The 4 Best Ways to Wear a Pocket Square

Almost six months ago, I wrote How to Choose a Pocket Square, showcasing some of Styleforum’s member’s pochettes and how they used them to accessorize various coat and tie combinations.  Still, much like a child eagerly pores over paint brushes when first handed one, many have little to no clue what to do with them, and so impulsively stuff a blob of fabric into their pocket without regard to proper technique.  Granted, it’s not rocket science, but like all other components of classic men’s clothing, a bit of know-how can make a big difference. 
First, should you wear a pocket square?  Forum member Will, creator and writer of A Suitable Wardrobe, recommends a square for all empty breast pockets.  While that may have been appropriate when coats were worn with only trousers, nowadays sport coats can be seen with jeans and even sneakers.  Should you wear a pocket square in this instance?  Since a pocket square dresses up an outfit, whether or not you choose one depends on the look you’re going for.  Are you sporting sneakers and beat-up jeans with that sport coat?  Then skip the square; it’ll look out of place with the casual kicks, like a top hat with pajamas.  A pocket square in a sport coat with raw denim and loafers or wingtips, however, give off a similar dressier vibe.
How should you wear your square?  As with neckties, simpler is better.  Countless YouTube videos demonstrate a dozen ways to fold and place pocket squares in increasingly-complex methods, most of which are fastidiously abominable.  The following are not only the best ways to wear a pocket square, they are the only ways you need to know.
The Square Fold (AKA the TV Fold, AKA the Presidential Fold)
The most basic fold, often seen in Styleforum’s “Conservative Business Dress” thread.  Anesthetized and inoffensive, this option may be perfect for the rest of your outfit if you are going to a formal event or if you work in a conservative office (think grey worsted suits with black captoes).  However, many people make the mistake of folding the square so that none of the seams show, and are instead left with a perfect, paper crease-like fold at the top of their pocket.
This is a proper way to do it: place the square in your pocket so that the edges of the square are facing the shoulder and arm.  This gives a touch of visual interest to an otherwise, well, boring square.  Try angling the outside corner up and out toward your deltoid.  This way the diagonal lines of the square’s edges echo the same contours of the V of your suit and lapels.  For extra credit, space the edges apart haphazardly as you fold to create a more organic square-ish fold.  This type of fold works well with small repeating patterns, and of course, plain white linen or cotton.
The Three Point Fold
Variations of this one exist (Two and Four Points), but even numbers seem to make an already artificially manipulated piece of frivolous cloth overly contrived.  To do it, simply fold the square in half on the diagonal, bring the left corner up over the top so it falls on the right, and then the right corner behind so it falls on the left.  A less studied look than the Square Fold, and works with all squares.
The Puff
The puff is basically a half circle, accomplished in several ways.  The easiest way is by simply shoving the points down in your pocket, leaving a puff at the top.  This can sometimes look a little shapeless, so another way is by pinching the middle of the square, twisting it, and folding it.  This creates soft pleats that give the square an interesting dimensionality.  Another way similar to the last is after pinching the square, bringing it through an O of your thumb and forefinger, and then folding it in half so that the points are either behind or on the outside edge of the puff.  Best for abstracts, paisleys, and large prints.
The Whatever
Another option is to do combinations of the three above. I find myself doing the Three Point and Puff Fold regularly. I also like how Will at A Suitable Wardrobe puts it: shove it in, direct points toward your left, and forget about it.  This is basically what is demonstrated by TTO here:
Pocket squares, like most articles of menswear, follow simple rules of aesthetics and harmony.  You may not always need one, but when you do, practicing these tried-and-true methods can make your pocket square an elegant accompaniment to your ensemble. Finally, for your edification and viewing enjoyment, I’ve put together a video, which you can watch below:

5 Rules to Dress Like an Italian

Before moving to the US a few years ago, I didn’t really have a clear idea of what Italian style really was. I’ve lived all my life surrounded by people with different tastes in fashion, but I never fully realized the impact of Italian culture in the choice of our  garments.

