Office Hours: No Room For Squares

Lyndon Baines Johnson was not known for his fashion sense, but when the White House invited him to meet with President Truman, the Congressman prepared for the occasion like a dandy. “The first thing he did,” an aide remembered, “was to go out and get his hair cut and his nails manicured.” Next Johnson bought a new pair of shoes and several shirts and ties, to see which combination worked best. Finally, and most agonizingly, he prepared his pocket handkerchief. Johnson called in a particularly well-dressed aide for assistance and “spent part of that evening at his desk” “cursing when it didn’t come out right.”

Even otherwise confident men tend to fuss over pocket handkerchiefs, partly because the accessory remains one of the very few purely decorative items that they wear. An expensive watch has the excuse that it keeps time. A colorful pair of socks also makes shoes feel more comfortable. A handkerchief simply adorns its wearer. For this reason, it attracts attention, if not ridicule.

The 2010 sequel to the 1987 hit movie, “Wall Street,” “Wall Street: Money Never Sleeps” opens with Gordon Gekko, the disgraced corporate raider, being processed for his release from prison. A stone-faced guard gruffly names each personal item taken from Gekko when he entered prison eight years before. The first item doubles as the first words of the movie, “One silk pocket square.” Gekko’s face is not shown in the scene nor is he named. Instead, the “silk pocket square” announces Gekko’s identity. 

Alan Flusser, who famously consulted on the wardrobe for the original “Wall Street” movie, observed that a breast pocket without a pocket square “looks naked.” The five Wall Street analysts the New York Times interviewed about the sequel offered a different opinion:

New York Times interviewer: What about the fashion? Do young financiers really dress that well?

Goldman analyst: No one wears pocket squares.

Credit Suisse analyst: Yeah, he’d be ridiculed.

The style of “Wall Street” draws from cinematic history more than actual Wall Street fashion. Combined with the power suits and the colorful braces that Gekko favors, the silk pocket square casts him as a debonair, white-collar version of Hollywood’s traditional mobster, the “squat gangster in his derby and three-piece suit with boutonniere and pointed pocket handkerchief” (as the writer Robert Coover described him). No matter how often Gekko proclaims he is a changed man, the handkerchief insists on his enduring criminality.

Discussions of pocket handkerchief tend to emphasize its perceived associations, whether appealing or not. Attorney Chris Zampogna, a former president of the Washington DC Bar Association, advises clients to avoid wearing a pocket square in court because they call to mind figures like Gordon Gekko, “You don’t want to wear the pocket square and look like a New York City, Wall Street, over-the-top guy.” Roger Stone argues the opposite, “The pocket square, properly contrived, finishes a man’s look. With good tailoring and well-chosen neckwear, the look connotes power, taste, refinement, manners. The naked pocket connotes the opposite: working class, tasteless, base, crude, ignorant.”

Stone’s comments represent one of the least attractive aspects of discussions of traditional men’s clothing: the tendency to assign dubious class distinctions to particular items in order to disparage those considered déclassé. Note, for instance, how Stone describes “working class” as synonymous with “tasteless, base, crude, ignorant.” 

Like several other innovations in modern men’s wear, the pocket square was popularized by the Duke of Windsor. “The haberdashers have learned from long experience that follow the Prince in his fashions is money in the pockets, hence they are selling the new handkerchiefs by the dozen to young bloods,” the New York Times breathlessly reported in 1924. The Duke of Windsor was a dazzling dresser and an otherwise unpleasant human being. His example shows that sartorial style should be admired for what it is, for the skill and flair it demonstrates and the pleasures it gives, and not for what it is not, as a marker of objectionable values.  

Of course, there are several kinds of pocket handkerchiefs, distinguished by material and pattern. I find the so-called TV fold—a white linen handkerchief arranged in a straight line across the pocket—a little too severe. I prefer pocket handkerchiefs when they add a splash of color or texture to an otherwise restrained outfit. I am particular to handkerchiefs whose patterns—of maps or bridges, for instance—are indiscernible when they are puffed in a pocket. They present a playful little mystery and suggest, at least to me, that clothes might be best enjoyed for the pure fun they bring into our lives. — DAVID CAPLAN

David Caplan is Charles M. Weis Professor of English at Ohio Wesleyan University.

Pocket square from R. Hanauer. 

16 Comments on "Office Hours: No Room For Squares"

  1. Gordon Gecko is pure Hollywood.

    No Wall Street trader would ever be caught with a pocket square, pinky ring, or expensive jewelry.

    The HuffPost has a guide to dressing for Wall Street:
    https://youtu.be/tQtO9fQq_OM

  2. When I worked in finance – I left it in 2004 – lots of people in NYC wore pocket squares. And nobody (well, no men) really noticed them. Ties were a different matter. I used to call it the “tierarchy.” You could easily tell where someone fit into their organization’s pecking order by the ties that they wore. GMs of hedge funds? Hermes. The next level down? Zegna. The guys in the basement who ran IT? JoS A. Banks. And they were proud of the deals that they got. “You wouldn’t believe it. I only paid $25 for this tie!” When I needed to visit the IT guys, I’d actually change my tie, and was always accepted as being “one of them.”

  3. I remember walking into a Georgetown boutique one time and pronounced Hermes as “Air May” instead of “Air Mez.” The proprietor looked at me like I had just let one rip.

  4. Vern Trotter | April 14, 2021 at 7:36 pm | Reply

    I do not believe you can say with any authority that any person will or will not wear a pocket square, type of ring or watch/ jewelry. Certainly in or around what passes for Wall Street, Madison Avenue and corporate life these days. It looks as it is pretty much anything goes. You are watching what you say and being careful not to offend anyone.

