The old-money aesthetic is a style that implies the activities and places that wealthy families are associated with. Think hunting jackets, tennis whites, and boat shoes. Unlike general new money style, it’s less flashy (creams and earth tones), and more about practicality over fashion. Respect for dress codes, seasons, and one’s legacy (family heirlooms, Ivy League patches) are emphasized.
There’s no unobnoxious way to lead with this, but I went to Harvard.
In fact, I went twice.
I did that thing new graduates do to avoid the real world for a few years longer—attend graduate school.
I mention this because that community allowed me to see old-money types in several natural habitats.
On top of that, my WASPy mother is a member of the Connecticut DAR, and I work for a 280-year-old art auction house that, in my time there, had the Duke of Devonshire on our board.
Nice guy, by the way.
When the “old-money aesthetic” started to make its rounds on social media, I was fascinated.
Young people were embracing what they formerly considered musty, while the lens of TikTok served up familiar yet remixed visuals.
I did some in-depth anthropological research on the matter. Meaning, that I talked to friends, co-workers, and connections of all generations from this world. From that, here’s your comprehensive guide on the old-money aesthetic.
What Is the Old-Money Aesthetic?
Sartorially, the old-money aesthetic is a simple, elegant way of dressing and carrying yourself with undertones of an old-money lifestyle. There’s a focus on craft, practicality, and understatedness.
So what is this lifestyle, and how does it translate to clothes? An old-money person, by definition, is someone who inherits wealth instead of generating it themselves.
Still, the style associated with, say, Hollywood nepo’ babies isn’t the same style associated with England’s landed gentry or the New England Brahmins.
To achieve an old-money aesthetic, you want more of the latter. More tradition, less trends.
To further clarify the nuances of the old-world style, let’s compare it to new money fashion.
Old Money vs New-Money Style
The new money style is far more conspicuous.
Yes, my Yale legacy parents can tell you who our ancestor on the Mayflower was. However, I grew up in LA. Beverly Hills, specifically.
Suffice to say, I know a thing or two about new-money style, too.
Critics would refer to new money fashion as flashy and fad-oriented. Admirers would call it bold, cutting-edge, and artistic. It isn’t afraid of mixing things up, nor does it shy away from brand logos.
Old-money style is essentially a set of uniforms, all respectful and highly aware of dress codes. There’s no fear about being seen in the same timeless garments repeatedly.
Keep in mind that the old-money set is typically not as rich as the new money set. As my grandmother used to say, “Richard Branson is, after all, richer than the Queen.”
Moreover, while new-money style simply implies richness, old-money style is specific. It implies what these folks did for work and play and where they did it.
Activities associated with blue bloods include hunting, equestrianism, paddle sports, boating, rugby, art collecting, and uncreative happy hours at old sports clubs (a whiskey neat over some mixologist’s latest innovation).
Places associated with them include the Ivy League, Oxbridge and the ancient universities, old boarding schools and prep schools, old social clubs (Somerset Club, not SoHo house), and places like Nantucket or the Isles of Scilly for holiday.
So when it comes to style, a $50 pullover with the Eton College logo on it has more social currency than a $2,000 Louis Vuitton one with LVs all over it. Going out to brunch? Chukka boots have an equestrian vibe that work boots don’t.
Let’s get into some examples.
Old-Money Outfits Inspiration
Here are some outfits that you can emulate. I’ll also unpack how each embodies tenets of old money.
1. Strategic Rule Breaking and Pops of Color
I want to start with a look that’s fairly surprising, but is embedded with an old-money secret language. Old-world style is usually neutral, understated, and aligned with dress code rules.
So what in the world is this stylish gent doing in red pants? They’re a brighter variation of what could pass as Nantucket Reds, an Ivy League staple.
Some other strategic rule-breaking that’s allowed include wearing shorts with your blazer as long as you’re beach-adjacent (extra points if they’re seersucker or madras) and wearing a sport watch with your tuxedo as long as it’s a family heirloom.