This is valid for womenswear as much as for menswear; I still get baffled when people stop me to tell me that they like my outfit or they ask my opinion on something in a store. When I go shopping with my husband and I start chatting with employees and customers, many ask me: “How can I dress to look like I’m Italian?”

Usually at that point I puff my chest and put on a big smile, and I start listing all the points that I have observed as key to “Italian Style”. Here they are. Take notes.


This is a golden rule for Italians, in menswear as well as in every aspect of life: abandon stiff constructions and extra thick padded shoulders and embrace softer, looser fabrics that move with your body.

You can read this as a philosophy of life: clothes are our shell, and we want to feel comfortable in them in order to have a positive attitude towards life. Freedom of movement is the first step towards expressing yourself at the fullest. Neapolitan tailoring was born to provide an alternative to stiff English tailoring that didn’t quite suit the Italian spirit (and didn’t allow for nearly enough gesticulation).


It might sound strange, but while it is extremely difficult to dress up casual clothes, it is quite easy to dress down formal ones – and the results can be quite stunning.

In Italy, nobody wants to look too formal. There is a cultural element in this assumption as well: Italians believe that people should not take themselves too seriously, and dressing up in a homogenous way will not make anyone look any more interesting to the society.

This leads me to the next point: yes, it is possible to look elegant without wearing only formal clothes.

How? Easy: you dress down your formal clothes. As long as your clothes fit you well, you can play around with them. That’s why it’s important to invest in casualwear just as much as in formal garments: a few, nice pieces to pair with your more formal clothes will be your best allies in creating a classic (and unique) style that can be worn on any occasion. It’s not a secret that Italians love their turtlenecks – and thank God the trend has been picking up in the menswear community – but there are endless possibilities to dress down your favorite jackets and pants: polo shirts, button-downs, chinos, colorful scarves, etc.

Even easier: wear your best suit and lose the tie. Unbutton the first two buttons of the shirt and vai con Dio.

@AlessandroSquarzi is a master in stepping up his style by playing around with casual and even workwear pieces.


“The purest and most thoughtful minds are those which love colour the most,” wrote John Ruskin in 1853. Of course, he was referring to colors in painting: he was trying to defend Turner’s scandalous skies, which inflamed the walls of the art galleries in London, where cloudy greys and muddy browns were the dominant colors.

Italians are not afraid of colors. In fact, we never were. Think of the vibrant landscapes of the Macchiaioli, who were Ruskin’s contemporaries, and apply that sensibility to menswear.

You’ll see every color of the rainbow walking in any boutique in Italy – whether it is just a little touch, like the stitching, or a vibrant garment that many Americans would label as a “statement” piece.

Combining color is an art – Ruskin knew that well. The wrong hue could throw the balance off and turn poetry into disaster.

Educate your eyes to appreciate colors that go beyond blue and brown, and you’ll experience the same type of sensuous pleasure a painting by Turner provides: harmony, and a tingling of the soul that will be an inspiration for the people around you.


If you see someone wearing Birkenstocks in Italy, you can be certain it is a German or American tourist. There is a sort of social stigma on Birkenstocks (and on other, similar-looking footwear) as Italians simply cannot accept them as real shoes. They might secretly wear them around the house, while gardening, but there is no way an Italian would ever show in up in public wearing a pair of Birkenstocks.

As a general rule, try not to choose comfort over style. Pick your clothes carefully, so that they are both comfortable and stylish, and keep those sweatpants in the gym bag.

If you’re looking for casual and summer footwear, I recommend espadrilles; specifically, I like these by Zabattigli, which are hand-woven in Capri. The rope keeps the soles of your feet aerated and fresh, and the sleek style is way sexier than those bulky, Teutonic, panzer-looking shoes.


In Italy, people dress well because they like to. Period.

This is something that is very eradicated in me, and that people don’t understand in America. My husband still gets confused when I wear makeup and a nice dress to go buy groceries.

“Why do you dress up like that? We’re going to Ralph’s.”

