pocket square in grey jacketThis page is part of our multi-page pocket square guide and deals specifically with how to wear a pocket square. We offer tips on how to pair them with ties and other articles of clothing, a bit of history, and suggestions on what squares to wear for different occasions.

Our other pages on pocket squares can be easily accessed via the following links:

You can read this entire article from start to finish or simply jump to the section that most interests you by clicking one of the links below:

Different Handkerchief / Pocket Square Folds

We’re excited to show you how to wear a pocket square with style below, but it’s important to know how to fold a pocket square properly before anything else.

You can take a look at our step-by-step guide on how to fold a pocket square where we show you six different folds you can use with the examples below.

Pocket Square Tips, Tricks, Rules, & Theory

To oversimplify, your pocket square shares the same visual plane as your tie and should coordinate with it as such. This is very important in terms of color, less so in terms of pattern. For help with pattern mixing, check out our forthcoming article on the pillars of style.

Note that we used the word “coordinate’ as opposed to “match.” This brings us to two Golden Rules as they relate to pocket squares:

  1. Pocket squares are subject to one of the only truly unbreakable rules in all of menswear: your pocket square should never, ever, ever match your tie perfectly. This looks uncreative, studied, and fussy. It also has the tendency to draw the viewer’s eye across your chest as opposed to allowing it to go upwards to your face, which is the whole point of dressing well anyway.
  2. White pocket squares go with any ensemble, any time of year, day or night, for any occasion.

In any case, we can borrow some music terminology to explain how to coordinate pocket squares and ties: the idea of major and minor.

Let’s assume your tie is red with blue stripes. Red is the major color, whereas blue is the minor color. A smart pocket square would have blue as the major color and perhaps red as the minor one.

Classic Pocket Square Combinations

With A Tie

paisley pocket square with striped tie

As we mentioned above, coordinating your handkerchief with a necktie is basically Style 101. As you don’t want to have them match exactly, keep complementary colors in mind.

Above, note the green in both the tie and pocket square.

With Suspenders

pocket square with braces

Braces share the same visual plane as the tie, which means they share the same visual plane as your pocket square, too. Solid squares tend to go well with patterned braces, and vice-versa.

With A Suit

Man in blue suit with no tie

The classic suit-and-tie combination is subject to the tie-and-square coordination rules, but if you’re going sans tie but still wearing a suit, then your world opens up nice and wide. Coordinate your square with your shirt, socks, or nothing at all.

With A Tuxedo

Wearing a pocket square with a tux is easy: keep it white, and don’t go overboard on the fold. Simple as that.

With A Sport Coat

pocket square and sport coat

Sport coats are often more boldly patterned than suit jackets, and you should feel empowered to coordinate with the colors and patterns in the coat. Note that the blue in the pocket square above picks up on the blue check of the jacket and the blue of the waistcoat.

With A Boutonniere

Boutonnieres have seen a resurgence in popularity over the past few years, and we’re delighted about this. Thankfully, they can be easily paired with pocket squares:

pocket square matched with lapel flower

The key here is to maximize your color contrast between hanky and boutonniere while maintaining some color continuity. This is because they both reside on the left side of the jacket, and you want to avoid things looking too same-same but still be connected somehow.

With A Shirt

If you’re not going to pair a square with your tie, your shirt is next in line for coordination. Thankfully, this is easy, as you just follow the guidelines about color and pattern listed above.

pocket square paired with shirt

Keeping it simple and riffing off of a combination pictured above, here we have a blue-and-white checked shirt paired with a blue-and-white handkerchief. Wearing all this with a blue jacket creates continuity, while opting for a complementary color in the lapel pin creates contrast and visual interest.

With A Bow Tie

The rules for coordinating bow ties with pocket squares is the same as it is for neckties. You don’t have to concern yourself with the bow tie’s shape or anything of that nature just color and pattern.

With A Lapel Pin

Lapel pins are similar to boutonnieres insofar as they’re worn on the left lapel and are therefore on the same side of the jacket as a pocket square. If there’s any color in your lapel pin (and there sometime’s isn’t much to speak of, as some are simply precious metals), try to contrast your handkerchief with it significantly.

With A Vest

Waistcoats are relatively uncharted territory as it relates to your pocket square. If you’re wearing an odd vest with a jacket over it, you can simply treat it as if it were a shirt when coordinating your handkerchief with it.

But, what if you’re just wearing a vest? Can you wear a pocket square too?

We say yes, if your waistcoat is single-breasted with a four-pocket front. The top left pocket can take the place of a jacket’s breast pocket, allowing you to throw a hanky in there for some extra panache.

A great rule of thumb: pocket squares that pick up on more than one piece’s colors or patterns and /or act as a “bridge” between them almost always make for smart combinations.

Wearing A Pocket Square For Specific Occasions

Wearing a pocket square will always enhance a gentleman’s attire, but it’s important to know how to wear one depending on your audience. For example, the color and fabric of your pocket square, as well as the type of fold, for a summer wedding will be far different from the one you’d wear to a funeral.

With A Tuxedo

Tuxedos generally call for solid white pocket squares with inconspicuous folds like the TV fold or a small puff fold. If you’re headed to a more lax black tie event (perhaps in someone’s home or at a social club), you can branch out from this, but keep the colors to black and white.

To Prom

If you’re headed to the prom, you’re bound by the black tie dress code mentioned above. Stick with a white pocket square, but fold it however you please.

To A Wedding

Weddings give you a lot of flexibility with regard to your handkerchief. It’s a festive occasion and your pocket square can reflect that festive spirit. This applies to grooms, best men, groomsmen, fathers of the bride and groom, and guests.

If it’s a more formal wedding, a muted pocket square with an inconspicuous fold will work. On the other hand, if the wedding is more casual, you can let some bright colors out and use a more ornate fold for added fun.

At A Funeral

blue jacket with white pocket squareYou can wear either plain white or white trimmed with black or dark blue to a funeral. The idea here is not to draw attention to yourself, but rather to look polished as a way of showing respect for the deceased and his/her family.

Keep it to a small TV fold, and be absolutely sure to keep a second one on your person. Someone near you will be crying and will surely appreciate your offer of a handkerchief.

On A Job Interview

It’s advisable to dress conservatively at job interviews. With that said, treat a job interview as you would a funeral as it relates to handkerchiefs.

Learn More About Pocket Squares

We hope you found this article as informative and enjoyable as it was for us to put it together.

If you’d like to learn more about pocket squares, check out the other in-depth resources we have below:

How To Wear A Pocket Square
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