The Prince of Wales does the latter all the time. I’ve been known to do it myself.
When James Bond wore his Submariner with his dinner jacket, style gurus thought it subversive. The old-money set saw it as a wink and a nod.
2. Never Too Fancy, Never Too Casual
When it comes to old-money fashion, smart casual is the nucleus. When you’re casual, you want to be dress smarter than the average guy. When you’re in a suit, you want to add something that implies a sense of leisure.
This is why for decades, WASPy men wore cable-knit vests or even v-neck cricket pullovers with their full suits instead of actual suit vests. In this image, the gent on the right does just that, while both sport club ties instead of overly formal solid ones.
3. Leisure with Old-Money Connotations
So, why is adding a touch of relaxed vibes to fashion so important to this culture? Well, there’s a misconception that the old-money man is some deal-closing banker type. There’s certainly overlap between the two.
However, the ultimate flex is leisure.
The King is a great style icon to turn to, especially when it comes to his casual wear. A high-quality tee, jeans, and bomber combo may imply that you’re stylish and discerning, but nothing more.
Flatcaps, hunting vests, riding boots, and waxed jackets though? They imply that you might be a gentleman farmer who just got back from a grouse hunt at your estate.
4. Always Nautical
Again, always think about the story your outfit is telling. When you’re wearing madras, a fitted pull-over, and boat shoes, it’s saying “I may have just gotten off a boat.”
Dive watches, anchor motifs, and any piece of outerwear made of sailcloth have the same effect.
5. The Intentional Vacation Look
This outfit perfectly achieves the loose yet structured look you want when you’re on holiday. Notice the classic tailoring of the pants, the relatively high waist, and flowy lines. This cut is in style now, but even if it’s not the way you like your suits, it’s perfect for a casual or vacation look.
Meanwhile, earth tones are ubiquitous in British countryside style, which heavily overlaps with the old-money aesthetic.
And of course, he adds even more soft structure with a safari jacket. The blue bloods of the world love their safari trips.
6. The Ultimate Preppy Uniform
We don’t have a big frat scene at Harvard, but we do have something called Final Clubs. During the sorting events (called punch events), I saw a lot of navy blazers and khakis. Then when I went back to grad school, these same boys who were now teaching fellows made it their go-to work outfit.
It’s what I call the ultimate preppy uniform. When in doubt, throw this on and you’ll look the part.
I love how this guy adds a small pop of Princeton orange via a pocket square. It goes to show you can express yourself even within this uniform-centric culture.
7. Quiet Luxury
I already referenced the importance of sweater vests. This outfit perfectly illustrates that. It adds a touch of structure to an otherwise extra loose outfit.
It makes it so that the lack of tailoring doesn’t go against him. Think of this as the old-money equivalent of leaving the house in sweatpants. Just a ten-minute errand to grab a coffee, perhaps.
And remember, beige and cream aren’t boring. They’re classic.
8. Town and Country
Incorporating sporty country aesthetics in an urban outfit is a great way to visually tell your old-money story. This guy is me, by the way.
Sure, a cricket sweater and a quilted hunting jacket are classic New England staples, individually. But why am I wearing them together? Who cares? I’m in Manhattan, not on the actual cricket field or the hunting grounds.
The point is they’re weather-appropriate layers, each connected to a popular New England activity.
Remember when I mentioned that an affordable Eton College sweater is a better way to go than a lavish Louis Vuitton one? It’s because it exhibits your association with a club or lifestyle. The patch on my jacket is from a hunting and conservation association called the Ruffed Grouse Society.
Don’t show off brand labels, but do show off memberships—with tact, of course.
9. The Casual Equestrian
I know riding fashion is more common in women’s everyday style than men’s, but we can get in on it too. I was captain of my high school polo team, so I’m partial to equestrian style.
