As a rule, you should probably never wear a contrast collared shirt. No, they are never "back in style" and anyone who thinks they can be probably isn’t someone you want to be friends with in person or on any social network. The contrast collar is, in fact, a rarely effective statement garment. The statement, though, is typically "I don’t believe in tipping" or "I have a guy who does that for me." On the rare occasion that it’s pulled off brilliantly, you won’t even notice it. But American culture has come to embrace contrast collars as a red flag for personality disorders. See which category your friend or boss fits (and hope that you’re not meeting any of these criteria yourself).
The Guy Who Didn't Get Wall Street
The most legendary of contrast collar acolytes. The look is most commonly associated with power brokers and hedge fund fellows, and has been cemented in our minds with the likes of Gordon Gecko (Wall Street) and, for a jolt of diversity, Jordan Belfort (The Wolf of Wall Street). New converts wear Brooks Brothers, but we assume the presence of Brioni and a hundred other labels you would only hear these guys bragging about. Thankfully, this look has gone somewhat by the wayside (both of those films are set far enough in the past that we can comfortably call the look "period"). But unfortunately, every business school in the country can assume 65 percent of each class memorized the "Greed is Good" speech before taking the GMAT. What’s more is that Hollywood so loves this archetype that comic book villains like Obadiah Stane (Jeff Bridges in Iron Man) have been modeled from this framework. Let’s all pray there's no second coming.
The Billionaire Team Owner
Apparently when you purchase a sports team you’re issued a wardrobe of contrast collars, as if they’re some garment of pride like the equally-tacky member's jacket. Jerry Jones of the Cowboys, Bob Kraft of the Patriots, and late Yankees owner George Steinbrenner all seem to think that their pro sports purchases have made them immune to the rules of decorum. Steinbrenner may have been the worst offender, as he never seemed to throw any extra walking-around money at a tailor. It’s an industry hallmark that some team owners just look sloppy, but when you factor in the contrast collar, it’s like someone kicked over a faux-pas trashcan.
The Guy Who Thinks He’s Still in a Frat
In his mind he’s fun, but really everyone hates him. This guy ends every sentence with something like "just playing," as if it’s the cure for your sudden douchebag vertigo. He’s never had to work for anything in his life, so inconveniencing everyone around him and generally making everyone’s life awful is how he gets off. The trouble is that this fratboy prince may hide in plain sight, often in PINK. He may not even wear contrast collars every day. He’s middle management at best, like Bill Lumbergh (Office Space). Or he’s the two-faced challenger trying to smile his way into getting something you want. He understands "networking" as the ultimate game to win, though like Bradley Cooper in Wedding Crashers, he’s sometimes partial to rugby, where he achieves the look in a sporty but casual way. Possibly the worst offender on the list.
The Actual Sociopath
The problem with the sociopath is that he can be anyone, from a hotshot Manhattan yuppie like Patrick Bateman (American Psycho) to a smart and savvy politician a la Nucky Thompson (Boardwalk Empire). During the day these guys do their work, take admirable yet acceptable fashion risks, and carouse with coworkers and socialites. But after everyone else goes home, they’re out running massive organized rackets, or just stabbing bums to death in alleyways. We’d love to draw some clear and obvious connection between the contrast collar and pure, unadulterated evil, but unfortunately there haven’t been enough studies conducted by the American Psychology Association. One thing’s for sure though: If you see a lone man in a contrast collar walking toward you in a dark alley, turn and run.
Prince Charles has, over the years, made some pretty awful fashion choices in the name of the realm, or whatever. The British can and have done better, and for centuries. Even if he gets a pass on the uniforms, shoulder pads, gilded swords, and riding outfits, he still has to be held accountable to the people and to the crown for his taste for contrast collars. We’re not sure which Buckingham "Yes Man" let him walk out of the gates in this look, but we hope someone keeps him far away from the future King George so we can make steps toward ending this blight once and for all. Maybe the royal family needs more on staff than a food taster to protect them from treason.
...The Rare Exceptions
In case you were wondering, yes, there are exceptions to this rule. You may unabashedly sport contrast collars if you meet any of the following criteria: You are a member of the clergy, in which case it’s part of your uniform. Same goes for the polo shirts at Burger King, and a few other fine dining establishments. If it’s issued upon hire, you get a pass. But as Roger Moore proved during his stint as the world’s greatest secret agent, a well-dressed man can make anything work. It doesn’t hurt that James Bond killed more people than arguably anyone on this list. We’re certainly not going to question his likely Savile Row custom shirt. The whole thing is probably made of C-4 anyway, knowing MI-6. We’re happy to entertain other requests for exemption, but don’t expect much mercy.