Old Money vs. New Money – The Clothes

I feel like it’s been awhile since we reinforced (for our loyal readers) and introduced (to our new readers) one of the basics of the Old Money lifestyle: the clothes.

So let me cover some important points that will articulate the how-to aspect of dressing in Old Money style. More importantly, I’ll review the even more important aspect of ‘why’ we adopt this mode of dress, from cradle to grave.

First, let me say this: creating an Old Money wardrobe is probably one of the easiest changes to make when you start adopting the Old Money way of life. You can ditch the cheap, trendy, and flashy articles of clothing you own and reinvest in more traditional, durable, and discreet pieces that are versatile in use and classic in design.

But, unless you’re actively interviewing for a job or have just landed a new job that requires you to upgrade your wardrobe, it’s probably not the most important thing you can do. Higher on the list would be getting a handle on your budget and committing the Old Money Values that I talk about in The Old Money Book to heart.

But I am aware that some people work from ‘the outside in’, meaning that sometimes changing your wardrobe can lead to changing your mindset. And that’s fine. So let’s talk about the basics of creating and maintaining an economical and enduring wardrobe that’s going to serve you well for years to come.

First, the philosophy: the thinking behind dressing in an Old Money or ‘preppy’ style is that you’re not attracting undue attention to yourself. You’re also communicating the idea that you are to be treated with respect. This means, for Old Money Gals, that you’re not showing cleavage with your tops or sporting misdemeanor-high skirts or provocatively cut jeans.

For young Old Money Guys, the look will communicate reliability and an awareness of, if not an adherence to, Old Money Values like The Work Ethic, Family, Health, and Financial Independence, just to name a few.

Second on the list is the economics of the situation. By this I mean that you’re going to view your clothes as investments: things that will give you more use and value over time than the initial amount of money you paid for them.

If you stick with the tried-and-true J. Press/Brooks Brothers/Ralph Lauren/Lands End/LL Bean styled button-downs, khakis, wool and cotton sweaters, and traditional footwear and accessories, you’re going to buy fewer articles of clothing, less often, and enjoy a better overall look over time.

All of your shirts, pants, and jackets are going to go with each other, so you’ll have more versatility–more looks–with fewer pieces.

What you don’t want to do is follow fashion. Instead, develop your style. Avoid credit card debt. Save your money. Be financially independent sooner. One of the easiest ways to do this is to dress Old Money Style with classic pieces, curated over time.

Oh, by the way, economics also applies to the ease with which you can clean, preserve and maintain your wardrobe. Quality 100% cotton oxford cloth shirts and blouses, cotton khaki pants can all be washed, dried, and ironed by you, at home, saving the expense of dry cleaning for most of your daily wardrobe. Dry cleaning can be hard on clothes. Best to use it only for sweaters, jackets, blazers, and suits.

(For guys, check out previous blog posts here or get your copy of Old Money Style. For ladies, I detail your wardrobe basics in Old Money, New Woman.)

Another important point to mention is comfort. Dressing Old Money Style means that you’re comfortable in your own clothes, not to mention your own skin. You can walk the city, hike the country, weather the cold, endure the heat, play with the dog, and attend the theatre…all in clothes that are appropriate for the event and comfortable to wear.

Guys, f you’re not really interested in clothes, Old Money Style is definitely the way to go. You can get your copy of Old Money Style, go to the chapter that details The Starting Five, and purchase the five articles of clothing that you’ll probably need and use most. Bingo, Ringo, you’re done.

Gals, make it easy on yourself: just get your copy of Old Money, New Woman and review the items on the ‘Short List’ in Chapter 12, or simply leave a comment here on the blog, asking for help. Our gang of trusty Old Money Gals will offer suggestions, vendors, and wisdom to help you easily and economically transform your wardrobe.

If you’ve been away from work or out of work for a period of time due to the pandemic, this is your chance to reinvent yourself and reintroduce yourself to the world.

You may be working at a new company, working from home, or working two jobs. Don’t make yourself crazy by trying to assemble a different wardrobe for each new circumstance. Adopt Old Money Style, preppy style, or whatever you want to call it, and make it your own.

It’s a whole new ballgame. Play it well.

  • BGT


25 thoughts on “Old Money vs. New Money – The Clothes

  1. In addition to the retailers you cited, do you consider Talbots to be a source of Old Money clothing for women? Thank you.