This riding show shirt paired with white jeans or chinos is an excellent example. And while wearing actual knee-high riding boots may not be most guys’ thing, chukka boots will give off an equestrian vibe appropriate for everyday wear.
10. The Classics Professor
Yes, more cashmere cable-knit. And here’s a tip: Never underestimate the power of a good turtle neck. It adds the structure of a collar and tie but far cozier.
Top it off with an earth-toned suit jacket, and you’ve got a look worthy of any tenured Ivy League professor.
11. A Feast of Textures
While the old-money aesthetic is picky about colors (for the most part), you can go big on textures. Cashmere, tweed and cable-knit all in one outfit? Go for it.
I like this example because it’s a tempered look regardless of everything going on. The main pop is the Fair Isle sweater. The neutral palette of the suit makes the textures blend harmoniously.
Old-Money Style: How to Pull It Together
Color Palette
The foundational palette of old-money aesthetic is rooted in soft neutrals. So think, cream, beige, tan, camel, other light cool browns, grays, slate, and light blues. When you’re choosing a shirt, you 100% have to go for one of these.
In the spring, you can opt for pastels of any color—preppy men in the Hamptons love their salmon shirts, after all. Relatedly, the old world is all about order, so seasonality is paramount (more on this in a moment). This means darker shades in the winter, lighter ones in the summer, and earth tones are important in the fall.
When it comes to outerwear or any layer that goes over your shirt, like a suit jacket or peacoat, you can go for darker versions of the foundational palette. Think navy, charcoal, darker camels, and even olive greens and maroon.
As mentioned, pops of color occasionally make their way in, but they have to be meaningful. The old-money set exudes a quiet pride, so red, white, and blue are common accent colors, as are ones that imply membership to a special tribe: Princeton orange and Oxford blue, for example.
Tailoring Is Key
Your clothes need to fit you well. You can’t go for anything overly baggy or overly skinny. The term “classic tailoring” can range from regular fit with clean lines to slim fit, but not tight or overly cropped.
I’ve already mentioned King Charles III, but modern royals are a good example.
The King, a boomer, wears his suits in a loose but clean-lined cut with a higher waist. Meanwhile, the Prince of Wales, an elder millennial, wears slimmer, less flowy suits with a waistline right above the hips. These are both classic cuts.
And in an instance of a broken clock being right twice a day, Gen Z now prefers King Charles’ suit fits. Old-money aesthetic is all about sticking to your guns.
Shirts
Dress Shirts
Get yourself a crisp, white dress shirt. Maybe two. Dress shirts can be worn in any dress code, including casual ones. You can definitely old-money-ify a jeans outfit by pairing your denim with a white dress shirt instead of a t-shirt.
You’ll also want to opt for dress shirts in several colors from the aforementioned foundational palette. Striped twill and plaid are also acceptable as long as you temper them with clean, solid garments.
And of course, for summers and holidays, you’ll want a loose, but clean-lined linen shirt.
Polos
Polos are a go-to when it comes to casualwear. A pique polo has a country club vibe, while a knit polo has a lighter, more effortless look.
To combine the structure of the former and the lightness of the latter, try a knit polo with cinched hems. This injects some Bond-esque cosmopolitanism into the look.
Pants
Dress Pants
You’ll need dress pants of all types and for every dress code. Like the dress shirt, nothing levels up a casual outfit like wearing dress pants out of context.
Medium-weight wool is a good year-round fabric, while tweed is perfect for fall and early winter. Meanwhile, go for silk blends and linen for the warmer seasons.
Jeans
I know jeans aren’t the first thing that pops into most people’s heads when they think of old-money aesthetics.
However, if you check out the legendary photograph book Take Ivy or simply Google image “JFK Jr casual”, you’ll see some regular-fit blue jeans in the mix.
They’re clean-cut, not slim nor baggy, and they’re styled with loafers, dress shirts, rugby shirts, and the like. Not t-shirts. Not motorcycle jackets.
