Old Money Style – An Update

In response to a couple of emails that I’ve received lately, I just wanted to give everyone a quick update on the Old Money wardrobe, as it continues to be a topic that interests people. (Good.)

That’s completely understandable, as the way people dress may be the most visible and obvious expression of their identity, if not their beliefs. It is probably a ‘key indicator’ in many instances.

So let me just touch on some familiar but important parts of dressing Old Money Style that will confirm for our Members of the Tribe and clarify for some of our new readers.

First, view clothes as an investment, not an expenditure, and certainly not as a ‘statement’. You’re not trying to impress anyone in an obvious way. Dressing like Old Money will impress them, but in a more subtle and gradual way, but only if your performance, speech, and manners support your image.

As an investment, you’re going to opt for traditional/preppy/Old Money style (which doesn’t go ‘out of style’), natural fabrics, versatile garments, and quality construction. You’re going to buy garments that you wear every day first. You’re going to buy garments that you can wear for several different occasions (office, weekends, weddings, etc). You’re going to buy garments that you can easily mix and match.

If you can dress preppy from cradle to grave, do so. You will save yourself time, heartache, and money. Depending upon your budget, you can assemble a wardrobe from Ralph Lauren, Brooks Bros, Lands End, and LL Bean with relative ease. (Tribe members, add other vendors in comments if you wish, please!)

The trick will be getting the most for your money. That means acquiring garments that look good and ones that last. Comfortable options are cotton shirts or blouses in white, blue, or blue and white stripes, khakis or solid color cotton pants, grey wool pants, corduroys, penny loafers or Topsiders, solid color wool or cotton sweaters…these are the fundamental pieces that most people can wear every day and look good.

The blue blazer remains a go-to option for dressier occasions, and not just for guys. The navy blue suit with a not-too-tight, not-too-loose cut and traditional style is an eternal, fundamental piece at some point in time.

The fine line may be to look like you care, but don’t look like you’re trying. Also note that if you get rid of all the ragged T-shirts in your drawer or closet, you won’t have any choice but to throw on a polo pullover…and look much better in the process, without any more effort. (Keep the logos small.)

An imaginary exercise for your garment and color choices is to pretend that you open your closet in the middle of the night, pull out all the garments you need to be fully dressed, get dressed in the dark, then turn on the light. If you’ve curated your wardrobe well, almost anything will go with anything and look presentable…

Avoid the shopping mall, if they still have those. Look online. Shop at traditional clothing boutiques like McConnell’s of Buffalo, New York, or J Press. Only shop two to three times a year. Watch for sales. Avoid trends. Avoid synthetic fabrics, except with rain gear, of course.

And remember, Old Money style whispers. Old Money style endures.

  • BGT


19 thoughts on “Old Money Style – An Update

  1. J. Press, Mercer & Sons, The Andover Shop, L.L. Bean, and (for the ladies) Talbot’s and Ann Taylor. Can be a bit pricey in some cases, but watch for sales and end of season clearances. Certainly an excellent return for the investment. In any case, have minor alterations made by a tailor or seamstress, so that the items fit perfectly and flatter the figure. It’s amazing what taking in half an inch to an inch will do to improve the overall look of a garment. Well worth it.

    Kind Regards,


  2. This article came out at just the right time.

    This comment may seen strange, but here goes. I am new to this, but not. When I begin thinking back to my middle teens, I really did like the old money/preppy style. However, it has taken me longer to realize it is a style I am most comfortable in dressing.

    I believe most on this blog love to dress well, as well as dress *smart* I say this because there is nothing like looking well dress and put together for the public to view. Not that we would feel snotty for dressing in this manner, but feel as though we reached a plateau of dressing beautifully!

    So much so, we could with the lights off, take anything out of our closets and look put together with little effort.
    (I actually might try that!)

    Though this is still a learning curve, I thank all in the comment section and for the many articles written which help me think of clothes as an investment in my journey.