  5. Trevor Jones | April 14, 2021 at 7:55 pm | Reply

    Another great column, Prof. Caplan.
    I love the close attention paid to an oft-overlooked detail. The pocket square is something I’ve never felt comfortable with, but have recently made an attempt to try incorporate more frequently into my wardrobe. Taking my cue from the great Luca Rubinacci who suggests laying the square flat, pulling it up from the center (so it resembles something like the Eiffel Tower), and then folding it in half with the “odd” (pointed) side coming out of the pocket. It adds a great amount or flair to an otherwise complete ensemble, and this particular fold allows for a different result every time.
    On another note, I appreciate how clearly you make it that clothes DO NOT confer values. See “Stone’s comments represent one of the least attractive aspects of discussions of traditional men’s clothing: the tendency to assign dubious class distinctions to particular items in order to disparage those considered déclassé. Note, for instance, how Stone describes ‘working class’ as synonymous with ‘tasteless, base, crude, ignorant.’”, “The Duke of Windsor was a dazzling dresser and an otherwise unpleasant human being. His example shows that sartorial style should be admired for what it is, for the skill and flair it demonstrates and the pleasures it gives, and not for what it is not, as a marker of objectionable values.”, or even, “They present a playful little mystery and suggest, at least to me, that clothes might be best enjoyed for the pure fun they bring into our lives.” It should hardly be surprising that the most intelligent contributor here is the one who points this out. Regardless, it is quite a refreshing and welcome perspective.
    Thanks again for another well-written, spot-on piece!

  6. Richard E. Press | April 14, 2021 at 8:45 pm | Reply

    Flusser may have consulted on the original Wall Street movie, but J. Press clothed Ivan Boesky upon whom the Gekko character was based. Ivan’s breast pockets were naked so when he got out of jail he wasn’t handed a kerchief.

  7. Minimalist Trad | April 15, 2021 at 1:56 am | Reply

    Colorful pocket squares call to mind bit loafers. Need I say more?

  8. Old School Tie | April 15, 2021 at 8:40 am | Reply

    I have plenty of other stuff to put in my breast pocket, namely reading glasses. I usually pop my face mask in there too when I sit down in some bar to imbibe. It can look a bit like a pocket square in certain light and from some angles.

  9. Not surprised Johnson cared so much about his pocket square. He certainly thought a great deal about his bunghole when ordering pants.

    Cheers,

    Will

  10. Robert Archambeau | April 15, 2021 at 8:49 am | Reply

    To take fashion advice from Roger Stone (and I leave politics aside here) is to take fashion advice from a man who aspires to look like a cartoon villain.

  11. I confess that I am clueless about pocket squares. It has always seemed like adding a square was one too many colors or patterns to coordinate. I think my tendency to wear somewhat bold ties is part of the issue. It would be much easier to incorporate one with the plain (and dull to my eye) black knit tie from the other day.

    And I absolutely agree with Professor Caplan’s views of the prince and the pol and drawing conclusions from style choices.

  12. I’m obsessed with pocket squares.

  13. Charlottesville | April 16, 2021 at 12:17 pm | Reply

    Thank you, Prof. Caplan, for another fine contribution. While decidedly not an admirer of the character of the late Prince of Wales or of Mr. Stone, I am a fan of the pocket square, from the paisley puff of silk in the breast pocket of a tweed coat to the thin, white slash of the TV fold with a suit or blazer. Like suit trousers without cuffs, a coat with a naked breast pocket just looks unfinished to me.

    And after some dealings with Wall Street investment bankers in the 80s and 90s, I can endorse the view that they did not much resemble Michael Douglas’s character in the film. The potty-mouthed braggarts in department-store suits, obsessing over money, as described in Liar’s Poker, are closer to what I remember, although of course there were many exceptions.

  14. Henry Contestwinner | April 16, 2021 at 8:14 pm | Reply

    I have heard the Duke of Windsor described as “vapid,” but never as “unpleasant.” Was he? He was of low moral character, to be certain, as attested by his repeated affairs with courtesans and married women. Was he a Nazi sympathizer? Based on what I’ve read, he likely had no interest in the politics of Nazi Germany beyond its utilitarian application as a bulwark against Communism (he met Hitler in 1937, so we look upon that meeting with post-WWII hindsight). But was he unpleasant? I’m not aware of contemporary accounts describing him that way.

    Regardless of his personal shortcomings, man, could he dress! Although he tended towards dandyism, he had a style that few can match. Of course, it helps that he had enough wealth to wear bespoke clothes of the highest quality, but even if his means had been more modest, he still would have looked great.

  15. Henry Contestwinner | April 16, 2021 at 8:19 pm | Reply

    Oh, and lest I forget, I, too, am an aficionado of the pocket square. I always have one in my breast pocket when wearing a tie. While most of mine are silk, I have a couple of vintage rayon squares, too. I also have many cotton & linen squares, but those go better with suits, and I mostly wear odd jackets these days, though a blazer sees its way onto my back once or twice a week. I find I just can’t bring myself to wear anything but a white square with a blazer, so the colorful patterned cotton & linen squares in my closet languish for now.

  16. I must confess a fascination with Turnbull and Asser pocket squares-all absolutely gorgeous creations. I have purchased enough to last a lifetime. But I certainly understand they might not be for everyone. Dress must be comfortable and fun without being cartoonish.It is possible to overdo anything so use common sense and good taste should follow. Hopefully.

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