The modern Old Money style is a sophisticated fusion of traditional upper-class fashion and contemporary trends.
It draws inspiration from the fashion choices of wealthy, established families while incorporating updated fits and silhouettes to maintain a current appeal.
This style is not just about wearing expensive clothes; it’s about embodying a refined aesthetic that speaks to a heritage of taste and discretion.
Modern Old Money Aesthetic
Modern Old Money is a look that whispers rather than shouts, conveying a sense of inherited taste and quiet confidence.
The style is characterized by a preference for natural fabrics like fine cotton, wool, and cashmere.
The colour palette tends towards classic, subdued tones such as navy, hunter green, burgundy, and shades of beige and brown.
However, don’t be afraid to incorporate occasional pops of brighter colours, especially in accessories or summer wear.
Modern Old Money Style Roots
The roots of the Old Money style date back to the early 20th century’s Ivy League look, a clean-cut way of dressing popular among students of prestigious American universities.
The look emphasized classic garments like oxford shirts, khaki chinos, navy blazers, colourful madras prints, embroidered belts, and boat shoes, creating a more casual yet refined aesthetic.
British aristocratic fashion, including tweed jackets, tailored suits, and country attire, has also played a crucial role in shaping the Old Money style.
Nautical influences such as sailing and the yachting culture of coastal elites introduced elements like brass-buttoned blazers, striped shirts, and deck shoes into the Old Money wardrobe.
The modern iteration of the Old Money style retains these classic influences while incorporating contemporary garments, footwear, accessories, new materials and colours.
It’s about honouring tradition while remaining current—a delicate balance that defines the essence of the Modern Old Money style.
4 Modern Old Money Outfits by Occasion
Putting together a Modern Old Money outfit isn’t about following strict rules but rather about understanding and adapting the principles to your style and lifestyle.
Let’s explore some key outfits that embody this aesthetic for various occasions.
Modern Old Money Casual Outfit
We’ll start with a classic Breton striped long-sleeve t-shirt with horizontal navy and white stripes to evoke a nautical feel while maintaining a timeless appeal.
Pair with neatly pressed Bermuda shorts in a soft, faded red hue—a nod to the iconic “Nantucket Reds” that have been a staple of East Coast summer style for generations.
For footwear, opt for a pair of well-worn leather boat shoes in a rich brown tone.
These shoes should look like they’ve seen many summers on the deck of a yacht, developing a beautiful patina over time.
Complete the look with a navy canvas belt featuring a brass D-ring buckle – a subtle maritime touch.
As the evening cools, you can drape a cream wool or cashmere cable-knit sweater over your shoulders.
Accessorise with tortoiseshell sunglasses in a classic shape—think timeless rather than trendy—and a dive watch with a navy and red striped nylon strap, echoing the colours in your outfit and reinforcing the nautical theme.
Modern Old Money Business Casual Outfit
Begin with a crisp, white Oxford cloth button-down shirt. The fabric should have a subtle texture and a comfortable weight, speaking to its quality.
Ensure the fit is impeccable – neither tight nor loose, with just the right amount of fabric to tuck in neatly.
Pair this with tailored wool trousers in a rich charcoal grey. The wool should have a fine weave with a slight sheen, indicating its high quality. The trousers should break slightly over your shoes, creating a clean line.
We’ll add a single-breasted navy blazer over the shirt. This isn’t just any blazer—it’s a cornerstone of the Old Money wardrobe.
Look for one in high-quality wool with a natural shoulder line and minimal padding. The buttons should be brass, polished to a soft sheen.
The fit is crucial—it should hug your shoulders and nip in slightly at the waist, creating a subtle hourglass silhouette.
For footwear, choose a pair of burgundy penny loafers. The leather should be supple and well-polished, with a patina that suggests years of careful wear. Match these with a belt in the same rich burgundy leather.
Now, let’s add some carefully chosen accessories to elevate the look. Tuck a pocket square into your blazer’s breast pocket – opt for a silk one with a subtle pattern in shades of blue and burgundy, picking up the colours of your outfit. Fold it casually, allowing just a hint of the pattern to peek out.
Wear a classic dress watch with a brown leather strap and Roman numerals dial for that extra touch of traditionalism, and glasses in a timeless tortoiseshell frame.
Modern Old Money Formal Outfit
For formal events, whether a high-profile business meeting or an evening gala, we’ll create a look that exudes timeless elegance and quiet confidence.
The centrepiece of this outfit is a beautifully tailored double-breasted suit in deep navy blue. The wool should be of the highest quality—think Super 120s or even Super 150s—with a subtle sheen that catches the light as you move.