    1. Hi Caroline, yes, from what I remember when I lived in the states. Affordable, classic, well tailored. You’ll probably hear from our other readers about this, too, I hope. BGT

  2. Byron-
    I sincerely enjoy being reminded of the OMG classics of “How -To”, however, do to Post COVID, work from home, etc are the basic’s of OMG classic for men still to be applied?

    K. Lee George

    1. Good question, K Lee. Yes. Maybe now without the necktie. One should always be dressed appropriately, ready for an unexpected Zoom call or an unexpected knock at the front door, if working from home.

      Out in pubic, one should always be dressed well enough to be comfortable running into someone important in the parking lot. This could be a potential mate or a potential work colleague.

      Holding up standards not only presents a good image to others, it ups our mental game a little, too, I think. – BGT

  3. In response to Caroline’s comment, Talbots seem to be one of the last few retailers (online/brick and mortar) of women’s clothing that still provides clients with classic, well-dressed options. Yes, they have changed over the years in order to remain relevant in the retail world. Some items look toward grasping the younger demographic but they have remained for the most part, true to their loyal and original clientele. I personally find their clothes classic, well-made and well-fitting. Unfortunately, most women in my age group wear primarily gym clothing (yoga pants, ball caps, sneakers, etc.) which I have yet too understand. Not my cup of tea but to each their own. I like to dress nice and find much enjoyment doing so.

  4. Talbot’s is, in my opinion, the last bastion of classic clothing for ladies. With that said, you still need to be careful as some of their items tend to be ‘cutesy’ – however, if that’s what you like then ‘go for it.’ To be honest, I am not one to judge what others wear. I know plenty of young women from Old Money families that have strayed from the classic look. It’s a matter of personality and expression, sometimes. Curiosity getting the better of me, I read ‘Old Money, New Woman’. Byron, if you think Old Money gals wear only lip gloss and a little mascara then all I have to say is that you have never sat in a board meeting or lunched at the country club with some of these ladies. The secret is to wear it ‘all’, but do it in such a way that it looks natural. It also depends on the geographical areas. Ladies I volunteered with in Dallas were way more dressed up and made up than the ladies in Washington, DC or even NYC, but ALL were extremely polished and none bare-faced. Even now I live on a tropical island surrounded by women of the same caliber, all groomed and not bare-faced.

    1. Kathie, I’m not an OMG, but as a young woman trying to every day be better than the day before, I appreciated that Mr. Tully’s book was the only book of its sort I’ve read that didn’t inform me that I had to wear makeup every waking moment in order to be considered elegant, appropriate, and respectable. Living in the southern part of the United States, there is still an expectation that properly dressed ladies always wear makeup, but I have found over the years that I prefer not to. My husband told me twelve years ago, when we were first dating, that he loved me no matter what but liked my appearance best when I wasn’t wearing makeup. Since both he and I have the same preference, I only rarely wear any.

      Thank you, Byron, for not making me feel like I’m automatically failing to look appropriate by not wearing makeup. I do make sure to wear sunscreen every day, however, particularly important as I have very fair skin.

      1. Amanda, I also wear little to no makeup on a day-to-day basis — maybe some tinted lip balm or a neutral lipstick. I wear eye makeup only for special events, and I never wear blush or foundation. Many women at my local country club do look more made up, however. I think it’s up to the woman to decide how much or how little makeup she is comfortable wearing. The liberating part of the “old money” lifestyle is knowing you have nothing to prove to anyone else.

  5. Hello Byron,

    Further to your reply to K.Lee :

    I do not think it is whether the rules still apply, nor who one might bump into.

    It is simply what one does.


  6. Sporting an olive sports jacket, khaki pants, brown monkstrap loafers and navy socks with more or less matching belt, tattersall buttondown collar shirt and maroon knit tie here today. While Zoom’ing for work from home AND taking The Young Master to a dentist appointment later. All well-broken in, tried and true pieces that work in various permutations with other items as part of various spring, summer, and early fall ensembles. It is so easy tossing on the classics without much thought or effort. The oft heard claim that it somehow takes too much time to dress presentably makes no sense to me.

    Best Regards,


    1. Sounds very dashing Heinz, and I agree with you about dressing presentably. I’m suffering some side effects from the Coronavirus vaccine which brings out the nitpicker in me. That’s probably why I feel compelled to point out that you mean combinations, not permutations. Sorry for being a noodge. I’m sure I’ll be feeling better soon.

