.” Now that a generation of men has rediscovered the badger brush and hot-towel shave, why not enjoy the clean-shaven look?  NO | “I don’t think stubble is ever going to go away,” said Jeff Laub, founder of the shaving brand Blind Barber, based in New York. “It comes across as a sign of masculinity.” The trick, Mr. Snyder added, is to keep one’s stubble looking at least plausibly natural. (See Bradley Cooper.) “You don’t want constant stubble, or a shave line under the neck—that to me is a big no-no.” Stubble is particularly defensible when it comes to men who lack hair up top. “It gives you some coverage, so you don’t look like Mr. Clean,” Mr. Spade said.  STYLISH | “Loafers are more appropriately worn without socks,” said Michael Andrews, CEO of the New York tailor shop Michael Andrews Bespoke. (He doesn’t bother wearing loafers in winter.) Worried about the smell? “Don’t do it multiple days in a row,” he added. The look’s potential to raise eyebrows is part of the point. “Girls like it,” claimed Page Leidy, a principal at a real-estate investment company in New York. That is, assuming you do it correctly, said Mr. Spade: “You need the right shoe, like a classic Alden loafer, and you have to wear it with a pant that’s tapered and not too long.”  UNCOUTH | Newly common in some workplaces, bare ankles have provoked backlash lately, on both hygienic and aesthetic grounds. “lately. “I find the sockless thing a bit contrived at this stage, particularly with that heavy brogue or wingtip,” Mr. McLaughin said. The look is impractical, said Mr. Snyder: “If you want to keep a shoe for a long period of time, this is the wrong way to do it—and there’s no way to get the stink out.” For determined ankle exhibitionists, no-show socks—like Peds, which sit below the ankle line—help on the hygiene front.  YES | Rolled pant legs have become boringly ubiquitous, some argue. Since when is it déclassé to wear chinos that are already the correct length? “This trend has gone way too far,” Mr. Sadik-Khan said. “Hemming pants is not some enormous financial burden. If you can’t find a decent tailor, just take them to your cleaners.” What began as an easygoing fix has become transparently faddish, said Mr. Spade: “If you’re in Nantucket, sure, roll them up. But the conscious rolling thing looks a little bit too thought out.”  NO | Relax, people. Chinos are a casual trouser, always have been, and are not meant to be taken too seriously. Rolling is an especially nice flourish if it reveals a new detail, said Mr. Valle: “With pants with interesting seams or linings, like Bonobos, I can see the appeal of rolling for a pop of color.” Mr. Andrews added: “I’d much rather have rolled chinos than a tapered sweat pant, which we’re seeing a lot of now.” Still, this gesture derails when it comes to perfectly tailored pairs, said Mr. McLaughlin: “I would say rolling looks better on an ill-fitting pair of chinos, with a wider leg. You’ve got to get it a little wrong to get it right.”  YES | The juxtaposition of refined and relaxed is what makes this look interesting. And, in some cases, said Mr. Olch, it’s even functional: “On a hot day where the first thing you say to yourself is, ‘OK, I’m wearing shorts,’ a jacket can serve you well.” Approach this combo as a way to dress up shorts—slim, tailored shorts that end just above the knee—rather than dressing down a jacket. Mr. McLaughlin said that patterned shorts “look particularly good right now with a blazer.” Even he, though, would concede that this trend is better suited to younger men.  NO | All-seasons formal on top, summer casual on bottom? The disconnect simply defies logic. Leave this bratty look to style pros like Pharrell Williams, who’s just about the only guy who can make it work. “Perfectly appropriate in Bermuda. Otherwise, it makes men look silly,” Mr. Andrews concluded. “Better to just go with rolled chinos,” Mr. Yan advised. “Jeans and a blazer, I get,” Mr. Valle said. “But shorts just seem so casual. And if I’m wearing shorts, that means it’s hot out, and so the last thing I’d want to do is wear a blazer.”  DEFINITELY | Who cares if stores are already pushing shorts and polo shirts and—in certain quarters—fishnet tank tops? “The second Arctic-chill-vortex has definitely jaded me into thinking it’s way too early to talk about spring,” Mr. Snyder said. “All I can think about is how to stay warm.”  NAH! | For Mr. Andrews, whose company requires eight weeks to make its bespoke clothes, customers with early-onset spring fever are welcome. As for the ready-to-wear buyer, Mr. Valle said, it’s never too early for escapism. “In winter, we pine for spring. And fashion has always been aspirational.”  Sources: Søren Jepsen (2), Getty Images (6), Trunk Archive (2), Illustration by Michael Hoeweler (4)
Torn between the urge to up your style this spring, and the appeal of playing it safe? We asked a panel of fashion experts—and some dapper guys—for verdicts on seven controversial trends, from the sockless look to suspiciously well-groomed stubble. Bonus: Cast your votes in our online poll.