Old Money Aesthetic: Sometimes Musty, Always Relevant

Old money men’s style is trending among the young and the new. Why? And what is it truly? It’s not always exactly like the reels you see on social media. Let me elucidate.

A few years ago, the old money aesthetic burst onto social media. At one point, it had something like close to three billion views. 

It’s actually quite evergreen. And I, your humble TMM writer, have covered this phenomenon several times. I don’t mean to sound completely wretched, so bear with me. I have brilliant primary resources on the topic.

I’ve seen this old world set and continue to see them in their natural habitats. I saw them every year when my parents, both Yale legacies, took me to The Game. I watched them fundraise when my mother brought me as her companion and assistant to Connecticut DAR charity events. 

Even today, I work for a 280-year-old auction house that formerly had the Duke of Devonshire on the board. (He’s a good guy, by the way. He hails his taxis.)

And beyond all of that, my Eton-graduate father and Yankee mother were forced to relocate to Beverly Hills when I was young. I’ve seen a new money style, too. I have the control group and the treatment group.

Today, we’re going to explore old money men’s styles. What it actually is. What social media thinks it is, whether one or the other, is more important to your personal style. And the fact that within a culture of people, not everyone dresses the same.

What Is Old Money Exactly?

Old money styling is simple, elegant, traditional, and understated and implies a certain lifestyle. This is the case in both design and fashion. Craft and practicality take precedence over trends.

So what is this “certain lifestyle” I speak of? Well, it begs the question: What is old money?

Source: Wikimedia

Technically, it refers to people who inherit wealth instead of, or in addition to, generating it themselves. Still, the “aesthetic” making its rounds in social media and fashion magazines, leans toward the oldest old money. 

Think the Cavendish family over Hollywood nepo babies.

It pulls from perceptions of the landed aristocracy in England or prominent Mayflower descendants in East Coast America. Boston Brahmins and New York Knickerbockers are examples of the latter.

What Is Old Money Aesthetic? What an Outfit Must Imply

Essentially, it’s a set of uniforms worn without fear of being seen in the same look over and over again. Moreover, old money is rarely as rich as new money. My grandmother used to say, “Richard Branson is, after all, richer than the Queen.”

It’s highly aware of dress codes, though there are “proper” ways to break the rules, too. These agreed-upon broken rules are a sort of secret language the old world set has among each other.

Notice how the Prince of Wales doesn’t always wear a cummerbund with his tuxedo. Or see how James Matthews wore a sports watch to his wedding?

New money simply implies richness, which means expensive things. Old money implies a specific way people work and play.

Places associated with this set include old social clubs (Somerset Club, not SoHo House). Other institutions include the Ivy League, Oxbridge, and the ancient universities, as well as old Protestant (mainline only) boarding schools and prep schools.

The Isles of Scilly or Nantucket are popular places to holiday.

Source: Labour Union

Associated activities include hunting, paddle sports, boating, rugby, equestrianism, and art collecting. Other habits include a daily happy hour (a whiskey neat over some mixologist’s concoction or, God forbid, something non-alcoholic) and exotic travel.

So when it comes to style, a $70 Eton College sweatshirt boasts more social capital than a $3,000 Louis Vuitton cashmere scarf. Cheap boat shoes achieve old money implications more effectively than Common Project Achilles does.

Let’s get into some specifics.

Old Money Fashion

Here are some essentials. Then, we’ll move on to some of the sartorial mores. Notice how you can find a connection between all of the pieces with the above activities and memberships.

Old Money Casual Clothes

  • Cable-knit anything
  • Cardigans
  • Knit polo shirts
  • Pique polo shirts
  • Khakis
  • Rugby shirts
  • Madras shorts
  • Red chinos, aka “Nantucket Reds”
  • Linen pants
  • Linen button-ups
  • Turtlenecks
  • Seersucker pieces
Aran Sweaters featuredAran Sweaters featured

I’m not saying that they don’t wear crew neck t-shirts or baseball caps. However, those pieces don’t imply any lifestyle. That is unless you’re wearing a Harvard lacrosse baseball cap or a Greenwich Country Club t-shirt.

Old Money Smart Casual Essentials

  • Oxford cotton button-up or button-down shirt 
  • Navy blazers
  • Khakis 
  • Nantucket reds
  • Sweater vest, cable-knit, and cashmere
  • Cashmere sweaters
  • Cardigans
  • White chinos
  • Turtlenecks
  • Tweed sport coats

The smart casual dress code is what I like to call “the nucleus” of the old money style. Both casual and formal dress codes gravitate towards it in a way that other sartorial groups don’t.

More on that later.

Old Money Formal and Professional Essentials

  • Full suit
  • Tuxedo
  • White-tie ensemble 
  • A quality or accessory that casualizes the formal outfit a bit, such as a shawl lapel or forgoing a cummerbund (again, more on that later).

Next, let’s get to some outerwear. Notice the major overlap with the English countryside style? Even if you’re a city boy living on Manhattan’s Upper East Side or Kensington in London, you’ll likely still have a country ancestral estate in Connecticut or Norfolk.

