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Top ten reasons you should dress like "Old Money"

Dress traditionally. Keep the hairstyles simple.

Article contribution by Byron Tully

Photo: Andrea Riom (credit: @andreariom)

I constantly encourage people, in conversation 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.)

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.

Photo: Andrea Riom (credit: @andreariom)

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.

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.

About Byron Tully (right)

Grandson of a newspaper publisher and son of an oil industry executive, Byron Tully is an author who also writes for the entertainment industry. His nonfiction debut, "The Old Money Book," was published in April of 2013 to excellent reviews and enjoys consistently strong sales worldwide. His other works include "The Old Money Guide To Marriage", "Old Money, New Woman: How To Manage Your Money and Your Life", and "Old Money Style - The Gentleman's Edition".

Byron regularly contributes to its blog, www.theoldmoneybook.com, which has been visited by over 1 million readers since 2014.

In February of 2020, "Old Money Style - The Gentleman's Edition" was published by Acorn Street Press. This fourth book in the Old Money series reveals the fundamentals of dressing well in a classic and timeless style. In November of 2020, Byron published a 2nd Edition of "The Old Money Book", which expands on his original classic. This 2nd Edition includes vital information and insights for readers as they navigate a very different, post-pandemic world.

Byron speaks frequently about the culture and values of Old Money. He has been interviewed by KABC New York's Financial Quarterback Show, The Huffington Post, and The Simple Dollar, among others.

He lives in Paris and is happily married to an Old Money Gal from Boston.

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