Top Ten Reasons You Should Dress Like Old Money

I constantly encourage people, in conversation and on this blog, to adopt the Old Money style of dressing. Why? First, it’s an easy, affordable step to take on the road to becoming an OMG (Old Money Gal or Old Money Guy.) Second, it begins to create distance between you and the retail advertising merry-go-round that constantly promotes the “latest style”, “what’s trending”, and “this season’s must-have’s”.

The latest Old Money style has been trending, season after season, since the 1950’s, without much change, as you’ll note in the photo below from the Ivy Style blog. Young men today could be clad in these same garments and still be considered well-dressed. Actually, some are. (Wink, nod.)

Ivy Style 1950s

There are other reasons to adopt the Old Money style of dressing. Conveniently, they seem to have arranged themselves into a TOP TEN LIST.

Here we go:

1. Old Money Style is a value…although it may not always be cheaper. To dress like Old Money, you choose traditional, quality clothing and shoes that will endure both the whims of fashion, frequent use, and the passage of time. That means you buy fewer items of generally greater quality than most consumers. OMG’s spend money on their shoes. Well-made shoes, with proper care, can last a lifetime. So it’s a good investment. The same goes for your articles of clothing. I recommend Mercer and Sons shirts, Allen Edmonds shoes, and Brooks Brothers for a navy blazer and khakis. Smart purchases from these vendors will get you started and keep you going for decades.

2. It reflects a set of values. I’ve discussed in other posts on this blog how we dress to impress others as well as to designate our membership in, or desire to be a member of, a certain social “tribe”. Dressing like Old Money, i.e., wearing traditional garments without drawing unwarranted attention to yourself tells others that you are, or aspire to be, a member of the Old Money tribe. That’s not a bad thing when it comes to presenting an image to potential employers or potential in-laws. To put it more bluntly: you may not be reliable, trustworthy, professional, or competent, but you might get ahead dressing like you are. Just a thought.

3. It’s polite. These uncertain economic times.  Many people are having a challenging time getting an education, paying for that education, finding a job, keeping a job, feeding their family, and saving enough money for retirement. Do they really need you to fling the bling in their face? No, they don’t. Dressing ostentatiously creates resentment, and it doesn’t really impress anybody worth impressing.

4. It’s a no-brainer. Some people, many of whom seem to be Italian or French for some reason, have a natural finesse, a care-free elegance with clothing. They easily and instantly throw an outfit together and look great. If you’re not one of those people, and most of us are not, then it’s best to bet on the go-horse and forget the show-horse. Stick with the basics. I’ve outlined them in detail in the How Old Money Does It section of The Old Money Book.

5. No embarrassing photos ten years later. Every decade has its fashion debacles. Don’t be a victim. Dress traditionally. Keep the hairstyles simple. Easy on the mascara. It will spare you pain and suffering later on.

6. It’s easy to dress up or down. For men, the Old Money style anchors itself around a white or blue oxford cloth button down shirt, a pair of khakis, a blue blazer and a pair of brown leather shoes. If you remove the blue blazer, you’re dressed for a baseball game. If you add a neck tie, you’re dressed for a wedding. It’s no less simple for women.

7. It travels well. When you get ready to pack, the versatility and durability of your garments are key. Classic clothes tend to easily mix and match. They also tend to be easier to take care of on the road. You can pack less and have more options when you arrive at your destination.

8. It’s okay if it’s worn and old. Old Money prefers Old Things. If you’re khakis are frayed and your sweater is unraveling at the elbow, so what? Just keep your clothes clean and take care of them. Relish the wear and tear.

The Boston Cracked Shoe Look, worn with pride.
The Boston Cracked Shoe Look, worn with pride.

9. It’s comfortable. High fashion is great, but you don’t want to take a transatlantic flight in an evening gown or a tuxedo. Traditional clothing is, by and large, comfortable to wear. Natural fabrics (cotton and wool), a fairly unstructured silhouette, and a cut that’s not too loose and not too tight define the style.

