Jay Arem and business partner Jack Fischman founded their men’s accessory line, the Knottery, over a shared love of telling jokes and menswear. Their designs include ties, belts, and that oldie-but goodie: pocket squares. “When I was wearing a pocket square eight years ago, my friends would look at me like I was crazy,” Arem said. The pocket square, developed originally as a handkerchief during Grecian times, “isn’t functional. I mean, I wasn’t wiping a woman’s tears with it.” He paused. “Not that I go around making women cry.”
But, Arem notes, it’s all about details, and that’s where the pocket square comes in. Disposable tissues may have replaced cloth handkerchiefs for everyday use, but “We’re in a post-Casual Friday world. We have a culture of being fit and healthy, and the next logical jump is to start caring about the way you look, too.”
Patrick Ryan and Miriam Zelinsky started Lazy Jack Press to bring a bit more personality into menswear. “Pocket squares for us are a nice complement to the ties, because some people just don’t wear ties ever,” said Ryan. “For a regular guy, a pocket square is a place where you can express yourself in lieu of a tie.”
Pocket squares are for women, too. “I wore one of our pocket squares for a trade show we did last week,” said Zelinsky. “It looked really jaunty, and just as good as it would on a guy.” Her partner agreed. “I think it looked good,” said Ryan. “I think she should do it more.”
The texture of the fabric is every bit as important as the color and pattern. The polished gleam of printed silk, for example, makes it an excellent choice for formal occasions, and its smooth hand also makes it perfect for some of the jauntier, more casual folds. “I change it up, depending on my aesthetic,” said Aren. “A silk paisley one if I’m feeling dressy, or for work I’ll wear a linen handkerchief. I personally own over 50 pocket squares.”
The crisp lines of cotton and linen make tidy businesslike folds look clean and well put together. Linen’s coarser texture is nicely shown off against a blazer with a smooth fabric.
“It really depends on the rest of the outfit,” said Ryan. “You know, mixing of texture is a huge thing right now. If you’re wearing a knit wool tie, you can play with texture along with your pocket square. You might wear a pocket square of a lighter silk and that’s a nice balance.”
“My personal preference is a cotton pocket square,” said Arem. “If it’s plain, it’s a simple way to match it up. It can also be fun to get something a little more seasonal, like linen for summer or wool for winter.”
“The gateway drug of pocket squares is the white pocket square,” said Arem. “It goes with anything, it’s easy to wear.” Wearing a pocket square without a tie is a casual way to start, since when you add a tie matching becomes a bit more complicated. But it’s not so hard as it seems, said Aren. “Don’t worry about it so much. Just try to keep the color families the same.”
A pocket square should complement the tie, added Ryan. “It should pick up a color that’s in your tie and also bring in maybe another color or another texture. Let’s say you’re wearing a woven cloth tie with a navy ground and gold crests. You could wear a gold pocket square that has some sort of subtle print on it.” Using the pocket square to bring out the detail of your blazer is also a good strategy. “I’m wearing a blazer right now with gold buttons, and our pocket square which has gold undertones,” said Ryan.
When in doubt, a neutral color like gray, cream, or classic white are always a good choice for a clean and businesslike look. One last note: keep in mind that a rolled hem gives a classier look than a folded one.
How you fold your pocket square is up to you. Experiment until you find a signature style, like Patrick Ryan. “The way I like to wear a pocket square, it looks sort of like a beluga whale and a tail, with the tail being the end of the pocket square.” Here are a few basic folds to get you started.
The Flat (or Straight) Fold
Despite its simplicity, this sharp fold means serious business and understated sophistication.
Fold your pocket square so it’s the exact width of your breast pocket (rather than just in quarters), then fold up the bottom so the total height is no more than 1/2″ longer than the pocket. Tuck it into your pocket so just a sliver is showing.
Neatness and crisp lines are the hallmark of this group of folds, which are best suited to cotton or linen pocket squares. Keep in mind that the more points you add, the more formal the look. One- and two-point folds look smart for business occasions, whereas crisp three- and four-point folds up your outfit’s level of sophistication.
The One-Point Fold
Fold your pocket square down to about a 4 1/2″ square. Fold that square into a triangle, then fold the acute-angle ends in so it’s the width of your breast pocket.
The Two-Point Fold
Similar to above, fold your pocket square down to about a 4 1/2″ square. Now turn it 45 degrees so that it looks like a diamond with the folded edge on the lower right, then shift the layers so the points at top are offset by about 1/2″. Fold in the other three points so it fits in your pocket.
The Three-Point Fold
Fold your pocket square into a triangle, then fold both side points up and over to make a tulip-like design. Fold up the bottom behind your design, then tuck it into your pocket. To make the Four-Point Fold, simply offset the two upper points in the first step.
Puff and Reverse Puff Folds
Both the Puff and the Reverse Puff folds produce a softer, more pillow-like structure that shows off luminous printed silk pocket squares perfectly.
The Puff says you’re well-dressed, but relaxed. To create it, simply grasp your pocket square by the middle, letting the points hang down. Pinch it off about halfway down, and fold up the hanging points so it fits in your pocket. Adjust the puff as desired.
The Reverse Puff is the exact same, but instead of the center of the pocket square peeking out, insert it upside down so the hanging points peek out of your pocket like petals.
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