As we have seen in the good taste thread, SquareFail is the most common reason an outfit sux. Everything else can be good and the square alone can bring down the whole. SquareFail has three causes: 1) A bad square. 2) A good square badly chosen. 3) A good square well chosen but improperly folded and placed. Before we take each in turn, a macro comment. In this day and age, wearing a square at all is a statement. It is dandified, it stands out, it says you are a "dresser" because squares have become incredibly uncommon. I have noticed something of a square revival in Manhattan over the last couple of years; I don't know what it's like in other cities. But even in the NYC square revival, you will still see them on less than 50% of men and probably less than 25%. This is why it is so important to avoid SquareFail. You're already taking a risk. You need to make sure you get it right. Cause #1: Bad squares are legion. Good squares are few. It is essential that your square be tasteful. That doesn't mean dull. A lively square can work, depending on what it's worn with (topic #2) and how it is worn (#3). But it is best to start from the simplest, quietest and easiest to pair. The ne plus utlra square is plain white linen. You need some of these. If you have these and no others, you will be fine. You will hear voices here who oppose this square, or support it only in limited circumstances (e.g., never with a white shirt). Do not allow yourself to be beguiled by these false sirens. Their winds will carry your hull to the shoals. White linen goes with everything. Other linen: I am not inalterably opposed. But these need to be approached with caution. Linen squares with printed figures on them are automatic fail. The most common you will see are linen with a colored border. These MUST be hand-rolled to have any hope of not looking like hell. While I am no longer crazy about these, they are not bad. Any other pattern has to be plaid of some sort; these we can judge case by case, it's hard to give guidelines. Cotton: There are two good types of cotton squares, the S&G ones, and the Drake's Moghul prints. Both are for summer. The S&G cottons are the only jacquard items that should ever be in your wardrobe. Ever. These should have a hand rolled edge, but unlike white linen, not a doubled up border. Wool/cashmere or blends: these can be nice, especially the Drake hunter prints. I tend to avoid solids. Needless to say, these are for winter. Silk: should be your mainstay after white linen. But, as we have seen, they are very hard to get right. They should of course always have a hand-rolled edge and they should NEVER be woven. There is unfortunately an "I know it when I see it" quality to taste here but we shall do our best. Here are some things to keep in mind: -If it looks like a tie move on. Silk squares should look decidedly different from ties. Very large motifs that would be completely awful on ties work well here, especially not repeating motifs like certain Persian rugs. Because the motif will be out of scale with those of your ties, you are at much less risk of looking matchy. Big print squares give you opportunities. You have the option of which particular colors in the square you want to show, which makes them more versatile. Be especially careful of repeating motifs, which is not to say avoid. What you don’t want are small repeating figures. A coin-sized motif is about as small as you want to go. Small dots are a tie pattern that we see way too much on squares. Avoid. -It should have a border. Borderless squares look incomplete, like they were cut out of a piece of cloth at random. -Treat geometric patterns with caution. Again, you don’t want it to look like a tie. You also don’t want the pattern to make the square look like woven silk. -Be careful with the finish. As a general matter, “wet” or shiny textures are less flattering on men that dry ones. A silk square is the one place that some wet is good but don’t overdo it. No reflective satins. -Solid silk is OK but only in VERY dark or VERY dull colors, nothing bright. Nay will be aghast but very dark, dull burg or green make nice squares. Cream is OK too. If it looks like Donald Trump would wear it, you shouldn’t. Cause #2 By the far the most common error in this category is to be too matchy. Green tie + green square. Or, blue shirt + pale blue S&G cotton square. Just don’t ever do this. Guaranteed SquareFail. At most you want to pick up a hint of color in the tie or shirt with the square. At most. And by this I do not mean, you have a shirt with a sky blue stripe so you choose a solid sky blue square. No. I mean, a square with a splash of blue in it is fine if there is more going on. The more distinct the color you are picking up, the worse it looks if the square matches that totally. For instance, a tie with a nice rust-orange motif will look like shit with a solid orange square. Actually, a solid orange square will always look like shit. But really the square does not have to pick up anything. It can be totally unrelated as long as its colors are complementary. This is not the time or place for color theory but hopefully you all by now have a sense for what unrelated colors go together. Watch what foo does, his square never matches anything and rarely picks anything up. It’s typically unrelated but complementary. You also have to watch against matchiness with the pattern. Really, this is the baseline reason to avoid squares with small repeating patterns. The vast majority of ties are like that. Beyond the fact that you don’t want your square to look like a tie, you don’t want it’s patter to be the same scale of or otherwise look similar to the tie. Don’t pick a square that gets lost against the suit. I have a square I like a great deal that has a lot of navy in it. I never wear it with a navy suit because it gets lost. What the eye sees is some bizarre cottage cheese wrinkle in the chest. The square needs to contrast with the suit cloth. Your livelier, more boisterous squares should be reserved for otherwise sedate outfits. If you have a lot going on elsewhere, choose a simple square. Remember, white linen is auto-nonfail. When in doubt, just wear that. With a sedate outfit, the square alone can make all the difference. A dark suit, solid blue shirt, and very discreet tie with a white square is correct and fine, but throw in a maroon paisley and the whole is elevated. Textures: try to contrast the texture of the square with the texture of the tie. This is not always necessary but it is a nice touch. Since most ties are silk, this is one reason why white linen is so useful. When you wear wool/cashmere ties in winter (and you should), a silk square is the ideal partner. Cotton squares in summer work with silk ties. Linen summer ties take nicely to silk squares. But of course silk ties go fine with silk squares too, which is why contrasting textures is “nice to do” not “must do.” Cause #3 Fundamental principle: show only a little of your square. No matter what type it is. You are not a clown doing a hanky trick. Just let it peek out to shows some color and break the monotony of the chest. White linen should be laundered, pressed, and TV folded. Not the TV fold where one point is up and you fold it down like closing an envelope. No, that is cheesy. The edges should be exposed. Very simple. The four point fold looks studied and ridiculous. All printed squares, whether silk, cotton, wool or cashmere should be puffed. Silk and wool should always be puffed. See foo to learn how. Cotton S&G takes the Flusser fold. This is hard to explain but the net effect is that all the points are together and they angle slightly up toward the shoulder. Whatever fold you are using, if the square is higher (that is, showing more) on the side of the pocket near the chest, you’ve done it wrong.