10. Nobody will know how much money you have. If you don’t have a lot of money, people will note that you have good taste. If you do have a lot of money, people will note that you have good sense. In this digital age where so much information is available to so many people about so many people, dressing like Old Money will convey a sense of mystery. And that is a rare and attractive thing these days.




9 thoughts on “Top Ten Reasons You Should Dress Like Old Money

  1. Hello, Byron!
    I’ve been enjoying your blog (and, of course, your book.) My parents raised me with many of the same values that you propose in The Old Money Book, but I never gave much thought as to why. I suppose that I chalked it up to European idiosyncrasies. Anyway, it was a great read.
    I will preface my question by saying that this may be a more appropriate query for your wife (or other OM gals in your acquaintance) but here it goes…
    In the clothing section of the book, you write about the classic sheath/ shift dress for women (sleeveless, crew or boatneck, black, among other colors.) Where does one find such a dress? Really. I thought that such a classic piece would be easy to find but I have looked high and low… online, in stores- from inexpensive big box retailers all the way up to fancy-pants New York department stores. I can’t find a classic black sheath dress that isn’t too short, doesn’t have an odd neckline, a plethora of pockets, or isn’t littered with hardware. I’ve even inquired into the possibility of having one made but my seamstress is buried under a mountain of wedding dress alterations.
    I’ve started thinking that the fashion world is too fashion forward these days to give any consideration to classic pieces. Anyway, I would be most grateful for any guidance you, your readers (or any female acquaintances) could offer on the subject.
    Merci bien!

    1. Bonjour, Lenka! Thank you for the inquiry. It is difficult to find classic dresses and clothing for women in the retail environment. Your frustration is shared by many Old Money Gals, and I welcome suggestions from any who’ve read your comment. You might try this: find a photograph of the dress you want. Try to locate a pattern for it online or at a fabric store. At your local fabric store or dry cleaners, especially in OMG neighborhoods, the proprietors probably know a seamstress or tailor who can make the dress for you just by looking at the picture, and certainly by working with the pattern.

      You would supply her the pattern, fabric and any buttons or zippers for the construction of the dress, jacket, or pants. She would supply the expertise. The seamstress should be able to provide references of happy, long-time customers. If possible, meet them, see how they’re dressed, and see if you like the quality of the work.

      This isn’t the quick-fix retail experience of seeing it & buying it in 15 minutes or less, but you will have a garment that fits you perfectly, lasts for a long time, and never goes out of style.

      Something to think about. Please keep everyone updated with your thoughts and progress on this. I know it’s a challenge. Thanks again! – BGT

    2. Bonjour, Lenka!

      I have had decent luck finding such dresses at L.L. Bean, J. Peterman, and, lately, at eShakti, which I tried because I was having a dreadful time finding dresses in below-knee lengths, and they give you the ability to customize practically everything about the dress, from neckline to length to sleeve style. I tend towards fit-and-flare styles, but the sheath dresses from the above retailers are also lovely.

      Je vous souhaite de bonne chance en trouvant des robes!


  2. Another advantage of dressing in this manner is the ability to focus on what you love to do without worrying about looking presentable. It’s a uniform that you can put on and forget about.

  3. Yes, I also agree with Mary. A well made pair of black pants (or any neutral color) for women and a beautiful shirt (blouse) looks classic and timeless and allows you to focus on what needs to be done rather than constant worry if you fit in fashion-wise.

  4. Greetings to you Byron, from Neuquen Argentina.

    I was just idling through the above page and noticed the photograph of a set of well polished toe-caps.

    If I am not mistaken those feet belong to H.R.H. The Prince of Wales (?) I believe they’re a pair of John Lobb’s and a must be cracking on for forty years of service. Just starting to get worn in.

    That’s a good example of a sensible purchase, if ever there was one.


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