Black jeans are a bit too cool. The old-money aesthetic isn’t hip.
Chinos
Again, smart casual is the nucleus of old-money style. So of course, chinos are important. You’ll end up wearing sensible khakis most often.
However, forest green chinos have a grouse-hunting connotation, perfect for fall, while Nantucket reds and other faded colors go well with a spring or summer look.
Suits and Outerwear
Remember, tailoring is important. This is especially true when it comes to suits.
The broken suit is an old-money staple, especially the navy blazer with khakis look (or khaki-colored dress pants if the dress code warrants).
Never underestimate how much a suit separate can elevate any casual combination. For example, if you throw a jacket over a polo and chinos, you not only have a practical extra layer in case it gets breezy, but you’ve also added a country club aesthetic to your look.
Feel free to mix it up with single-breasted and double-breasted suit jackets.
And as mentioned, anytime you can add a touch of casual leisure to the suiting, that’ll help nail the old-money vibe. Go for a cable-knit sweater vest or a cashmere cardigan under your suit jacket, loafers over lace-ups, and club ties.
Tweed Suits
Tweed suits are perfect for fall. Professorial aesthetic is a subcategory of old-money style and one way a young prep look can evolve into an adult prep look.
One fun way to style tweed is to pick one with a bright accent weave. If it’s yellow, you can bring it out with some mustard-toned accessories.
Tweed separates are also perfect for practical, casual outfits that provide that gentleman farmer look. A button-down, flat cap, and tweed trousers tucked into wellies, for example.
Think of tweed as old money’s answer to outdoorsy plaid flannel.
Traditional Wool Suits
You don’t actually need a whole closet of different suits. I’d say as long as you’ve invested in one or two good, well-tailored suits, you’re good to go.
Go for navy, charcoal, maroon, dark olive, and even a proper blue.
I wear a full suit to work every day and I only own three: A navy suit, a blue suit, and a gray one with subtle blue accent lines.
Linen Suits
For those business meetings in Palm Beach and Cornwall in the summer, or holidays on Martha’s Vineyard or southern France, linen suits are the answer.
Get them in cream, beige, or white if you want to be extra bold. The only problem with white is that it isn’t as seasonally versatile. It looks chic in the summer though.
If you’re so inclined, feel free to try a looser fit for your summer suits. And don’t be afraid of a little seersucker if you’re at a boat party.
Outerwear
As I mentioned, you want your pieces to be connected to some old-money hobby. This is why there’s so much overlap between British country style and old-money aesthetic. Again, think pheasant hunting and equestrianism.
And even if you’re an urbanite, you’ll want these country staples. Every old-money person on Manhattan’s Upper East Side still has a country estate in Connecticut.
Here’s a list of important outerwear:
- Norfolk jacket
- Quilted jacket with a corduroy collar
- Quilted vest
- Waxed jacket
- Gilet vest
- Tweed vest
- Cardigan
- Rowing blazer
- Tweed coat
- Turtleneck sweater
- Fair Isle pullovers and vests
- Cable-knit anything (vests, cricket sweaters, tennis sweaters)
- Safari jacket
- Deerstalker hat
- Fisherman’s hat/Irish country hat
- Flat cap
- Trilby cap
- Cashmere anything
Shoes
In some ways, you have to be pickier with your casual shoes and boots than you do with your dress shoes.
When it comes to dress shoes, just follow the dress code. With casual shoes, again, pick pieces connected to the lifestyle.
Dress Shoes
- Traditional Oxford lace-up
- Opera pump and other dress slippers
- Tapered leather loafer
Casual Shoes
- Boat shoe
- Wellies
- Chukka boots and other riding boot styles
- Hunting boot
- Brogue
- Loafer
- Driving shoe
Athletic Shoes
- Low-profile white leather sneaker
- Classic tennis shoes (not the performance-forward ones)
- Slip-on sneakers (especially in suede)
Accessories
Accessories are something the old-money set isn’t afraid to go a bit flashy with.
