After years in popular dormancy, mid-century inspiration from shows like Mad Men brought pocket squares back with a vengeance. Since then, their popularity only seems to be accelerating.
Recently a menswear shop sales associate commented to me he sells more pocket squares than ties these days. As our public dress become more casual, it actually makes a little sense that someone who likes wearing a tailored jacket might want to make a pocket square the accessory that adds a dash of color to their ensemble rather than a tie. And there are benefits to doing so. For one, a square can be vastly more colorful and complex than a tie and still be within the realm of good taste. For another, they’re less expensive to buy and smaller and easier to store.
Here are a few tips for how to wear a pocket square well, with or without a tie.
1. Easiest and most classic pocket square: the white linen “TV fold”
The classiest way to wear a pocket square is to get one made of simple white linen, and to fold it up in half or thirds until it fits into your breast pocket. This is popularly called the TV fold because TV hosts from the mid 20th century wore pocket squares this way. It looks good with dark jackets like navy or charcoal, in particular. Because of its association with dark suits, it has a bit more formal connotations, and therefore I do not wear it with casual jackets, like tweed gun clubs or other checks.
Some like to make complex origami-esque folds, with the corners of the square pointing up out of the pocket. For instance, Joe Biden—the first U.S. president since Ronald Reagan to wear a pocket square—has been photographed doing this. In my early days of wearing pocket squares, I used to do these types of folds, but I settled into the simpler TV fold over time and that’s my recommendation for most folks (but don’t let me steal your origami fold joy!).
My white linen pocket square is from J.Crew, and it’s easy to move from one jacket to another. However, if you bought a multi-pack that might be convenient.
Shop: White linen pocket squares
Kent Wang white linen pocket square
Drake’s white linen pocket square 3-pack
J.Crew white linen pocket square
Brooks Brothers white linen pocket squares
2. Choosing the right pocket square colors
The biggest faux-pas to avoid when wearing a pocket square is: do not match it with your tie. Do you think those rental tuxedos with the cummerbund and tie in a neon color matching your date’s dress show good taste? Of course they don’t. That’s the equivalent of matching your tie and pocket square. It is cheesy and lacks imagination. I would rather see no pocket square than one made of the same fabric as the tie.
Pocket squares should complement your tie. That’s easier said than done well, but you can learn to do it. The basic principles are the same as with any other use of color. Go read my post Learning to Use Color and Contrast to learn more on that.
If you aren’t wearing a tie, you have much more leeway. In that case you only have your shirt and jacket to think about. Many squares will have multiple colors, so a different color will come out depending on how you stuff it in your pocket. As long as it doesn’t clash with your jacket’s color or pattern, you’re set.
Shop: Drake’s pocket square selections
3. How to choose pocket square patterns
This is where the pocket square shines. You can wear literal works of art in your breast pocket. In fact this is my preference for pocket squares. They often have a broad palette of colors, meaning you can pair them with a wider range of jackets. Another benefit is that they turn completely abstract when stuffed in the pocket, so there are no discernible patterns that might either draw additional attention or create a clash with your shirt or jacket. Plus I just think it’s cool to have this secret work of art that nobody knows about because they only see the slivers of color and pattern poking out.
If artwork seems a little wild for you, repeating patterns like paisleys or geometric patterns like dots are just fine, too. Just remember the rule for pairing patterns together: make sure they’re not too close in scale. (So if you have a striped jacket on where the stripes are 3/4” apart, don’t wear a pocket square with a pattern around that same scale; go big or go small).
You can also go plain. Besides the plain white linen mentioned above, solid colors can also add a simple, elegant flash of color to your outfit. I had a tan gun club sportcoat years ago, and the best pocket square for it was a simple plain silk one in cream. It worked so well on a couple different levels: texturally the soft, smooth silk contrasted well with the rougher tweed-like texture of the jacket; and the lack of pattern was a little respite from the busy gun club.
Shop: Kent Wang’s pocket squares in great works of art
4. Pocket square textures and fabrics
The most common fabrics for pocket squares are linen and silk; linen usually for the simple white square, and silk for the colorful, more expressive ones. These days you’ll find colorful and expressive prints on linen, too, however, as well as on cotton or wool. Here’s my recommendation for how to choose the right texture for your pocket square:
I usually prefer matte squares because they’re a little less flashy than the sheen of silk. My default is cotton, wool or linen for this reason. However, a textured jacket like tweed or flannel is often best complemented by a smooth silk square. Just like how wearing a smooth broadcloth shirt with a fuzzy flannel jacket is appealing for its contrast in textures, so too can your pocket square give your outfit some nice contrast.
The body of each fabric also changes how it looks in your pocket. Silk tends to have much less body than the other fabrics, so it flattens more easily when you stuff it in your pocket. Linen, cotton and wool are all bulkier, though how loosely woven the fabric is and how big the pocket square is will mitigate that some. So I have no specific recommendation of which fabric is best; that will depend on your own taste.
Shop: Mr. Porter’s selection of pocket squares
5. How to stuff a pocket square in your pocket
With a white linen TV fold, it’s simple: fold it in half or sometimes thirds until it’s roughly the same width as your breast pocket, then fold it in half long-way and put it in your pocket, adjusting the length until it pokes out the top. Easy.
With every other type of square, there is a specific technique, enumerated in the series of photos from Rubinacci below that is the One Way I think you should do it. Basically, pinch it in the middle of the square, grasp it loosely with your other hand to gather the four corners all together, then fold the whole thing roughly in half and stuff it in your pocket with the corners and center both popping out. OR do that same exact thing but put it in upside down—with the corners and center pointed down, allowing a round poof to show. You can adjust it to show different parts of the square to bring out different colors.
So that’s how to wear a pocket square. While there’s still nothing better than jacket and tie, in the increasingly casual world we live in, use a pocket square to add some visual interest to your tailored outfits. It’s a fun way to introduce color and texture to your outfit.
If you have a nice little collection of pocket squares and want a cool way to store them, check out Dapper Woodworks, who makes high-quality tie and pocket square storage racks. I wrote a review of the tie rack 2 years ago and I’m still smitten with it. Get 10% off your order with my discount code, MM10.
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