      1. Wanted to share…

        Tracy (𝒞𝒽𝒾 )
        2. Delta airlines just said today that they expect 2.5 million travelers this memorial day weekend, which is up 25% over last year.
        3. If you take a look at retail earnings, people are spending money on travel rather than “stuff”

  3. I think this comment may be controversial but I kind of intend it to be: I believe there is more beyond “preppy” style while living up to and applying the old money principles. Here’s two points I think are worth considering:

    1) Prep is dead. Prep remains dead. And we have killed it: Preppy clothing in 2022 USA carries a certain political aloofness and out-of-dateness that shouldn’t be ignored. It is associated with the Republican Party, American Exceptionalism, and Xenophobia. While Old Money is by definition an extension of its lineage and pedigree, someone in their 20’s would stick out to the point of negative notice in this day and age (and does in my experience). Not ideal while wanting to advance professionally and socially (I can also speak personally to working in the Bay Area in the financial services industry: dressing too prep could come across as out of touch with the tech industry and millennials+ and make it difficult to build trust and relationships. I was specifically told to not wear jackets or ties while visiting client sites in San Francisco).

    2) Prep is not the only style which old money principles can be applied to: I am from Oklahoma. I went to a private college in Boston. I have spent my professional life in NY and San Francisco. I have spent the majority of these years in t-shirts, jeans, flannels, chambray shirts, and moccasins. I have focused on quality and longevity and timeless style, and been known as well-dressed amongst my friends while personally knowing I get tremendous value out of my wardrobe. I have also applied old money principles to every purchase I make: Workwear has been worn for over a hundred years, just as long as standard prep, so there’s no concern over going out of style (prep however, is at its cultural ends). It is heavy duty and will last several years. Often, the artisanship is tremendous and workers are fairly compensated. The clothing develops individual character over time. I believe there are so many similarities to the attributes of prep among other styles. But most importantly, clothing and style are very personal topics and I think to say to live a life led by Old Money principles only results in one specific style could be accused as narrow and closed-minded. Just look at the differences between old money style abroad vs. American Old Money style. Surely there is more than one camp in the US that applies these principles?

    I hope you all will thoughtfully engage this idea and be open-minded to how Old Money develops over time. I think the key here is to be sure that the Old Money principles are not compromised, not that Old Money dresses the same for 100 years. My two points were just one example of why there is life beyond prep, but I would love to hear other examples that apply old money principles. After all, fashion IS a beautiful art form and I think the history of fashion has given us more value than we give it credit for.


    1. Thank you, Bryce. We have a tradition here of welcoming ideas that are controversial or contrary to the status quo, especially when they’re articulate and thoughtful. So your perspective is much appreciated and the nuances you highlight are definitely things to be considered by our readers.

      A couple of thoughts, in response to yours…first, the co-opting of ‘prep’ or Old Money style by a certain political demographic is an issue, especially for those of us who prefer to wear khakis, button downs, and penny loafers, and don’t hold extreme/hateful/racist political views.

      I think there will be a sartorial/cultural tug-of-war in the coming years, but the extreme right doesn’t get to monopolize Ivy League style (let’s call it) that has been the wardrobe of Republican investment bankers and Democratic Harvard professors alike for almost a century. Dressing the way we do is a cultural marker that belongs to us. It is indicative of Old Money values, not a costume for ignorance and prejudice to masquerade in as icons of tradition, heritage, or patriotism. It is certainly not an ensemble to be worn with an attitude. Quite the opposite, actually. Posers will come and go. We will remain.

      Second, I might have made a mistake by equating preppy and Old Money Style. To me, they’re the same thing, but I think to others (younger), one might come across as distasteful. When someone who dresses OMS walks into a room, you may notice that they’re well-dressed…more than exactly ‘how’ they’re dressed. Perhaps preppy is a little more obvious.