“Because I like it,” I reply every time, as I spray my most expensive cologne extensively on my neck.

There is a crucial distinction between being well-dressed and being overdressed. Obviously, I would look ridiculous wearing a cocktail dress in a grocery store; but a nice dress, why not? The same goes for men: nobody is saying you should wear your top hat to go to the movies, but a nice blazer and a few, carefully picked accessories will make you stand out for your elegance without looking out of place.

To everyone worrying about what people will think of your choice of clothes, I say: if you are the only one well-dressed person in the room, you shouldn’t be the one feeling embarrassed. Rather, all the others should be the ones feeling shabby and looking up to you.

Occasions shouldn’t make the man. We are better than the sum of social boundaries we are submitted to, and clothes are a way to let our personality spark any time of the day, any day of our lives. Why waste an opportunity to do so, and let trivial actions get in the way?

You might have figured at this point that the Italian Style is much more about attitude than it is about clothes. I’ve read many articles on the Internet that teach you how to “dress like an Italian,” and I think they all missed the point.

There are really no rules when it comes to expressing yourself, and even an extravagant flair can be turned into a jaw-dropping detail that will step up your game. This is the secret of the Italian Style: as long as you like what you wear, and you’re confident enough to pull it off, you’ll be fine.


How to Pair Fabric Textures: Choosing a Suit Fabric, Pt. 2

Wool plain weave or twill suit, cotton oxford or broadcloth shirt, silk tie.

That’s the current, standard armor of menswear that man begins with, is married in, and is eventually buried in – it’s a relatively easy recipe to remember, and it works very well.  Make sure everything fits, choose colors that go well together, and you’re done.  Easy peasy. Last time, we talked about the basics of how to choose a suit fabric, but there are other options – and you’ll have to consider how to pair fabric textures.

Besides twill, there’s mohair sharkskin for Mods, slick gabardine for Rockers, and cavalry twill for hunters.  There’s fresco for the heat, flannel for the cold, and tweed for a pint in the pub. And that’s just the plain stuff – patterns abound, suitable for whatever environment you find yourself in.  Try birdseye for the boardroom, chalkstripes for less formal offices, and windowpanes, glen checks, and gunclubs for the casual or adventurous.  Some men see a soft cashmere tie and cannot resist its fuzzy allure.  Others succumb to the easy-going appeal of a rumply linen suit.  All well and good, but understand that arbitrarily changing one ingredient in the recipe can lead to an unsavory sight.  The heft, feel, and texture of fabric thus come into play when choosing one for a suit.

The importance of texture in clothing is often overlooked and under-appreciated.  Those ignorant of it can make an otherwise winning ensemble fail, whereas those who understand how textures play together can upgrade even mediocre outfits with depth and interest.

First, it should be noted that the most basic iteration of menswear – dark wool suit in a plain weave, light broadcloth cotton shirt, silk twill or grenadine tie – is in and of itself a wonderful mixture of textures.  As the main component, a suit in a modest wool is discreet, elegant, and light-absorbing.  The cotton shirt adds another layer of texture, tightly woven and offering a hint of sheen.  Finally, the silk fabric of a fine tie gives off a soft luster that delicately reflects light.   Let’s go over some basic combinations below:

These three elements – again, wool suit, cotton shirt, silk tie – when worn in classic woven fabrics such as the examples above, are your bread and butter.  But…

What if you toast your bread, and melt your butter?  You have now introduced two new textures that are miles beyond their original state: the once spongy bread is now crispy and crunchy on the outside, soft and chewy on the inside; and the formerly waxy pat of butter now oozes like smooth, liquid velvet through its crevices.  

Here’s a couple of simple tables that can help pull together your outfit so that your fixins fit in:

choosing a suit fabric styleforum alternative suit fabrics suit fabric pairings how to pair fabric textures 

Deviating from the tried-and-true triad of menswear can seem a bit complicated, but hopefully the above charts will assist in making it less so.  Bear in mind they are neither exhaustive nor unyielding, but meant to be used as a guide to assist in making sure your ensemble “ingredients” form a pleasant picture.  

