Men’s Fashion Advice: Pocket Squares

Fred Astaire Pocket Square If you’re wearing a jacket (and you should) that has a breast pocket, that pocket should be filled to overflowing with a pocket “square”. The material of this object must only be cotton, linen, or silk. Polyester or any blend is forbidden because it looks cheesy.

Why wear one? Several reasons. The pocket square, like the tie, breaks up the monotony caused by draping one’s chest entirely in one fabric. Nobody now has the fortitude to wear a boutonniere, but these provide the same effect. The more the jacket angles towards one color and lack of pattern, the more the pocket square is needed. And if a jacket is loudly patterned, again, the pocket square can bring relief to the eye.

Ancient advice recommends a pocket square not be cut from the same bot as the tie. This advice is ancient because it is true. If the tie and pocket square match, the eye is strongly drawn to them, and you risk looking studied or goofy: worse, nobody will look at your face. Matching a pocket square to tie can be done, but the probability of a pleasing result is so low that it should not be attempted by the amateur.

Sean Connery Pocket Square There are four elements to wearing a pocket square: pattern, color, material, and folding. The pattern should usually be unlike the jacket entirely, especially if the color of the square is similar to the jacket. The more the colors of the jacket and pocket square are different, the more the patterns on both can match. If your jacket is loud, a simple white pocket square is best. But again, if you’re wearing a sharp, formal suit or dinner jacket, white is best. Pocket square patterns can be reminiscent of the tie, but should never match it. But neither should the pattern contrast too abruptly with the tie: don’t mix stripes and polka dots, for instance.

Simple colors are preferred. Shocking or bright hues draw the eye to them. Remember: the goal of a pocket square is similar to the visible half inch or less of shirt linen that peeps out the bottom of jacket sleeves. They both provide framing and relief. If your shirt linen stuck out several inches (or your jacket sleeves are cut too short), that is all people will see. One reason to dress well is to advertise yourself, not your clothes.

Humphrey Bogart Pocket SquareThere are some obvious, but not strict, rules about material. If you should end up in a tuxedo, a white silk pocket square is the only real option. As with all clothes, the texture of the pocket square should angle toward the texture of the jacket. Sports jackets call out for cotton or linen. Wool wants silk.

Pocket squares are not cheap, and many men won’t buy them thinking that the cost of a piece of material whose only purpose is decorative is not worth the cost. Naturally, this forgets that occasionally a pocket square can be lent to a lady. As for cost, stick to simple white linen: it almost always works. Plus, you can make your own. For the past few years, cheap silk scarves from India and Pakistan have been sold in the States for as little as $5. I have taken these and cut pocket squares from them (one scarf will make a dozen). Similarly, old ties found in thrift shops can be pressed into service; but don’t use “rep” ties.



William Faulkner Pocket SquareThe more formal your dress, the less conspicuous your pocket square should be. If you’re testifying in front of Congress wearing a dark blue or black suit, the pocket square (preferably white) must be folded into a square, and no more than half an inch should peek out above the pocket. If you’re suit is still on the formal side, but not too severe, the method of folding so that the four tips of the linen show. When Fox television’s Brett Baier first took to wearing pocket squares, he would use this fold, but the tips stuck out so severely that you had the idea that if you touched one, you would cut yourself. The severity was all that was seen.

The younger you are, the less of your pocket square should show. If you’re in your twenties, you haven’t yet earned the right to be cavalier. Conversely, the older you, the freer you can be with showing silk. Once you’re past sixty, the pocket square can practically erupt from its home. This adds character. Of course, part of the reason this works is because when you’re older, your clothes are, too, and people expect a certain rumpled appearance.


  1. DAV

    I wonder where the cigar ash is supposed to be eventually placed by the reclining Sean (?). Isn’t that what the breast pocket is really for?

  2. Rich

    It would be nice if you would point to a reliable place for the folding methods. The 4 corner one sounds interesting

  3. Tim Reed

    Real men don’t worry so much about fashion.
    No doubt the men in these photos had their wear chosen by some studio employee or their wife or girlfriend.

  4. Ray

    This is a fun article. It makes me glad that I am still in my pajamas.

  5. RR Ryan

    Tim- Or boyfriend. Let’s face it: these guys are all good looking and pulled together in a guy sort of way.