      Finally, we are a generation apart, Bryce. My perspective is obviously different. While I am not old, I do have experience. I watch elected officials appear in public, conducting official duties, without neckties (men) or wearing jeans (women). This surprises me, and not in a good way. Our attire communicates volumes. Clothing often shapes our behavior in ways we may not always be aware of. Often, our attire corresponds to the amount of respect we have for an event, an institution, or another person. Sometimes the two are not related.

      Food for thought, as they say. I appreciate you sharing your experiences regarding the current ‘lay of the land’ in your industry as it relates to wardrobe. I hope other readers will share, as well. – BGT

      1. Hi Byron, thank you very much for your candid response. I really do appreciate and value the dialogue on this page and hope to continue having meaningful discussions with the Old Money community for years to come.

        I 100% agree no political faction can claim a style that arguably is the foundation of Americana clothing and style. I do wear OCBD’s and chinos on a weekly basis, maybe just spiced up a little bit by combining with other elements of Americana. There actually already is an ongoing debate over where prep stands in American culture, especially around diversity and inclusion. I think the bankruptcy of J. Crew and Brooks Brothers also shows the shift in style and culture.

        I also agree that clothing is one of the most important ways we communicate our values to others. I should have added that although my dress is inspired by my upbringing in ranch and oil country, I still wear tuxedos from a tailor and get custom suits for weddings, as I believe in dressing to respect the situation, as you mentioned. I do however, think that casual clothing gets a bad rap because the individual most likely to lounge about in t-shirts and jeans is not concerned with fit and quality, the two most important aspects to clothing IMO.

        I may have been unfairly harsh to prep, but the main point I wanted to drive though is to request a seat at the table for the next generations that are inspired to live a simple, elevated life inspired by Old Money principles while allowing them to make their own cultural impacts on history. I think having the discussion of how the Old Money look will change over time will encourage younger generations to join the conversation. Just like how we don’t wear three-piece suits to the office (if we ever go these days) like our grandfathers did, my children most likely won’t wear polos and boat shoes to school. They WILL however, be taught to focus on fit, quality, value, and timelessness.

        Thanks again for the dialogue Byron, I always look forward to your posts.


      2. Much appreciated, Bryce. It’s great to hear your perspectives. The next time you’re in Paris, we’ll have a coffee. Thanks again. – BGT

      3. I’m late to this, but here goes.

        This caught my eye: “I may have been unfairly harsh to prep, but the main point I wanted to drive though is to request a seat at the table for the next generations that are inspired to live a simple, elevated life inspired by Old Money principles while allowing them to make their own cultural impacts on history.”

        The one thing that I see in OMS is precisely what you say: simple elevation. This leads to two things.

        But before going in those, let’s agree that a good piece of clothing is such that it stands the test of time… in terms of both material/construction quality as well as psychology. Psychological obsoletion is key here. So, what follows is…

        First, you can’t really change too much in the style. Timelessness requires this. You can of course select differently within the context, as you do. You can choose to go without a tie, but you can’t opt for a baggy tee with a loud (or worse) print. That would definitely not be OMS anymore. So, there are only so many ways that you can wear anything that’s timeless in both construction (incl. material) and style. What changes might be the cultural fit. That is, while you’re not required to wear a suit for work anymore, the things that you will wear, were a part of the style even decades ago. Just not for work.

        Second, you can change something. Jeans are a (relatively) new thing in this context, but even in today’s laissez-faire environment, not all jeans qualify. There is a continuum, and jeans are accepted not because of some big shift in culture, but rather because jeans have changed up to the point where they can be accepted. (Of course all sorts of monstrosities are accepted these days, but they can hardly be described as OMS or any other related term).

        I think I’m saying that I agree that the style is and must be allowed to evolve, as all things cultural do. The generations will leave their marks, but there can only be discussion between the generations if there is some common understanding. Otherwise it’s just tearing down the old, which is the exact opposite of timelessness.

