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Pocket Square Appreciation

April 6th, 2017


A pocket square, a handkerchief, a hank, a flourish; call them what you will, their status in the modern gentleman’s wardrobe is assured.

Some have worn a pocket square for years, influenced by the artistry of grand old stars of the silver screen like Clark Gable and Fred Astaire, who were rarely photographed without one. They are generally quite useless, as few gentlemen would hand a prized silk square to a tearful lady obscured by mascara, although they can be used as a secondary lens or screen wipe.

So, although not strictly functional, a pocket square is aesthetically brilliant. When you begin to wear them, they look and feel odd. You will find yourself fiddling with them, straightening them, puffing them, overtly conscious of their presence in your top suit pocket; this period is awkward and slightly inelegant but it is simply one of the uncomfortable ‘initiations’ men are required to bear.


After becoming accustomed to this decoration, your pockets (and those of others), will look naked without it. You will graduate from the freshman plain white to sophomoric patterns like polka dots and unusual colours like burnt orange leading you to pursue, continually, the extraordinary; unusual checks and paisley are clear signs of a pocket square veteran.

Seasonal Combinations

The really pocket-conscious gentleman will not only cleverly match or tastefully contrast a pocket square to the rest of his ensemble but will also dress his pocket according to the season. A dark plum silk worn with a birdseye navy suit is a classic autumn/winter combination, whereas a light pink silk worn with a khaki cotton suit is distinctly summertime.

Pastel colours are perfect for wearing with lighter suits as they do not ‘interrupt’ the suit too vividly. For the same reason, deeper tones are preferred with darker suits. If wearing a darker jacket in summertime, perhaps with an odd pair of linen trousers, it might be an idea to match a lighter square to the trousers or the shirt.


The Material Issue

Everyone thinks of silk when they think of pocket squares, despite the fact that most of the hanks stuffed in pockets of old were plain white cotton. Silk is certainly a beautiful fabric; perfect for stuffing and the lustrous qualities for catching the eye. However, considering the plethora of silk ties and ‘suits of a certain sheen’, adding another shiny bauble to an ensemble is often excessive. A lovely cotton or linen square, stuffed or folded into the top pocket, is the perfect foil; the importance of texture difference is one of the most underrated considerations of a gentleman’s attire.

By Winston Chesterfield

Browse our Pocket Square Collection

More –

Style Guide – Why a Knitted Tie
Style Guide – Belt and Braces
Style Guide – Socks