  6. max


    cigar ash, if it needs a home in your clothing (which it shouldn’t in a perfect world, and if you find a perfect world please let me know where so I can move there), goes into the trouser cuff.

    As for good looking men, ah you are missing the power of a well cut suit to improve the appearance of any man. A suit emphasizes the shoulders and chest while minimizing the waist producing the inverted triangle even on bodies which are more like a circle (erg Dom Delouise). The “modern” suit reached the perfection of making men of all body types look good over a century ago and since then only minor modifications have been made. And one of the great joys of a suit is that men can in fact chose their own suits successfully without being fashion conscious, indeed being fashion conscious might steer the unwitting into a faux pas like the zoot suit.

  7. ed

    Of course, in order to avail myself of this wonderful advice, I would need to go out and purchase some pocket squares. Oh, and some suits. The moths got my last one several years back.

    Just an aside. It used to frequent a cleaners who would insert a faux pocket square in all my newly cleaned suits. Just a little hint of fabric anchored to a business card (their’s , of course). Clever.

  8. Katie

    Ray, you can still look snazzy in your pajamas. In the old-time movies, men in bathrobes sometimes have some fabric flooding from their breast pocket (are bathrobes still constructed in this way?). In a pinch you could use a washcloth so you look presentable to room service.

  9. Thank you, Master, for your timely and enlightening instructions. I earlier blushed with naive shame because at first I had failed to “pocket square” my bathrobe, but now have completed that wardrobe “look” with a suitable item. In this case a spare Huggie – tiny granddaughter is expected to visit soon.

    Do you have any advice as to the location of pocket squares on bib overalls? Mine have three sectioned upper pockets. Up to now I’ve been using the right hip pocket but I see now that presents the wrong impression.

  10. Briggs


    As a matter of fact, I do. A red hankie is just the thing for the bib pocket. It should be off center and not at all neat.


    Fred Astaire did, too, as you know.


    There is an inverse correlation between a post’s popularity measured in terms of hits and its number of comments. This post has already seen about 3,000 hits of this writing, and not slowing down. Yet it only has a handful of comments.

    Tim Reed,

    Not so. Astaire was, of course, well know for caring about his appearance. But so was Humphrey Bogart. He took great pains to look good in a double-breasted, something men of his stature have great difficulty with. You might have a point about Connery, but I don’t think anybody would accuse Falkner of having had somebody dress him.


    Cigar ash belongs just anywhere. Never worry about where it falls.


    Best method for everyday wear is to grab the thing, almost blindly, in the middle. Then, without looking, cram it into the breast pocket, the corners disappearing inside. For formal wear, any simple, sharp simple fold will do.

  11. Tom Frank

    Wonderful article!

    I anxiously await the follow-up on the proper presentation of a pocket watch.

    There is the traditional vest pocket, or the more bohemian jacket pocket. Albert chain or single ended? Silver or gold chain? Must it match the watch case material? How about a fob (yes or no)?

  12. Briggs


    I just discovered (7 pm, EST), that today’s Wall Street Journal has a filler graphic on folding a pocket square. Page D4.

  13. Gary P

    Thanks for the article. It reminded me to put a nice crisp red bandana in the pocket of my new black Carhartt vest. I doesn’t stick out of the deep pocket but the vest already has a tasteful white Carhartt label on the front that works well with the brass zipper to break up the solid color of the vest. It goes well with any long sleeve shirt, from your your fancy white polyester to a basic green or red flannel.

    Don’t forget the shoelaces in your boots. Assuming black boots, a subdued multicolored lace will go well if you need to add color to your ensemble. I like a mixed brown and black bootlace when I wear the black vest with black jeans.

    Remember, never use a gold or silver chain with your wallet. Only stainless steel has the dull sheen than keeps it from looking gaudy. (Plus why would you use a chain that is more valuable than what is in your wallet?)

  14. If I cna get back down a couple of belt sizes, this is the perfect advice article. I love wearing a suit to work!

  15. “If you’re suit is still on the formal side, but not too severe, the method of folding so that the four tips of the linen show.”

    You’re, not your. Not being a jerk, just something anyone might miss fixing!

  16. wolf t.

