How to Wear a Pocket Square

by Welcome to Outsons

Not quite aware of the importance of the pocket square? This small but mighty fashion accessory is often overlooked, but here we tell you why it’s a little gem that deserves a place in every man’s wardrobe.

Let’s be honest, the first items you’ll usually think of when looking to elevate your outfit are probably key pieces such as a classic timepiece, the latest man-bag or a baseball cap; surprisingly, one major missing piece that often gets overlooked is the humble pocket square.

This pocket square is currently having a sartorial renaissance as one of the single most indispensable tools for defining a man of style. It isn’t just a fiddly bit of fabric, or a posh piece of cloth fit only for the upper classes; but a hard working wonder which can add serious panache to your look without seeming too try-hard.

It also allows the opportunity for you to express your personality at times when you would otherwise be uniformed. In order to take your look from zero to hero in seconds, we’ll answer your questions and arm you with all the info you need to fold a pocket square like a pro.

Whilst the basic rules of suiting are relatively widely known, the addition of a pocket square is often overlooked. With fabrics and folds aplenty, there are many ways to wear a pocket square depending on the look or feel you want to express, and we have a fold to suit every mood.

Need a little more convincing? Check out this video with some reasons why you should be sporting a pocket square.

What to Consider


If you are a beginner, solid colours are the simplest option as you don’t have to worry too much about matching your square to the rest of your outfit; both white and blue tend to be easy to tie in with almost anything.

If in doubt, opt for other subtle, muted shades such as greys and pinks as they will also go with most looks. Beginning to feel a little more adventurous? Go for contrasting edges before going all out and experimenting with a pattern such as gingham or polka dot.

Photo Credit: Pinterest | SHOP: Suits, Accessories


Essentially, any fabric can be used as a pocket square as long it is thin enough to fit in to the breast pocket without bulging out and looking clumsy; however silk, linen, cotton and wool are the most favoured cloths for the job.

  • Silk: The most luxurious of fabrics when it comes to the pocket square, and usually the most hard-working too, as it is perfect year-round. A silk square is versatile, making experimenting with various folds easy and is the only option when it comes to black tie.
  • Linen/Cotton: These more casual fabrics should generally be worn in spring/summer, however, if you live in a hot climate they are acceptable all year round. These cloths require a more simple fold.
  • Wool/Cashmere: Along with flannel and tweed, these fabrics should be reserved for the colder winter months.


How you fold your square can make all the difference, as they have the ability to dress your outfit both up and down, and can portray whatever look it is that you’re wanting.

  • Square or Straight: A square fold is the easiest and most popular, working best with both cotton and linen fabrics. This fold is also the best option for a professional vibe, making it a perfect edition to your work wear, and propelling you from boring business to effortless elegance in an instant. Folding this way in a white silk fabric would make great black tie attire.
  • One Corner/Tip: This fold does exactly what it says on the tin. Suiting any type of pocket square or dress code, this is a great go-to for all occasions and especially good for the amateur folder. For best results choose a solid coloured square, avoiding white.
  • Two Tip/Peak: Fancy something a bit different? This fold adds a little more interest to your look and is perfect with patterned fabrics to accentuate the uniqueness of the look. Wear this fold when opting for a smart-casual look; something sophisticated rather than formal.
  • Puff: The most casual of all the the folds, this one is great for a relaxed look that doesn’t look too try-hard. A silk or wool square is key here, and any pattern is extremely welcome- think paisley and tartan.

How to Fold a Pocket Square

You could have the most elaborate, stylish selection of pocket squares in the world, but if you don’t know how to fold them properly – they’re about as useful as a pack of kleenex.

While the perfect fold is a debatable topic, typically if your opting to wear a pocket square it’s safe to say your not the shrinking violet type. The Aficionado fold is one of the more elaborate, but impressive ways to fold your pocket square. Follow the steps below to add the aficionado flourish to your suit jacket.

  1. Place your pocket square on a flat surface.
  2. Fold one side upwards on top of the other while still allowing the tip of the underside to peek out.
  3. Next, fold one side in to create the third tip – as seen in the image below.
  4. Fold the opposite side in the same way as you did in step 3.
  5. Place the pocket square in your pocket, and you’re done!


How to Wear a Pocket Square

So now you’re armed with all the folding know-how, and you’ve picked your favourite colours, are you confident enough to put your new-found knowledge to the test?

If you’re still a little unsure, then fear not! We have compiled a look book packed full of outfit ideas to make sure you’re the most dapper of the bunch.

Pocket Squares for Black Tie

If you’re lucky enough to have a formal event to go to, then you want to stand out for all the right reasons. Black tie deserves nothing less than silk in your pocket, no matter what style you have chosen.

If you opt for classic black, then we would always suggest keeping it simple with a white square. Patent lace-ups are the best option when it comes to footwear – and let’s be honest, when else can you pull them off?

If suave is your middle name, then a deep and rich midnight blue is your game. Sophisticated gents the world over are huge fans of this hue for their formal wear, and we would suggest sticking with a basic white square here too. There’s a lot to be said for respecting tradition!


Pocket Squares for Business Attire

Formal business dress can often scream boring, and no one wants to be called boring. Perk up your office ensembles with a mix of pocket squares to suit every day of the week.

Start as you mean to go on with a bold, solid colour on Monday then kick up the experimental mode a notch as the week progresses. Standard grey and navy suits instantly exude confidence when a pocket square is added.

Friday you’ll be partying, will you not? Let your pocket square tell everyone that. Adding in this accessory allows you to portray some personality without having to buy a wardrobe full of different suits, whilst still managing to stay well within the confines of how business dress should look.


