Pocket Squares (Part I)

Pocket Squares (Part I)


Handkerchief: Brooks Brothers. Blazer: Lilly Pulitzer.

One of my many issues with the way most men dress is the void of color dressing their breast pocket.  It seems that most men in their 20’s are averse to sport a pocket square or handkerchief.  It is regarded as too pretentious, unneccessary or old man-esque.  This is saddening, as there are few things that can bring an ensemble together as well as a pocket square.  The primary purpose of a pocket square is aesthetic.  A well matched pocket square will tie to the wearers tie or shirt.  There should be some sort of dialogue of color between the items.   Pocket squares look best when they look like they were thought of at the last minute, a sort of impromptu afterthought to an outfit.  However, never, ever, ever should the square be of the same pattern as the tie, ever.  It will look too put together and thought out, it will also draw attention away from the wearers face.

It is best to start with a plain white handkerchief and then move to more complex combinations.  White will go with almost anything and will look best when matched with shirts that have white as the base color and ties that have white in them.  The best squares will be made of Irish linen or silk and have hand rolled and stitched, not machine stitched, edges.

There are many ways to place a pocket square in one’s pocket.  The easiest is to pinch the square in the middle, lift it up, fold it roughly in half which leaving only the 4 corners exposed and then place in the pocket (The final product is shown above, more square is left showing than recommended.  This was done for purposes of example).  It is also recommended that the peaks create a slanting line that follows that of the pocket (also as seen above), this will help maintain the diagonal line, not a horizontal line, across the body.  Utilizing a pocket square is one of the easiest and most effective ways to elevate the appearance of any man in a jacket or suit.  It’s not pretentious, it’s elegant.




  1. Pocket squares set one apart. To my mind, it is virtually impossible to present as the well rounded gentleman without one. To make the attempt is to suggest not only a lack of personal confidence, but to demonstrate a lack of aesthetic. They are de rigueur if one desires to make a favorable impression. Empty coat pockets are nothing short of a billboard advertising that one doesn’t often dress and when one does, one doesn’t really know what one is about. With well-considered combinations of pocket squares, shirts, and shoes a man can convert a single well-made suit into a multiplicity of distinctly different outfits.

  2. Totally disagree. Pocket squares really are pretentious. If you need a little white linen in your pocket to signal confidence, personal security, and identity, then you need to work on your mental health (the biggest determining factor of your confidence), NOT your wardrobe.

    Pocket squares just say “I host soirees, and INSIST on being the center of attention. Watch, as I tell a [uncompelling] story in dramatic fashion, while the crowd looks on in [feigned] amazement!”

    Yeah. Many of these fashion/style/etc. rules are really so arbitrary as to be fairly laughable.

    • Just to warn you, you come across as somewhat egocentric yourself. It is also surprising that someone with such disdain for fashion is on this site in the first place…

    • Mauv,
      Your “opinion” on your own fashion is just that, your own. But be warned, it would be you who would look as lacking in style, professionalism, and the ability to complete your wardrobe if you showed up at most any business meeting lacking a pocket square.

      The idea of it looking pretentious ends with you and clients at the local java house.

  3. I mostly dress with sport coats rather than suits. Are pocket squares appropriate with, say, coarse herringbone? Or should it be reserved for suits?

    • WhollyRoamin,
      Great question. I am of the opinion that a pocket square is as appropriate and essential with a sport coat (like a coarse herringbone) as it is with a suit. I just think that extra attention needs to be paid when making sure the square doesn’t make things too busy paired with a patterned jacket.

  4. Pocket squares are for sissies, fags, effeminate men and all-around losers. They serve no functional purpose and therefore are solely the realm for dandies. Avoid like the plague.

    • Sweet bro, let’s all take our cues from fly-over country mouthbreathers like you who adopted their style from third tier frat date functions.

  5. I totally agree with using a pocket square, though initially the pocket squares purpose was functional. Initially was used for a ‘quick sneeze,’ but not to be ‘put back’ after such usage. Then it seemed to become a compartment for carrying eye glasses . I personally use said pocket for pocket squares, but interested in your thoughts on occasionally placing ones glasses there, regular and/or sunglasses.

  6. 1. Pocket squares do serve a functional purpose – namely, they may be offered to a lady in distress. The failure to grasp this fact, or the disregard for it, is the mark of the petite-bourgeoisie — one reason why the naked suit is so looked down upon.

    2. To Mr Walsh: I would strongly counsel you against using your breast pocket for anything but a pocket square, mainly because I would strongly caution you against ever having a breast pocket without a square in it. At my college there was a teacher who always wore a sportcoat with the breast pocket full of pens; do not be that guy.

  7. Thoughts on plain squares vs those with a border?

    If I’m trying keep it simple and classic, and searching for linen/silk, hand rolled and stitched. But do you have any thoughts on squares that are all one color vs (for example) white with a colored border?

  8. What goes better with suspenders, a neck tie or a bow tie? Also, are white suspenders and tie with a cobalt blue dress shirt a good combination?