The suit’s cut is crucial. It should fit you like a glove, with high armholes, a suppressed waist, and trousers that fall with a clean break over your shoes.
The lapels should be proportionate to your frame, neither too wide nor too narrow. Underneath, wear a white dress shirt with a moderate spread collar and double cuffs.
The cotton should be so fine it almost shimmers, a hallmark of exceptional quality. Ensure the collar sits perfectly under your suit jacket, with just a quarter-inch of cuff showing at the sleeves.
Now for the tie – choose a silk repp stripe in burgundy and navy. The stripes should be neither too wide nor too narrow, and the silk should have a subtle texture that catches the light. Tie it in a perfect four-in-hand knot, dimpled just so beneath the knot.
For footwear, opt for a pair of black cap-toe oxfords. These should be benchmade shoes with a high shine, the leather developing a mirror-like gleam at the toe. Make sure they’re well-maintained with no scuffs or signs of wear.
Tuck a crisp white linen pocket square in your jacket’s breast pocket and fold it into a simple TV fold, allowing a sliver of white to show above the pocket for a touch of refinement without being showy.
Accessories should be minimal but significant. Choose cufflinks in either gold or silver – family heirlooms if you have them, or simple, classic designs if not.
Your watch for this outfit should be a dress watch, thin enough to slip under your shirt cuff, with a black leather strap to match your shoes.
This outfit isn’t just clothing – it’s armour. It speaks of heritage, sophistication, and a deep understanding of style that goes beyond fleeting trends.
Modern Old Money Style Do’s and Don’ts
When adopting the Modern Old Money aesthetic, most people face similar challenges, such as:
Do
Purchase from Thrift and Vintage Shop
Not everyone inherits a wardrobe of classic pieces or can afford high-end brands. Learn to spot quality items in thrift stores and vintage shops.
Look for natural fabrics, solid construction, and classic designs. With patience and a good eye, you can build a high-quality wardrobe on a budget.
Adapt the Style to Your Climate
The traditional Old Money look is rooted in New England and can be impractical in different climates.
For instance, if you live in a hot, humid area, adapt by choosing lighter fabrics and looser cuts while maintaining the overall aesthetic.
Linen suits and breathable cotton can replace heavy wool while still looking refined.
Customize Off-the-Rack
If you can’t afford bespoke clothing, buy off-the-rack and get items tailored to fit you perfectly.
A modestly priced suit altered to fit you impeccably will look far more expensive and stylish than an ill-fitting designer label.
Don’t
Don’t Sacrifice Comfort
In their attempts to look ‘proper.’, most people make the mistake of wearing uncomfortable clothes.
Avoid shoes that pinch, trousers that are too tight, or jackets that restrict movement. The Old Money look should appear effortless and comfortable.
Don’t Overdo the Preppy Look
It’s easy to fall into the trap of looking like you’re wearing a costume.
Avoid going overboard with stereotypical preppy items like tennis sweaters, boat shoes, and polo shirts simultaneously.
Don’t Neglect Your Body Type
The Old Money style often showcases a specific body type in magazines and media. Don’t force yourself into a look that doesn’t suit your body.
Instead, adapt the principles of the style to flatter your shape. A good tailor can help you achieve this.
Don’t Feel Pressured to Buy Expensive Brands
Some people think they must buy from specific high-end brands to achieve the old-money look. This isn’t true and can lead to financial strain.
Focus on the clothing’s quality, fit, and style rather than the label.
Don’t Forgo Personal Style
While adhering to old-money aesthetics, don’t lose your individuality. If you follow every rule too strictly, you’ll end up looking generic.
Pay attention to sprezzatura and incorporate garments that reflect your personality, whether a unique accessory, a favourite colour, or a modern twist on a classic piece.
Conclusion
As we conclude our journey through the world of Modern Old Money style, remember that this aesthetic is more than just a fashion choice – it’s a lifestyle.
It’s about appreciating quality, respecting tradition, and presenting yourself to the world with quiet confidence and understated elegance.
The Modern Old Money style is not about ostentatious displays of wealth or slavishly following trends.
Instead, it’s about cultivating a timeless wardrobe that reflects your personal taste and respect for craftsmanship. It’s about understanding that true style transcends seasons and fleeting fads.
As you build your Modern Old Money wardrobe, focus on quality over quantity. Invest in well-made pieces that will last in terms of durability and style.
Learn to appreciate the finer details—the hand-stitched buttonhole on a jacket, the supple leather of a well-made shoe, the drape of a perfectly tailored pair of trousers.
Remember that this style extends beyond your closet. It encompasses how you carry yourself, your interests, and your values. It’s about being well-read, well-travelled, and well-mannered.
