Pocket squares are a bit like tattoos: The good ones aren’t cheap; the cheap ones aren’t good. Wearing a pocket square that came stapled to your tie is the equivalent of picking a flash tattoo off a rack. So where do you start? We turned to social media for, well, what's socially acceptable. According to Instagram, here are some rules to rocking a pocket square.
1. Be yourself. When something strikes you, let it out. Not all at once. These custom pocket squares from O’Harrow clothiers ($36) come in all kinds of patterns and monograms.
2. The plain white pocket square is still the T-shirt half of the classic T-shirt-and-jeans combo. Dress it up or dress it down. You’re in charge.
3. For the right occasion, the pocket square can do all the work. This dinner jacket by Sebastian Cruz Couture looks sick. But the usual work done by the knot in your tie is all accomplished by the red trim on this slim silk hanky.
4. Matching is overrated. “I never match anything,” says Tom Kearnan, director of global fashion and merchandising for Indochino. And he’s the expert. Kearnan is, in many cases, the person who selected the pocket squares to go along with each season of his custom suits. And he looks damn good.
5. Less is more. This beauty by MJ Bale is only vaguely in the spirit of the suit. There’s no tie to match with, but it is certainly as crisp and understated as that French cuffed shirt. This is what to wear for that networking meeting where you want to make a good impression by blending in.
6. Pocket squares are not just for suits. “Fashion represents current trends, while style more closely aligns to an individual's interests in clothing,” says dad and Instagram star Rainier Jonn (@thedressedchest). To show off his own, here he has an American-made duck canvas light jacket paired with a Kiriko pocket square.
7. Be aware of texture. Here a Sandro tweed suit is paired with a can’t-give-a-fuck American Apparel tie. But the textured look is cooled off between the plain white shirt and the grey linen pocket square.
8. When in doubt, break yourself in with something vintage. It’s like how you wanna learn stick-shift on an old beater when you’re a kid. Nobody wants to drop $200 on a silk square that doesn’t work for them when they could burn the clutch on a Saturday night on some thrift store gem they got for a buck. See how it goes. Hint: women will tell you it’s not working.
9. Get ready to get one for every birthday. When you wear pocket squares, people will start to think of you when they see them. So when you find a brand that usually works, hold on for dear life. Hugo Boss makes a couple of nice rags that you won’t mind being gifted year after year. They never wear out, they always fit and, if you don’t like them, there’s about a million stores where you can make the exchange.
10. Let the pocket square speak for you when necessary. Pair it with all black everything and let it be your statement.
11. Think of them as disposable. They fall out. Drunk people at weddings think it’s hilarious to yank it out of your jacket on the dance floor. If you really, really have the perfect matching tie and pocket square, one of them is bound to get fucked up at that same wedding. This Turnbull & Asser Dali print might be fun, but it’s still just a scrap of silk. Remember that before you drop a day’s wage on something you could lose that night.
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