Pocket Squares for Casual Clothing

Worn in the right way, a pocket square can transform your look in an instant and be a true sign of a well-dressed gentleman, adding elegance and style to even your casual wear.

Denim works well in this instance, and teamed with a well-fitting blazer, a basic tee, and a smart shoe (such as a brogue), this combination is a true winner. A chino does the same job but with a slightly smarter feel than jeans; something like a black chino, white shirt and stone blazer with a polka dot pocket square is ideal for a Saturday night on the town.


Pocket Squares for a Three-Piece Suit

A staple of London fashion, the three-piece suit is part of our sartorial heritage, and in no uncertain terms, a real head turner. If you’ve ever worn one before you’ll know what we mean, as you are sure to have had more flirty glances headed in your direction than ever before.

What’s great about this look, is the ability to remove your outer jacket and still look super smart. The best part it – a waistcoat or vest can rock a pocket square just as good as your average blazer.

If you’re wearing it alone, you can definitely wear a pocket square in a vest and still look cool, however shirts with pocket squares are a definite no-no, and a dress shirt with a pocket square is even worse.


We spoke to William Skinner, Managing Director of Savile Row tailor Dege & Skinner, and he gave us some great tips on all things pocket square:

There are many ways of wearing a pocket square. It’s a very individual choice and an easy way to portray a little of your character.Personally, if I forget to put one in in the morning then I feel under dressed. It would be nice to see more people wearing them.

 – William Skinner, Managing Director of Dege & Skinner

Pocket Square Rules

Yes, it’s totally about personal style, but we still suggest sticking to these pocket square rules to get it on the money:

  • A pocket square should always complement your shirt and tie but never match them exactly.
  • Texture matters: a white silk is oh-so-different to a white linen.
  • Make sure it is always, always clean and pressed.
  • Never put a pocket square in a shirt pocket.
  • They are not meant for your nose. Always carry “one for show and one to blow”.
  • Just like most things in life, if it’s bulging enough to draw the eye then you probably need to rethink the size.
  • Don’t overthink it – most squares will take on the personality of what you’re wearing and will work with almost all your looks.

Can You Wear a Pocket Square in a Shirt?

We could go into some elaborate story here about the argument for and against wearing a pocket square in your shirt, but the simple answer is – no.


Still not totally convinced? Take a scroll through our gallery of celebs who rock the pocket square look.

David Gandy

True pocket square connoisseur, male model, and Mr Mollie King (are they/aren’t they?), David Gandy knows where it’s at in the dapper department, with his look never less than perfect.

Whether he’s going all out three-piece formal wear or laid back t-shirt and blazer look, D.G. doesn’t leave the house without his trusted hanky close to his chest. This guy can do no wrong in our eyes, and he’s your go-to guy for inspiration on any pocket square look.

Photo Credit: Pinterest | SHOP: Suits, Accessories

Johannes Huebl

One half of the ultimate stylish couple (#couplegoals all day long), German model Johannes Huebl knows the importance of the pocket square; even making sure he was armed with one on the most important day of his life when he married long time love Olivia Palermo in 2014.

Photo Credit: Pinterest | SHOP: Suits, Accessories

Daniel Craig

If Bond himself dons one, then I doubt you need much more convincing than that! Channel secret agent chic like Daniel Craig, and forgo the tie for a more relaxed, open collar look.

Photo Credit: Pinterest | SHOP: Suits, Accessories

David Beckham

Dedicated follower of fashion and dad of four David Beckham is the ultimate man. Period. If he’s doing it, we’re in!

Photo Credit: Pinterest | SHOP: Suits, Shoes

Thanks to the like of Dermot O’Leary, David Gandy and Tinie Tempah, the Pocket Square has come into its own over the last couple of years, as we’ve seen some what of a Sartorial renaissance. The pocket square finishes an outfit in ohh so many ways and who would have thought a small piece of silk or cotton could have such an impact on an outfit.

– Anthony McGrath, Online Editor, Clothes Make the Man.

History of Pocket Squares

From Ancient Egypt to Ancient Greece, there are a few conflicting ideas on how far the history of the pocket square really spans, but we do know that what is now solely there for decorative purposes, once held practical value too.

Used mostly, as one would imagine, to wipe your brow or blow your nose, the handkerchief as a practical tool started to gain popularity in Europe during the 1400s. At this point they were mainly made from exotic fabrics such as silk and embroidered with beautiful patterns which would demonstrate great wealth and status.

It was only in the 1900s that the handkerchief finally found its way in to the breast pocket’s of gentlemen, as they didn’t want their pristine cloths mixing with coins and other dirty items in their trouser pocket.

During Hollywood’s Golden Age in the 30s and 40s, movie stars began wearing them in unique ways to portray their own personal style. Fred Astaire of course went for a showy, dynamic fold for his square, whilst Cary Grant preferred his with the tip pointing downwards.


How to Wear a Pocket Square Cheat Sheet

  • Solid colours are the simplest option as you don’t have to worry too much about matching your square to the rest of your outfit.
  • Silk / Linen / Cotton pocket squares work best in summer with Wool / Cashmere options better for the winter months.
  • For Black tie settings, it’s best to go with a simple white pocket square.
  • In smart business scenarios, it’s better to stick with solid colours such as red, black, navy.
  • In a casual setting feel free to be a little more experimental with colours, white linen blazers work particularly well with pastel coloured pocket squares.
  • When wearing a three piece suit you’re in the perfect position to vamp it up a bit with a printed pocket square.


And there we have it! The main thing to remember with wearing a pocket scarf is to own it, be confident and others will notice this. If you’re still a little unsure, start with something understated like a deep navy blue and work your way up with prints and patterns as you feel more comfortable.

Feature image from Pinterest

You may also like

error: Alert: Content selection is disabled!!