Don’t get me wrong. They’re not running around with 50-millimeter Hublots. But, the men aren’t afraid of the Pateks and Rolexes of the world. Meanwhile, the ladies certainly don’t sneeze at diamonds and pearls.
Watches
As long as you have one sport watch and one dress watch, you’re good to go. Remember, the old-money folks love a uniform.
That being the case, invest in at least one truly high-quality timepiece.
And if you have a family heirloom, go for that. It exudes pride in your clan.
Jewelry
Men’s jewelry must be subtle. A white gold tennis bracelet here, a small cross necklace there.
To show a level of worldliness, you can even incorporate an exotic piece from your travels. Perhaps on safari you found a rare tribal bracelet.
And finally, if you went to an elite university or boarding school, don’t be shy about wearing your class ring.
Summer vs Winter Choices
Going back to the importance of seasonality, you want to save your breezy linen pieces for summer and your heavy pieces for winter.
I already mentioned this, but go for lighter colors and fabrics in the warm seasons, and darker and heavier ones during the cold seasons. Again, earth tones and tweed are fall staples, while pastels are popular for those warm-weather boat club events, especially in the spring.
You have to honor the order of the social calendar, which is inextricably related to seasons. Debutante balls happen in late winter or summer depending on where you’re from, fashion week and grouse season are in the fall, auction season is in November and May, and so on.
So even if you don’t live in a part of the world with defined seasons, to exude old-money traditions, you dress accordingly.
A navy blazer and khakis are year-rounders.
Old-Money Grooming
For the most part, you want to stick to a clean-cut look. There are some nuances though, but if you want to play it safe, go clean, short, and well-combed—and this includes facial hair.
Hair Style
Short hair is preferable for men, and longer hair should be combed back during the week and at least cleanly styled during the weekend or on vacations.
If you have naturally thin hair, just stick to short hair. The Ivy League cut is a close cut with a side part that became popular among the 1950s “good boys” compared to the rebels who wore pompadours.
If you’re blessed with a thick, JFK-Jr-like mop, never let it get “hippie long.” It shouldn’t go past your ears, and it should never be in your face.
And if you’re balding and it’s visually obvious, do not be ashamed of it. Don’t cover it up with toupees or comb-overs, and just keep the hair you do have short and neat. You’d be surprised at how dignified a man who owns his baldness can look.
Oh, and avoid hair colors that don’t occur in nature.
Beard
The best beard style to go for is a close-to-face full beard.
By full beard, I mean one that goes up to your sideburns and connects to your mustache. Avoid a mustacheless Dutch beard or one that’s disconnected from your head hair and simply circles your mouth.
And by close-to-face, I mean it shouldn’t hide your jawline.
And of course, maintain it by keeping it clean and well-oiled.
Dos and Don’ts for Nailing the Old-Money Aesthetic
| Don’t | Do |
| Go for passing trends and fads, even if it makes you look discerning and cutting-edge | Incorporate meaningful accents and pops of color such as madras, Nantucket red, or Yale blue |
| Wear conspicuous brand logos | Tactfully wear visual nods to associations you’re involved with, perhaps a hat with a Harvard H or a lapel pin from White’s in London |
| Make bright, flashy colors your foundational palette (wearing a neon orange shirt for example) | Anchor your wardrobe in soft neutrals, like beige, cream, gray, and white |
| Wear oversized or extra tight clothes | Stick to classic tailoring |
| “Mix it up” by going for a “rocker look” one day then a “workwear” look another day | Find a uniform for every dress code, the casual ones connecting to old-money activities (boating motifs and tennis whites, for example) |
| Go for big, loud accessories | Wear high-quality investment pieces like Rolex watches, antique cufflinks, or any family heirloom |
| Have fun experimenting with quality items within your budget and finding ways to achieve old-world class through timeless tailoring and neutral palettes while being true to yourself | Have fun experimenting with quality items within your budget and finding ways to achieve old world class through timeless tailoring and neutral palettes while being true to yourself |
Old-Money Brands to Consider
Quality is more important than brand, but the brands below have built their whole aesthetic on old-world style.