At the top of each chart, there is the wool suit in a plain weave, silk twill or grenadine tie, and broadcloth shirt, which you already are familiar with.  As you go down the chart, the fabrics get more casual. Here are some examples of how to pair fabric textures:

Warm Weather

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And here are some good examples of how to pair fabric textures for cool weather

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A few items are always seasonally correct and good for most outfits:

Silk ties; twill, or – slightly more casual – knit

Silk pocket squares

White pocket squares in cotton or linen

Other factors, such as patterns, also play a role in the formality of menswear.  That’s already been discussed in another article, but hopefully these charts and pictures will help when putting together items based on texture.  When all ingredients come together as a whole, the end result – simple or intricate, urbane or nonchalant – will be a palatable portrait of classic menswear in coat and tie.

7 Ways to Wear Boots With Jeans

No, it’s not rocket science, and yes, the key is to put the jeans on before your boots, but there’s still more than one way to wear boots with your jeans.

1. The Stack

ways to wear boots with jeans

Jeans, APC; Boots, Scarosso

Simple: do nothing. Put your boots on, pull your jeans over the shaft, let ’em stack up on top of the boots. Ideally, you don’t want wrinkles running all the way up your legs; instead, leave an extra couple of inches to your inseam and you’ll end up with nice honeycomb fades

Works best with: slim denim

2. The Micro-Cuff

Also simple – you know what, they’re all simple. In this case, you turn up the hem of your jeans – but not by much, just enough to leave a sliver of well-worn selvage denim showing. Vary this by accompanying it with a stack, or with a jean hemmed to a shorter length to show off the shaft of your boot.

Works best with: slim-straight jeans

3. The Regular Cuff

ways to wear boots with jeans

Jeans, Uniqlo; Boots, Nonnative

Cuff your jeans once. Done.

Works best with: slim, slim-straight jeans

4. The Double Cuff

ways to wear boots with jeans

Jeans, Uniqlo; Boots, Nonnative

For a thicker cuff, turn your hem over twice and your jeans should sit just at your ankle. This is an easy option that will look nice with most boots.

Works best with: slim-straight or straight jeans

5. The Triple Cuff

ways to wear boots with jeans

Jeans, Shockoe Atelier; Boots, Nonnative

Not too hard – roll it up one more time. It’ll give you a thicker cuff, and although this looks good with heavy boots, I also like it with sleeker silhouette and taller shaft.

Works best with: a straighter-legged pair of denim so that the bigger cuff doesn’t overwhelm the leg of the jeans.

6. The Narrow Roll

ways to wear boots with jeans

Jeans, Evan Kinori; Boots, Peter Nappi

Make like you’re rolling a single micro-cuff, and then keep going as high as you like. Wear the hem low to stack on top of your boots, or pull it high for a cool silhouette.

Works best with: straight or relaxed denim.

7. The Railroader

ways to wear boots with jeans

Jean, Kapital; Boots, Guidi & Rossellini

Only for the dedicated: instead of making small cuffs, turn your hem inside out and pull the cuff halfway up your shin. This has the potential to be massively rad or not rad at all – you need to back it up with an outfit that meshes well.

Works best with: stiff, straight-leg jeans and heavy boots (like engineer, combat, or service boots).

How to Choose a Pocket Square

Are you a pro-pocket square person? Perhaps you’ve heard that they are the cheapest way to “upgrade” your wardrobe, but you’re hesitant. You feel safe in your white shirt, navy suit, and black shoes, and while you’ve seen them on other guys, and even liked one or two, you could never see yourself wearing one. Maybe it’s because you don’t want to call attention to yourself. You’re wary of getting into uncertain territory, and after all, a pocket square serves no real practical purpose.

On the other hand, you may have completely lost your mind and gone square crazy, spending as much on them as you would for a well-made suit. You’ve bought untold folds of squares in every color of the rainbow. You even have a division of solids, designs and patterns, cottons and linens, woolen and silk. And why not? Most are dirt cheap, even if you splurge on one, you won’t be dropping much more than a Benjamin.

