Many wealthy people (and the people that advise or . . . ahem, surround them) wear bow ties. It is important to sort out your feelings on them because the bowtie sends a mixed signal – and there will almost certainly come a time even YOU could end up in serious bow tie jeaopardy.
First of all, there is nothing WASPy or particularly “wealthy†about the bow tie’s origin.
Bow ties were originally used by Croatian mercenaries in the 17th Century to keep their shirts closed. Then the French dandified them and turned them into Cravats in the 18th and 19th centuries. Emily Post only mentions bow ties once in her etiquette book in the 1920’s and it’s in conjunction with black tie wear. In the intervening years since the Depression, bow tie aficianados have split into two camps. Doctors, waiters and chemists wear them for good reason – their professions involve the possibility of spills.
However, bowties have also become an appendage of academics, trust officers, lawyers who want to seem like academics, confused politicians, attention-seeking commentators and people with desperately banal personalities. Tucker Carlson describes wearing a bowtie as wearing a middle finger on your neck. Warren St John had an interesting comment about them in The New York Times: “To its devotees the bow tie suggests iconoclasm of an Old World sort, a fusty adherence to a contrarian point of view. The bow tie hints at intellectualism, real or feigned, and sometimes suggests technical acumen, perhaps because it is so hard to tie. Bow ties are worn by magicians, country doctors, lawyers and professors and by people hoping to look like the above. But perhaps most of all, wearing a bow tie is a way of broadcasting an aggressive lack of concern for what other people think.”
They are not a mark of achievement or leadership- they are a medal that one awards one’s self for individuality.
Bowties are best used when black tie calls for it, by pediatricians that don’t want to be choked by their unknowing patients, or by (deep) southerners in conjunction with khaki poplin or seersucker suits. I have many friends that wear them socially. That works fine as long as they have the personality or personal accomplishment to support such a statement- some do, some don’t.  that said, my prejudice is that during daylight hours, they shouldn’t be worn by anyone that has to work for a living . . . if at all.
Bowtie wearers don’t do themselves (or their spouses) any favors by wearing bowties in public. Paul Simon, the esteemed senator from Illinois, ran unsuccessfully for President back in 1988 and his bowtie was a focal point for his campaign. It became the butt of jokes on Saturday Night Live and ended up overwhelming a talented public official. In fact a study was conducted where people were shown the same picture of Simon- one with the bowtie and one with a regular tie. The picture with the regular necktie had a substantially better approval rating.
Question: Which one would you marry?
In business settings, bow-tie wearers are to be treated with maximum distrust. They want to be seen as mavericks. They like to be right and they like to be experts without responsibility for production. They find comfort in the arcane. However, since they aren’t responsible for producing anything, they are quick with the “no†and rarely provide alternative solutions. Ask yourself how many successful people (business or otherwise) wear bowties. An expert without actual experience, the bowtie wearer will tell you how things should work, but not show any interest in actual results.  As long as they are surrounded by competent people or comfortable surroundings (like a rich spouse or trust fund), this misgiving can be masked for years.
Additionally, when the pressure of expectations hits, beware. The instant the novelty of the bowtie wearer itself wears off, insecurity ramps up. As John D. Spooner related in the Atlantic : â€Men who wear bow ties care more about themselves than they do about you.” This can lead to all sorts of issues (infidelity, ethical lapses in business etc . . . ) and if the money runs out, remind yourself how this person became wealthy in the first place. There are no second acts for bowtie wearers.
Remember this going forward. Only, in the rarest of the situations will the super-wealthy wear a bowtie. Invariably, they are not concerned about others’ opinions of their individuality (or relevance). They are busy building or maintaining their wealth.