British and East Coast American brands tend to lead the pack when it comes to silhouette designs. Meanwhile, you’ll go to specific places and brands for natural specialties, meaning English wool, Italian leather, or Chinese silk.
France also has a long-time influence on elite fashion in the West. Generally, Italian fashion comes from the heart, and French fashion comes from the head. You want more of the latter. Less paisley, more suits.
And finally, new brands like Vineyard Vines and Rowing Blazers are self-aware renditions of preppy style. They’re examples of post-Gossip Girl neo-prep for the younger generations, but they always have great pieces you can incorporate into an old-money wardrobe.
Here are some other staples:
- Bespoke men’s tailors like Turnbull & Asser and Thom Sweeney
- Barbour
- Brooks Brothers
- Hermes
- Drake’s
- N.Peal
- J.Press
- Ralph Lauren
- L.L. Bean
- Sperry
- Kiehl James Patrick
- Burberry
- Chanel
- Dior
- Brunello Cucinelli
Tips for Going Old Money on a Budget
You don’t need to be rich to achieve an old-money look. In fact, the focus on uniformity makes it easier to achieve than a trend-chasing look.
These days, middle-man-cutting brands have made cashmere, good leather, and good suiting more accessible than ever. So if you’re on a budget, look out for these offerings. And you’d be surprised at how much more high-quality a budget suit looks once you’ve gotten it tailored.
Shop at mid-market stores and brands and find clean-lined, structured pieces, in the above-mentioned palette. Department stores are always having sales. So sign up for newsletters from Macy’s or Nordstrom Rack. You just might end up buying a $1,000 Ralph Lauren suit for $300.
Since the old-money aesthetic is all about timelessness, vintage stores are great places to find pieces, especially outerwear.
Moreover, how you wear your pieces makes a big difference.
For example, you might have a Uniqlo button-down and a pullover you got on sale at Banana Republic. Pair that with some leather loafers and pop the sweater over your shoulders and you’ll look country-club-ready at a fast-fashion price.
Relatedly, go ahead and put a cable-knit vest under your suit jacket.
Sure, you should be an Eton alum to wear an Eton pullover. However, you don’t have to own a boat to wear chino shorts with an anchor motif and boat shoes.
You don’t have to have an estate where you hunt to wear a hunting jacket with a corduroy lapel or dress slippers with embroidered pheasants on them.
Look for opportunities to hat-tip to these activities that don’t necessarily imply you participate in them.
Moreover, if you can’t afford a Rolex or Patek, no worries! Just find a practical, non-fashion brand timepiece (or find a vintage one on eBay for $500). Check out Tissot, Longines, and Hamilton.
They all have that old-money hallmark—a strong heritage. Even better, see if you can wear your dad’s watch. Remember, old money is intrinsically linked to family.
Conclusion
Even if you find the old-money aesthetic musty and boring, there are a lot of good takeaways from exploring its tenets.
The focus on quality over quantity allows you to make a pretty minimalist and easy-to-navigate wardrobe.
Similarly, making smart casual the core style allows you to look put-together without looking stuffy on most occasions.
FAQs
Is preppy the same as the old-money aesthetic?
Technically no. However, there’s a segment of preppy style that overlaps with the old-money aesthetic, since old-money people go to prep school. Preppy style as a whole goes beyond that though, with louder, flashier style options. After all, not everyone who goes to prep school is old money.
Will the old-money style trend stay popular?
It will definitely go in and out of style, but its focus on timelessness and quality ensures it’s at least always relevant. No one will look retro when going for an old-money aesthetic.