Let’s assume for a moment that you are a balanced individual that enjoys classic menswear and wishes to appear like someone who cares, but not fastidiously so. You’ve seen pictures of old Hollywood stars or various gentlemen throughout the past 100 years and admired how some of them can pull off the pochette. You’ve considered getting one; you may even have a few. How do you wear it without looking like you’ve consulted an article – like this one?
Many how-to’s have been written; often peppered with precision diagrams, architectural blueprints, and earnest cries to wear a pocket square in order to defend the dapper man’s heritage. This is not one of those articles. In fact, it should be said that it is better to wear no pocket square at all than to wear an ill-chosen one, and let’s face it: most pocket squares are hideous. Rather, we’ll showcase some of how some of Styleforum’s own members wear them, and learn from their example.

Our first member to showcase is @Pliny. I’ve always liked how his outfits combine differing scales of pattern, even though I maintain he takes horrible pictures of his successes. Let’s look at a few examples.

When wearing a small-scale gunclub jacket, a pocket square with a large design keeps things from looking too busy. Notice how the mostly cream color of the two complement the jacket, shirt, and tie in both ensembles. These are perfect examples of how well these types of pocket squares work with practically any combination of coat and tie, including, as Pliny demonstrates above, a solid grey suit.


Next up we have @TTO, of whom I wish the forum saw more. His creative nod to vintage style may not be to everyone’s taste, but it is always refreshing.

One of the regular pitfalls of the pocket square is wearing one that doesn’t contrast enough with the jacket you’ve chosen. TTO wisely opts for bold white stripes to set his square apart and still echo the light shade of his blue shirt.

Finally, we have Mr. Six, who always has a small sliver of good taste stuffed into his breast pocket. Although not always in solid suits, these two pictures showcase how even in a conservative environment one can enjoy pocket squares without resorting to absurd designs or obnoxious colors.



In both pictures, Mr.Six has chosen a square that contrasts with his jacket, either lighter or darker. Far from standing out, the luminance of the pocket square in the first photo harmonizes well with the shirt, and the dark colors of the pocket square in the second echo his tie.

Pocket squares, more than most other items in a man’s wardrobe, are difficult to wear well. The ideal pocket square choice neither adds nor takes away from an ensemble, and is instead a harmonious but not attention-grabbing element of the outfit. Far from being detrimental, such choices are in fact a good thing. The components of an outfit should look as though the wearer carelessly threw them together in such a way that nothing matches but everything complements; neither too studied nor too heterogenous. Admittedly, this is more of an art than science, but there are a few guidelines that can help you chose a pocket square that at the very least jives with the rest of your outfit, if not a slam dunk:

  • Silk is always a correct choice, but shun overly shiny squares. You don’t want iridescence to blind onlookers and take their eyes away from your gleaming smile.
  • Solid-colored silk squares are bad, except perhaps in cream. White linen or cotton is far better, and is by far the most versatile pocket square you can own. Really, if a plain white linen or cotton pocket square won’t work, you’re better off with no square at all.
  • Try to contrast the square with the color and brightness of your jacket, as well as with the scale of the patterns in your outfit.
  • Avoid pocket squares with the same pattern as your tie to keep from looking too calculated.
  • Don’t succumb to the interweb’s love of the pocket square explosion. That’s just a stylist’s way of quickly stuffing the fabric into a mannequin’s breast pocket. Keep the puff politely subdued and prevent your points from peacocking.

These above pictures are just a handful of the many good examples of pocket squares you can find on the forum. There’s an entire thread devoted to them, and many users are happy to go into even further depth, including seasonality and fabric choice. The perfect pochette can subtly enliven and enrich your ensemble, but choose unwisely and you may look overly affected and foppish.

Really, at the end of the day, it’s just a useless piece of fabric, and if no one noticed your square, you have claimed a victory.