When dressing for Fall an Old Money woman isn’t concerned about flaunting her wealth, but rather displaying her taste. She wishes to be well-represented in the world, among her peers, and respects herself enough to invest in quality luxury that will both make her look and feel exceptional. In modern terms Old Money Fall style can be described as a mix of dark academia meets stealth wealth. Slightly brooding, scholarly and introspective, but refined, traditional and effortless at the same time.
Dressing like a woman with Old Money style isn’t about changing one’s clothes or even having money… It’s a manner, an attitude and a lifestyle based on a set of easy-to-follow rules, years of refining her taste, a thorough understanding and appreciation of her own body, and a harmony with her full, rich life.
Since having an abundance of finances usually means access to goods and people not known to the average person her wardrobe will contain brands many have never heard of. A mark of wealth is wearing things not easily identified by someone who is merely familiar with GUCCI or CHANEL. The little-known brands aren’t any more expensive than the popular ones everyone knows about, they’re simply not as flashy, and therefore not on the mainstream radar. However, they’re identifiable by others within the “old money” set as their quality is unparalleled and price point both fair and friendly. An OM woman thinks nothing of spending a small fortune on a life-long staple such as a cashmere and wool winter coat, however she doesn’t choose the coat for it’s impressive price tag, or well-known, “prestigious” label but instead for its usefulness and longevity in her wardrobe.
Remember that, “looking old money” isn’t simply about switching out your clothes for a certain brand. The look also entails clear skin, smooth hair, and an unhurried, gracious attitude.
Before dropping an investment on a new Fall wardrobe consider spending some of your time and resources on refreshing your physical appearance. Switch to a more natural hair color, only ever get very subtle highlights or lowlights. Stay within 1-2 shades of your natural hair color. Discover your skin undertone type and make sure your makeup matches, or better yet, wear less makeup and spend more time on the quality of your skin. Ditch things like glue-on lashes and nails (yes, it’s very obvious when nails are press-on no matter how “natural” the packaging claims them to be!). Consider partaking in a 2 – 4 week Glow Up challenge to transform your appearance and demeanor.
An Old Money woman isn’t concerned with the fashions that come and go each year. She follows steadfast rules when shopping for her Fall wardrobe. These rules vary by woman but they can be ascertained by asking oneself the following questions:
- Is this item flattering to MY body type?
- Could I have worn this item in my 20’s as well as be able to wear it in the future in my 50’s?
- Will the material last and can it be repaired/mended if need be?
Old Money women are less concerned with the price and more concerned with the quality. Remember that a high price point doesn’t equal high quality. An off-the-rack dress can be taken to a tailor with a good understanding of fitting to a woman’s body and turn it into a work of art. No one will care where the dress came from… only that it is of quality material, is appropriate for the occasion, and accentuates your assets while being kind to that which you may want to downplay.
For example, one of the most flattering and high quality dresses I own I discovered in a sad little shack of a vintage shop in South Carolina. After moving to Germany several years ago I took it to a French tailor and received it back looking like a bespoke gown from the House of Chanel itself.
Total cost to me? Less than $200. I’ve had this dress now for 8 years and it looks as good as it did the day it was created. Not a single time goes by when I wear it that women do not ask me where it’s from and men comment how incredible I look. I look forward to bringing it out of it’s box every Fall because it makes me feel most like my absolute best self. The self I always imagined I’d be as a young girl. Fall “fashion” is a feeling, not a specific item.
That being said however, here is my list of must-have wardrobe items I’ve observed most “old money” women possess and (with the proper fit, fabric type and color) look universally flattering and will be useful for most occasions called for by the activities and weather the Fall and Autumn season bring into one’s life every year.
- Cashmere + wool overcoat
- Cashmere + cotton turtleneck sweater (fitted)
- Fisherman’s sweater (preferably from an authentic English mill)
- Coated canvas jacket
- Utility vest
- Raincoat
- Trench coat
- Silk button down blouse
- Raw denim jeans (cut depends on your body type, but high or mid-waisted, slim fit, cigarette and boot cut are most timeless).
- Suede + leather outdoor boot
- Soft leather, to-the-knee, heeled boot
- Leather + suede slip on loafer
- Leather, lined gloves
- Cashmere + wool scarf
- Wool skirt (a-line or pencil, depending on your body type)
- Sheer panty hose in taupe and black
- Mary-Jane style pump with a medium to low heel
- Black, long-sleeve dresses in silk, wool, cotton and knit.