  7. I will put forward Nordstrom as a great place to look for OMGal items, including shoes. They have superior ways to search items online, and a great variety, also showing “looks” that I really like to see to plan outfits. Most of all, I appreciate their customer service policies, and everyone I have communicated with at the stores or online have ideal manners. I don’t really go in for OMGal items listed since I prefer more feminine looks, but I understand the spirit!

  8. Pick Clothing out with caution.

    A number of retailers are now selling clothing with elastic waists. Capitalizing on the fact people are working from home with the need to be “comfy”. Don’fall victim to this. Elastic waist pants are not only not old money, but bad for your health. You will not feel yourself gain weight before it’s too late. The exception to this is the morning workout clothing (in my case the early morning walk). Consider Hanes for your workout attire. You can get a multi pack of heather grey work out t-shirts and several sweat type pants for about $40.00, then you are done and can ignore advertising for “comfy” clothes. As I noted before I am careful of No Iron cotton which are chemically treated clothes. Lands End Hyde Park oxford shirts are a great value and seem to last forever. Though I have not tried them out, but Orvis sells Khaki’s called the Ultimate Khaki (the kind Grandpa wore) they are 100% natural fabric. (Ever since I learned how to sew a tear or a hole in pants I tend not to purchase as often, it may be a while before I splurge on a purchase).

  9. Hello, may I please ask the fashionable ladies reading this blog for their recommendations for summer sandals and shoes in general? For example, is the women’s Gucci horsebit loafer a shoe that one would invest in, or is that considered indiscreet? Thank you for your suggestions.

    1. Hi Renee, My apologies for the slow approval process. I’m sure Amy and some of our OMGs will have some suggestions. I’m okay wiht the Gucci loafers. They just get better with age, IMHO. Opinions, anyone else? Thanks, Renee. – BGT

    2. I think most OMGs would say that horse bits belong on horses, not shoes. But Gucci makes high quality shoes that look good and I certainly would not call them indiscreet.

    3. I’m a few months late to this. Gucci loafers are appropriate as long as you get them in black or brown leather. Ideally, you could try to find vintage Gucci loafers in good condition — in my opinion, vintage is almost always better. Sperry also makes great penny loafers, and it’s hard to go wrong with their boat shoes as well. For sandals, try Jack Rogers.

  10. To follow on from Kathie’s comment, for women who need to look polished, I would suggest going to a reputable makeup counter at a good department store. Do not be seduced by the flashy (hello MAC, Charlotte Tilbury etc). I suggest Bobbi Brown as a good start. Even though the founder is no longer with the company, the natural no-makeup look has been the signature from the beginning. It is easy to look polished and natural with a few products and some technique. The products are incredible. The Duchess of Cambridge used a Bobbi Brown makeup artist prior to her big day 10 years ago, and did her own makeup on the day. She continues to use the same basic products and look, but toned down for everyday events.

    House of Bruar is an excellent source for women’s classic clothing. It has a wide range of sizes and clothing that is well made and stands the test of time. I have bought shoes and boots that were made in Spain and are so well made and comfortable. The women’s shirts are classic and are 100% cotton – no spandex, feminine fit, iron-free labels thankfully. The VAT that you do not have to pay can go on shipping. Their return policy is very good and they stock reliable brands.

    As we continue to work from home, and are fortunate to be able to accommodate Zoom meetings and walking the dogs in daylight hours, I think that it behoves us to dress well for ourselves, regardless of what others are wearing. No graphic/band tee shirts, no elastic-waisted pants; wear proper shoes and socks and commit to good grooming. If you use your hands when emphasizing a point, make sure that your nail polish is not chipped.

    The Duchess of Cambridge provides very helpful examples of what can be worn for “dressed down” days that are classic and appropriate. Her visits to outdoor and scout events throughout the Commonwealth give multi-seasonal ideas. The Princess Royal is also a good example. Both are frugal and wear the same items over and over. You can never go wrong with cotton, wool, tweed and silk.

    Renee, I’m not sure what sandals you need for which occasions. A broken foot and surgery a few years ago has kept me in Dankso and Naot sandals. Loafers are classic, whether they are Gucci or a less expensive brand. Open-backed sandals are not a particularly good choice as the shoes tend to clack on flooring more than ordinary sandals, and few people have mastered the art of walking in them without having to scrunch their toes. Nordsrom has a wide variety of sandals, and again House of Bruar is also a good choice. I hope that helps.

  11. I now mostly accessorize my ivy/old money style wardrobe with ties and pocket squares from Turnbull & Asser.

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