As the Federal Bikini Inspector t-shirt reminds us, a man’s clothes say something about him, but it’s not always what he thinks. Fashion is a conversation. Like any conversation, the nuances can be hard to make out. One solution to this problem is to wear clothes that say as much as possible—shirts with skulls and wings on them, big colorful Nikes, jeans abraded with wire brushes by Indonesian children—in the hopes that you will randomly make an interesting statement.
While this approach is popular, it’s also like shouting out the names of various cheeses and sex acts and hoping that you’re speaking French. A better option may be to speak a little more quietly and know a little better what you’re talking about. With that in mind, plaid is a great way to start the conversation.
Historically, no fashion mainstay has said as much as plaid. In 1746, when Britain wanted to bring the warrior clans of Scotland under tighter control and maybe get them to stop decapitating landlords every Sunday, they passed the Dress Act, banning plaid. England knew what it was doing. While contemporary plaids might not tell us which highland region the wearer comes from, they still say plenty.
Consider the two plaid shirts above. One is a little bit J. Crew, while the other is a little bit J. Mascis. Nuances, here, contribute to a difference that most of us intuitively recognize—a narrow pattern makes the plaid on the left more preppy, while wide stripes and eighties-only combination of purple and black in the plaid on the right make it a staple of contemporary hipsterism.
Chances are, neither “preppy” nor “hipster” is something you want to say to people. The beauty of plaid is that the differences among patterns are ones of degree, which makes it extremely versatile. That means you can integrate plaid into your wardrobe without spending a lot of money or risking too much of your reputation as a man who doesn’t think about clothes.
Zero risk: the plaid tie
Even if you aren’t known fop Justin Timberlake, you can still use a plaid tie to brighten up an otherwise conservative ensemble. Chicago neckmongers The Tie Bar sell an array of 100% silk plaid ties for $15 apiece, which means you can add two to your arsenal without becoming the Tie Guy or the Broke Guy.
Choose a small-pattern, monocolor check to wear with dark suits on Monday and a more colorful tartan to wear with jeans on Friday night. Strange women in bars like a man wearing a tie; it gives them something to make fun of at first and something to pull on later. Don’t let your new tie convince you that it’s okay to wear a vest.
A little braver: the gingham shirt
Gingham is not technically plaid, in the same way that correcting people is not technically conversation. It’s a classically American pattern that draws the eye and, if you’re not careful, makes it twitch a little. The trick to wearing gingham is to pair it with rich colors—dark jeans, navy jackets and—as long as your shirt isn’t a western cut—charcoal suits. Gingham is a mainstay of 1970s fashion, which means you can get vintage gingham shirts fairly cheaply. The one above retails for $28 at VintageTrends.com.
Gutsy: plaid pants
Unless you are a professional golfer or the creator of a mathematics-themed magic act, you want to be careful about how many colors your pants are. Still, in certain situations—going to brunch, betting on horses, or posing for a Seurat painting—a pair of plaid pants will take you from mark to rake. Make sure the legs are narrow—baggy plaid pants are more commonly known as pajamas—and stick to grays, or tans, beiges, taupes and other euphemisms for brown. International law requires that you wear plaid pants with a white button-down shirt, and only with a white button-down shirt. You’ve given people plenty to look at already.
Impossible for you: the plaid jacket
Are you the Duke of Windsor? Did you poach quail eggs for breakfast? Take that off.
Dan Brooks writes about politics, consumer culture and lying at Combat!