Pocket Square Basics: How to Wear One, Three Ways

ByPeter Joeseph 'Briefcase Maker' Kalafatis

Strip away the folds and a pocket square is a hemmed square of cloth with a pocket to live in. Its first job was wiping a face or a hand. Its job now is to give a jacket one small, deliberate detail, and three folds cover nearly every room a man walks into wearing one. A single rule about color covers the rest.

Start with the square, not the fold

Size decides more than technique does. Bespoke Unit’s guide puts the most versatile silk squares at about 16 to 18 inches, enough cloth to hold volume instead of sliding down into the pocket. Cotton handkerchiefs run smaller, roughly 9 to 12 inches, and an oversized one bulks up the chest. Equal sides matter. A rectangle is awkward to fold and never sits right.

Fabric works by contrast. The same guide offers a rule that fits on a card: “The smoother the jacket, the rougher the pocket square!” Silk against tweed, flannel or Donegal looks deliberate. Silk against a glossy suit looks like one fabric printed twice. Cotton and linen sit comfortably in worsted wool and cotton jackets, and linen suits warm weather best.

The mistakes the guide implies are worth listing, because they are the ones men make. Going without a square altogether when wearing a tailored coat. Choosing one too small to hold its shape, or too large to sit neatly in the pocket. Pairing a smooth square with a smooth jacket, which loses the contrast that makes the look work. Using a silk square as an actual handkerchief.

Two warnings from the same source. Some squares sold as silk are polyester, so read the label. And hand-rolled edges are not required; a machine-sewn edge is fine if the square is large enough and the cloth decent.

The flat fold, for rooms that are serious

The flat fold goes by several names, and “presidential” is the most common. Eton’s guide calls it the most formal option, and Real Men Real Style recommends it when formality counts most.

Hands folding a white linen pocket square

Lay the square flat. Fold it in half, then in half again, until the band is about as wide as the pocket. Tuck it in so one straight edge shows above the pocket line. That is the whole fold.

Gentleman’s Gazette calls this family the TV fold and pairs it with white linen and a hand-rolled edge. John Burton, writing for Ivy Style, describes a plain white linen square in a simple fold under a navy or gray suit as the version that never feels overdone. It belongs in a courtroom, an interview, a funeral, any room where nobody should look twice.

The puff, for rooms that are not

The puff takes ten seconds and forgives almost everything. Pinch the square at its center and lift. Let the edges fall into a loose tube, then drop the gathered end into the pocket so the rounded top shows. Some wrinkling is part of the look; Real Men Real Style files the puff under stylish and relaxed rather than formal, and Eton calls it the most versatile fold, with the height of the puff adjustable to the outfit.

Soft silk and cotton do this best. A stiff, starched square wants a sharper fold. Burton’s line on the subject is hard to improve: “pocket squares are like first kisses, never a good idea if they feel forced.” A puff that looks windblown reads as confident. One that has been pinned and sculpted reads as effort.

One point, for everything in between

If a man learns only one fold, the one-point is the candidate. Fold the square into a triangle. Fold the side corners in toward the middle to make an envelope shape. Tuck the base into the pocket so a single point rises. Real Men Real Style lists it as working with business suits and relaxed blazers alike, and The Art of Manliness names a one-corner fold as its favorite of three it demonstrates.

Past those three, the field gets showier. Real Men Real Style catalogs a two-point and three-point fold, the four-point named for Cagney, the scallop common at weddings, and the Dunaway, which gathers the cloth into a fringed, flower-like tube. The four-point does best in thin, stiff fabric such as starched linen. The scallop wants a glossy, colorful square. Most men will never need any of them. Learn the three above and the rest are variations on a theme.

The Art of Manliness demonstrates the straight, one-corner and puff folds (YouTube).

A wedding adds a second small flower to the jacket. Gentleman’s Gazette has a short video on wearing a boutonniere correctly, and its page advises that a lapel flower can sit alongside a pocket square only if the lapel has a buttonhole.

Gentleman’s Gazette on wearing a boutonniere and lapel flower (YouTube).

Coordinate with the tie. Do not copy it.

Here the advice stops being about cloth. Match the square to the tie exactly and the pair reads as a set that arrived in one box. The Art of Manliness says exact color matching “looks like you’re trying too hard,” and suggests pulling one color from the tie into the square, or going solid. A white square works with any tie. Pre-matched tie-and-square sets get the same verdict.

Three pocket square folds on a dark walnut surface

A. C. Phillips, who wrote The Pocket Square: 22 Essential Folds, adds the other half of the rule. A review in the New York Journal of Books quotes his advice to keep a square for display apart from one for use: “one square for show and another to blow.”

Evening wear tightens the rule instead of loosening it. For a black-and-white outfit, Gentleman’s Gazette suggests a solid color such as red or purple as the accent, and cautions that a patterned square can take away from the elegance of a tuxedo. Solids are the safer choice whenever the dress code gets stricter.

Current trend writing points the same way. A Beau Ties blog post describes muted shades such as off-white, soft blue and muted green, looser folds, and squares worn without a tie, over open collars or knitwear. With no tie to match, the rule gets easier, not harder.

Why it came back

Richard II of England is credited with popularizing the cloth handkerchief in the late 1300s, according to Wikipedia’s entry. By the early 1900s, The Art of Manliness reports, a well-dressed man did not leave home without one in the breast pocket, and by the second half of the century the habit had faded alongside the hat. Studio Suits credits Cary Grant and Gary Cooper with putting the look on screen. Wikipedia notes that folds were later named for Cooper, James Cagney and Fred Astaire, and that Mad Men helped revive the square in the late 2000s.

A 2013 Pittsburgh Tribune-Review story, reprinted by the Philadelphia Inquirer, offered a second cause. Clothier Joseph Orlando Jr. tied the comeback to men wearing ties less, since the tie had been where personal style lived. His peer Tom Michael of Larrimor’s gave the short version: “It takes a suit to a new level.”

Squares and a reference worth owning

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Start with the flat fold, in white. Wear it three times. Then try a puff on a Friday and see who notices. The same restraint applies to the case that goes with the jacket, a point made in The Leather Briefcase: A Symbol of Professionalism and Style.

Man in a gray flannel jacket with a puffed silk pocket square carrying a leather briefcase

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