why I loathe the term preppy · Real Men Real Style Community

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why I loathe the term preppy

Recently

had me speak on a zoom panel about my style journey where I stated my disdain for the terms preppy and old money. Antonio even called me out on it since he has done videos about each term. While I tried to stay on task for the limited time I had on that call and sidestepped his comment, I thought I might take this opportunity to elucidate why I dislike those terms so much. And far be it from me to speak out against Antonio whom I deeply admire. Hopefully this might clear up any misunderstandings about what I mean. Anyone who has read my stuff here for a while, probably knows that I loathe both the terms preppy and old money. Oh believe me, I get where they come from. And a part of me is pleased that there is a movement for guys to recognize the classic aspect of each’s appeal. But to understand my issue with the terms let me provide a little background first. Born in 1960 I grew up in that decade as a small boy. Naturally I was a TV kid. On television, hair styles and clothing styles were pretty standardized (think Flipper, my three sons, leave it to Beaver, I dream of Jeanie, Bewitched etc etc. Some of the youngest members of this community will need to do a google search i suppose). By the late 1960’s and into the early 1970’s there was a war waging in jr highs and high schools across my state regarding school regulations about hair lengths, tshirts, torn and worn jeans (and that’s just the boys. The girls brought on a whole new dimension regarding skirt lengths etc). My bank president ex Airforce father and I had our moments as my hair became an inverted bowl, all my t-shirts graphics were heavily scrutinized, and my blue jean waistbands got lower while my legs flared out more and more. By the time I reached college in 1978-the nightmare that was the 70’s was in full force. Yet because I worked in men’s clothing, I at least had begun wearing quality shirts to school (Gant was a great brand in the 70s) and Berle (khaki trousers) that we sold. By the third store I worked in, most gentlemen had finally ditching the nightmare that was the 70’s and one of, if not the biggest influence was Ralph Lauren (which we sold). By 1980, natural fabrics and classic designs were taking back menswear by a storm. Then the damn book came out. Because Harold’s (the store where I worked) was specifically mentioned in that confounded book (The Preppy Handbook), Not only did we sell the book-we would sell out every crate we received in just a few days. Worse, each of we clothiers read our copies cover to cover because the clientele expected us to be experts on all things in that confounded unholy 🙄scripture (we were on commission after all). No matter how much we would tell people it was only a parody-most people simply didn’t get it. There were kind of two types of clientele. The guys who wanted to look good. And the guys who wanted to chase the latest pastel (provided it at a horse on it or Ralph’s name on the tag.) The sad part is Ralph became popular because of its superior product and design. But the craze took a life of its own. Sort of like a swarm of sherbet madras zombies chanting preppy instead of brains . Of course I am being flippant. Truthfully as a guy at the very tail end of the boomers I was helping most of our clients who were buying this book (essentially slightly older boomers ) who had been duped by the absurd fashion trends of the 1970’s and were eagerly searching for merely some return to sanity {hmmmm sound familiar to today perhaps🤔}. Yet many didn’t really understand what they were running to -as much as what they were running from. This reversal of the disco double knit platform shoe nightmare of the hideous clothing known as the 1970’s flipped to some kind of traditional menswear and the rapid change was world wide. Then a strange thing happened by the 90’s. School aged kids began to wear classic Ivy clothing but did so in many cases as a status symbol. Naturally this produced cliques and commensurately caused counter cliques to wear the antithesis of “preppy”. Let me explain further. While clothing fashions has always been characteristic of different social groups especially among teenagers-I submit that the multiple groups like preps, goths, cowboys, hip hop, mall rats, geeks, etc etc took on a whole new dimension from the 1990’s on, perhaps until today. (In my high school we kind of had only three: stoners, goat ropers, and everyone else).

Bottom line is this -Classic Timeless Menswear- especially the Ivy League version of that, has a storied 120 years of history (some could argue longer than that if you count its source Brooks Brothers founded in 1818). It’s proven elements have been the foundation of American Classic Timeless Menswear just as Savile Row has been the foundation of English Classic Timeless Menswear. Preppy on the other hand stems from a throw away term in a 1969 book/movie (Love Story). Plus a parody made to make fun of a group of people in a paperback book (The Official Preppy Handbook written in 1980). There was a very prescient interview 30 some odd years ago with the then President of Brooks Brothers where he stated that he hated that term preppy and he predicted that it would lead to severe problems for that firm. What he meant by that was by reducing Brooks Brothers classic styling to a “fashion trend” it reversed the “timelessness” of their proven “Classic Style” that Brooks Brothers basically had brought to the world. From the mid 1990’s this reductive mentality (i.e. those are mere “preppy” clothes) it took about 15 years for this icon of Classic Timeless Menswear (as well as the rush to throw away clothing provided by the lowest bidder) to fail. Consequently the concept of PREPPY ultimately contributed to the collapse of Brooks Brothers, the grandfather of the American definition of CTM failed and declare bankruptcy in 2020. (BB had been on its heels- ready for a knock out for some time). Knowing a lot of brothers here are Gen X guys and younger my guess is these terms have a different meaning for you than for me since your high school and perhaps college years were in the middle of all of this. But I challenge you to see through the hype-see through the “fashionista’s” simple understanding of varied looks and understand that the conventions of Classic American Timeless Menswear has a proven history. That means the color schemes, combos, patterns, shoe styles, etc etc can represent an “investment” when building a wardrobe.

This is why a navy blazer as a guys first tailored coat, with grey and khaki trousers and blue white and pink oxford shirts and a charcoal suit make sense for a guy starting out. This why the fit of the garments being non trendy (coat covers your ass and buttons at your waist) makes sense. And then there is the fabric. This why one should buy quality garments in these staples so they can last and be worn in multiple situations for a long time. If one has been through a major weight loss or is a young man (or a gentleman who has never embraced quality tailored clothing before) who is just starting this journey, one should stick with tried and true thinks like rep ties and foulard ties, when venturing out into timeless style. Rely on proven patterns (Prince of Wales, herringbone, houndstooth, pin and chalk stripes etc) that just makes sense.

As a Fiduciary Financial Advisor, I think in terms of cash outlays for everything. Using the term “investment” for an expenditure that loses money as rapidly as clothing is a massive oxymoron. But since we all need to wear clothing anyway, and clothing is that first impression item that exemplifies the idiom used in the Kingsman Movies: Manners Maketh Man - this is the essence of Real Men exhibiting Real Style. Dressing well is respecting oneself as well others-the essence of good manners. Doing so has a remarkably well proven track record for adding wealth. So instead of chasing a fashion thing like “Old Money”. Decide today to become OLD MONEY. It’s not pretentious to wear things that are proven, apply good habits like treating others well, which is also proven, and busting ones ass at work, as well as stop doing idiotic things like spending beyond one’s means paying for yesterday instead of living for today and tomorrow (translates to having a penny of revolving credit card debt). Each of these GOOD HABITS will build wealth. These are all steps to become OLD MONEY.

SO CHIP, BIFF, MUFFY, I’ll see you at the club tonight and we can get BORNEO talking about this-RIGHTEO?😎🤣

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