    I usually stick a condom into my breast pocket. It comes in a square pack and I let half an inch stick out. When I want to impress the ladies I usually unroll a Magnum and let it hang down the front of my jacket.

  17. AusieDan

    Thank you WMB.
    I really enjoyed that.
    I usually come to your site for education about statistical matters.
    But, being quite old, I tend to let standards slip.
    This has made me sit up and take notice
    and realise that AGW is not such a threat after all.
    Well done.

  18. Wonderful explanation of the pocket square, although the picture of Fred at the top almost makes the text superfluous. I’m sold.

  19. GoneWithTheWind

    I generally wear jeans and a colored pocket tee shirt. What color pocket square should I wear to make me look like 007? Seriously who cares what you wear? I wore suits when I worked and when I retired I gave them all to goodwill. I hope to never wear a tie again. my idea of dressing up is wearing freshly washed jeans with one of my untorn tee shirts. But I generally reserve that for weddings and funerals.

  20. Capt. Craig

    What a pile of crap and it is amazing the number of metros who have commented. At the risk of giving ammunition to the truly unworthy, I always stuffed a pair of silk panties in my breast pocket and they were of course color co-ordinated with my tie.
    Over the years there arose those situations that allowed me to nonchalantly remove the panties and wipe my brow then return the silk to my pocket and carry on with aplomb thus gathering status and usually a happy ending to the evening and the envy of the lesser enabled wannabee studs.

  21. Rod

    I’m giving a presentation at the end of this week and I need a figure for the probability that a matching tie and pocket square will be pleasing. Any help will probably be appreciated.

  22. Rod

    A couple of things about Capt. Craig’s post. Can a pair of panties be a pocket square? Secondly I’m thinking that you must be an airline pilot and that all apparel worn by staff can be described as colour co-ordinated.

  23. Men’s formal wear have change alot over the years. I think personally mens formal wear back in the day was more fashionable then formals today. Everything for the men has to have a street twist to it making it less formal less interesting.

    Womens Clothing

  24. Speed Doesn't Kill, It Bores

    Unlike search engines, Speed, tedious sarcasm has been around forever. Perhaps Rich just wanted a recommendation from someone who’s written on the subject. Why don’t you adjust your meds… or just do us all a favor and break your keyboard.

  25. max


    perhaps over the centuries but not over the years. A man can wear a suit made 100 years ago, and unless it was one of those attempts at fashion, and not look at all out of place – heck a man can walk into Brooks Brothers today and buy a new Brooks Brothers Suit (TM?) which is the same suit their ancestor bought over a century ago at Brooks Brothers and not look at all out of place.

    That doesn’t mean designers haven’t tried hard to change men’s “formal” wear, just without success (“formal” is in quotes because a suit by itself isn’t “formal” wear, it is business wear). The fact that a man can buy suits in his 20s and wear them for the rest of his life without going out of style isn’t good for fashion designers who want to sell that man a new wardrobe every year, but since the suit is perfect they are stymied. Most fashion designers have given up on trying to change the suit and only play around the edges with the accessories; ties, shirt collars & such which are all nice but since the suit itself is perfect don’t have a strong impact.

    As for actual formal wear, while some men still wear the undercoat most have chosen to use a vest or even a cummerbund in their formal wear. This isn’t actually a new fashion, merely a re-purposing of more casual wear for formal occasions. A man these days can even get away with wearing a tuxedo to a wedding for instance whereas 150 years ago a tuxedo was was what a gentleman wore out for a night on the town.

  26. gcb

    I rather enjoy these “fashion” (for want of a less metrosexual term) articles – over the past year it’s been my goal to “raise the bar” in my office in terms of attire, and I’ve received some helpful advice here from Mr. Briggs. Now, while my compatriots go around in shirt sleeves, I’m rarely found without a vest and sport coat (I’ve accumulated an impressive selection of Harris Tweeds), and a fedora adorns my head on the way to and from the office. There are still some refinements to make, but I know that, should I be called before the president of the financial institution I work for to explain the most recent reports, I will stand out from the herd. Of course it’s an affectation to some extent, but then again, much of what we do is just that. Mine is just more obvious.

Leave a Reply

Your email address will not be published. Required fields are marked *