  4. The Uniform is my go-to work from home style anymore. Unlike my former style of wearing whatever I had laying around — usually jeans and a fleece pullover — The Uniform puts me in a serious working mindset every day. And, I am always ready to hop on a video call or answer the door.

    The Uniform also enables me to pop outside to run a quick errand without having to “get ready.” And in my non-white, non-Western adopted country, where most people respect and admire the “Ivy” look, I get approving looks and smiles from shopkeepers and passers by.

    Thanks again, Byron!

  5. I have to suggest G.H. Bass Weejuns, and Allen Edmond for great footwear. They are dressier than Sperry Topsider, but great investments. Excellent addition to this great list.

  6. I was a flannel shirt, football jersey blue jean wearing knucklehead until my college girlfriend (didn’t last) introduced me to prep clothing. She was a prep from her club collars down to her duck boots. Her father a bank v.p. was ivy all the way and although I didn’t know it at the time the family was seriously old money. One house, drove cars till they died, but always always bought quality. What they really taught me was to buy well and buy once. I never forgot that. Here is my confession, thrift stores. Many thrift stores, especially those associated with charities (hospitals) have wonderful quality clothing at an absolute fraction of the price. Recently I found a spring weight BB blue blazer and a three button linen sport coat both in my size….$8, each! It’s a very economical way to build a wardrobe if you know what you’re looking for. When our two sons were growing and needed a jacket for communion, confirmation, grade school graduation we would “rent” one from a local thrift, they would wear it, then their brother and we would then return it to the same thrift store to be sold again!

  7. Hi Byron,

    I asked a question about purchasing a luxury watch a couple of weeks ago, on an old post from you about the JLC Reverso. I would very much like to read your opinion on that subject if you have the time? Is it better to ask questions on your new posts instead, perhaps you don’t see comments on the old ones?

    Many thanks in advance Byron! 🙂


  8. Such an interesting discussion on how dressing in a classic style has been co-opted by the extreme right. They seem to have co-opted God and the word Patriot too. They only get to keep them if we let them.

    I work at a university the Rocky Mountain West. The students are incredibly casual, the faculty much the same. What I do notice is that a polo shirt and a pair of jeans that fits rather than is trendy looks better than over-baggy/over-tight versions but the person doesn’t stand out from their peers, they just look neater. I dress in a female version of prep because it’s easy and comfortable. House of Bruar cotton shirts are incredible and their Liberty versions are stunning. They are cotton with a normal fit rather than a mix of spandex with some sort of fashion fit.

    I don’t think J.Crew and Brooks Brothers went bankrupt because of they were out-dated, I think they found themselves in difficulty because they reduced quality, increased prices and forgot their core market. While there may be a number of teenagers and people in their early twenties who can afford to buy J.Crew regularly on their parents’ dime, real-world salaries probably don’t allow them to. They both lost those of us who like quality and have more disposable income.

    I notice that the majority of charter schools in the area have a uniform of polo/button-down and chino shorts/trousers/skirts. It’s neat. Doesn’t require too much work. No dry-cleaning needed (unlike my 100% wool tartan skirt from Catholic school). It’s also affordable with price points at levels for most incomes.

    Having worked in the software industry for 15 years before my present role, there was a snobbery within that industry too. The engineers dressed a certain way (definitely not preppy), the marketing people had to be hipster cool, the business-facing salespeople dressed in business casual – I cannot count the number of blue shirts worn. We had a mix of people from the Bay Area and New England – both looked down on each other for their way of dressing.

    There is classic and there is fuddy-duddy. There is a difference. Every few years, there is a tweak in a silhouette that can be incorporated. No-one stands out, no-one looks like they have gone through some kind of style make-over that is so popular on reality tv. Most people can get on with their day without having to change into multiple outfits unless exercising or doing to a black-tie dinner. Older versions that have been worn more often move from weekday to weekend wear. Also, the basic principle of this style allows for a certain dash – colorful socks or ties, very wide stripes in shirts, mixing in modern jewelry for women.

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