If you have the opportunity to begin building a collection of what will one day become family heirlooms do so with gold jewelry you can enjoy yourself. Heavier gold pieces can be worn during the cooler months of Fall and Winter and something like an elegant, timeless Mido, Tudor or Shinola watch (anywhere between $450 – $2,000 range) is a good place to start. This next viewpoint might be a bit controversial, but after spending my entire life in certain circles I have an understanding of how certain items are currently viewed… While Rolex is lovely (I have a vintage one myself and it’s certainly elegant) they’ve become extremely common. I think the issue is anyone can obtain one now, and many people choose them because they think it makes them look “rich and smart.” However, if you don’t have the bank account and the manners to match, it’s simply boring and over done. Many old money guys and gals will only have a Rolex if it was passed down to them (which is how I have mine) or gifted for a significant event such as a graduation or marriage. Moreover, an expensive piece of jewelry is never something you should purchase on credit or if you have other debt to pay off. Never outspend your income. That is the opposite of true Old Money values. Brand names should never be purchased simply for the logo. If you find yourself craving something affluent ask yourself why you want it so badly? What is the outcome you hope to achieve by purchasing and wearing such a piece?
OM Fall Wardrobe Color Palette:
- Winter White
- Cream
- Black
- Camel
- Tan
- Olive
- Deep chocolate brown
FAVORITE FALL BRANDS OF THE OM WOMAN:
This is a collection of brands based on my personal experience and knowledge from women in my family as well as being lucky enough to be familiar with the closets of many “Old Money style” women, since my childhood, and in my network now as an adult.
- Massimo Dutti
- Ghurka
- Orvis
- Belgain Shoes
- L.L. Bean
- Gerard Darel
- Land’s End
- Shinola (watches)
- Tudor (watches)
- Mido (watches)
- Strathberry
- L.K. Bennett
- Lily Silk
- Barbour
- vintage Ralph Lauren or Purple Label
- Nina Ricci
- Sarah Flint (use link for $50 off)
- Celine
- Smythe
- vintage Burberry
- Aspinal
- Loewe
- Moynat
- Brook’s Brothers
- Delvaux
One way to eventually have the OM style wardrobe of your dreams is to purchase 1 – 2 of the items every season until you’ve accumulated each one. This is both economical and gives you the opportunity to take your time shopping and searching for the perfect piece for you. Keep a list with you of items you already have and ones you’re on the hunt for so that when you stumble upon a vintage shop or opportunity to make an investment purchase you’re aware of your needs and wants and not swayed in the moment.
An instant “trick” to exude the understated, unassuming, easy air of someone who has been used to having money their entire lives is to intentionally NOT purchase your luxury goods NEW.
Here’s an example of how this works: A friend of mine who recently came into a large inheritance (her relatives were quite wealthy, and she possessed a very “old money” last name, grew up with opportunities and a wealthy mindset but her own parents were not financially affluent), was trying to secure a seat on a prestigious art council and wasn’t sure how to go about it. She had all the credentials on paper but didn’t know how to “dress the part,” as the position was a very political one. Instead of flouncing into the interview, wearing all the latest fashions and showing off her newly received wealth she went out and purposefully obtained all the designer things she wanted from luxury resellers, second hand, and ever so slightly “lived in.”
This gave the appearance that she’d had them a long time… which would silently indicate that she must also have had money for a long time.
It’s not about the money… it’s about the air that having money represents: A lifelong enjoyment of the ease and calmness around affluence that having wealth all your life exudes. It was unfortunate that her credentials and personality weren’t enough to secure her the position… But she understood the weight behind how a certain style of dressing carried, and instead of scoffing at the institution, embraced it and used it to her advantage. People who are used to wealth in their lives are typically not garish, easily impressed, rash, attention grabbing or overly talkative. They have manners, know how to use all the different forks on the dinner table, dress and speak intelligently on a variety of subjects, and don’t behave in an unladylike fashion.
Her approach worked and she was accepted onto the council ahead of several other “new money” applicants who dressed in a rather overt fashion.
The point in this story isn’t to encourage you to project a lifestyle that you do not have… but rather encourage you to dress for the job you want and help you understand that (as unfair as it may seem) certain marks command a predetermined level of respect. Don’t hate the game… Learn the rules and be respectful of them.
Looking for Fall fashion tips for men? Check out Byron Tully’s book, Old Money Style, Secrets to Dressing Well for Less, and read his interview with Ivy Style.