Source: Barbour

Important Old Money Outerwear

  • Norfolk jacket
  • Waxed jacket
  • Safari jacket
  • Quilted jacket with a corduroy collar
  • Quilted vest
  • Gilet vest
  • Tweed vest
  • Rowing blazer
  • Tweed coat
  • Fair isle pullovers and vests
  • Again, cable-knit anything 
  • Relatedly, cashmere anything
  • Trilby cap
  • Deerstalker hat
  • Flat cap
  • Fisherman’s hat/Irish country hat

Old Money Shoes and Accessories

  • Leather or suede loafers
  • Oxfords
  • Dress slippers (like an opera pump)
  • Tapered leather loafer
  • Boat shoes
  • Wellies
  • Riding-style boots (like a chukka)
  • Hunting boots
  • Driving shoes
  • Low-profile white leather sneakers
  • Club ties
  • Pocket squares
  • A proper dress watch
  • A proper sports watch

The Old Money Look

Now that you have the toolbox, here are ways that old money style men put it all together.

“Classic” Fits

Go for classic styles and fits mostly, or better yet, only. This means you should avoid anything overly baggy or overly skinny. I’m talking about slim but not tight fits or regular but not oversized fits. Even within what’s classic, there’s a range.

What you choose may depend on your personal preference, age, or even the season. A slimmer dark trouser in the fall is as appropriate as a looser linen pant in the summer.

I’ve used the different generations of modern royals as an example here before. But, I’ll mention it again because it’s a testament to how old money aesthetic men stick to their guns.

Navy silk duck print tieNavy silk duck print tie

King Charles III wears a higher waist and a looser but clean-lined cut as an elder boomer. That was considered “classic style” when he was growing up. 

The Prince of Wales, an elder millennial, historically wore slimmer suits with a waistline right above his hips. It’s what he and I were told was “classic” when we were growing up.

Now, in the mid-2020s, fashion has come around. Trendy youths now prefer a looser fit and a higher waist. 

Again, old-world style is about sticking to your guns. You’re welcome to follow the pendulum swing ever so slightly, but never give in to the trends in full. At least, not with formal tailoring.

Never Too Casual, Never Too Formal

Remember when I said smart casual is the nucleus? 

See, there’s a misconception that old money men are these wheeling-and-dealing closers. And, sure, there was overlap between the ‘80s Wall Streeters and the Connecticut Ivy-legacy WASPs. 

However, in the old money world, the real flex is understated leisure. That’s why we call them boats and not yachts, no matter how big it is. The word yacht is for the nouveau riche. 

Relatedly, you never talk about the fact of your holiday at St. Bart’s. But, you may mysteriously always have at least a bit of a tan.

In a casual setting, always add structure to your casual outfits. Knit polos instead of T-shirts, for example. Or if you go for a T-shirt, pair it with clean-lined linen pants and maybe a cardigan thrown over your shoulders.

In a professional setting, apply strategic broken rules.

I have a group of friends, all Yale legacies, whose old money grandfathers have known each other since childhood. I remember seeing a photo of them, with their work colleagues, having martinis at 21 Club.

You can tell our grandfathers apart because every other man was in a full three-piece suit and tie. The old money men, however, wore v-neck cable-knit sweater vests instead of proper suit vests.

Another way to casualize a full suit is to wear a club tie instead of a solid one. Another easy switch is to wear leather loafers instead of lace-ups.

And when in doubt, go for the ultimate preppy uniform: The broken suit. And the ultimate form of this? A navy blazer with gold buttons, club tie, and khakis. I saw this outfit up and down the Harvard campus, on teaching fellows, and during Final Club initiations. 

For the most formal situations, the old world set already cleverly incorporated casual qualities into the white tie and black tie worlds.

Ever notice how a shawl collar cardigan looks suspiciously like a smoking jacket you’d wear at home? And yet, it’s suitable for a tuxedo collar. I can say the same thing about dress slippers and opera pumps.

But, to really get on the inside, here are more ways to break sartorial rules quietly.

Proper Rule Breaking

First off, all of the casualization mentioned above was once rule-breaking. Why wear a sporty sweater vest with your suit?

Another way to “properly” break a rule is by wearing a sports watch with your tuxedo. Faux pas? Yes. Unless the watch is a family heirloom. In which case, you’re just signaling to the other old-money people in the room that you might be one of them.

Family heirlooms are always allowed in formal settings, within reason. So, no, this doesn’t include your dad’s vintage Nikes. Think more along the lines of watches, men’s jewelry, cufflinks, no matter how worn out, or a lapel pin.

When James Bond first paired his Submariner with a dinner jacket in Dr. No, sartorial traditionalists thought it unbecoming. The old money set saw it as a wink and a nod. 

Seasonal Colors and Fabrics

It’s highly important to dress for the season. Think brighter, looser clothes in the summer, lighter clothes (especially pastels) in the spring, and darker, more structured pieces in the cold season.

Remember, this breed is a practical set.

This is important even if you live in a seasonless place, say, LA.

How one dresses is inextricably related to the social calendar, which must always be honored. Grouse season is in the fall, as is New York Fashion Week.

Cotillion season is in late winter or summer, depending on whether you’re an Upper East Sider, Londoner, or Charleston gentleman. Auction season is in November and May.

And so on.

Regardless of the season, soft, neutral colors like beige and tan are often your foundation. Pops of color must be meaningful: Princeton orange or Nantucket reds, for example.

Old Money Outfits

Straight from the internet machine, here are some outfits that emulate everything I just told you.

The Preppy Uniform

Source: @typicallytrad

Sporty Leisure

Source: @bestofbritishstyle

Shawl Collars and Strategic Rule-Breaking

Source: @karltonmikotyack

Casual and Loose but Structured

Source: @oldmoneyculture

Loose Linens for Summer

Source: @bestofbritishstyle

Conclusion: Incorporating the Aesthetic Authentically

When it comes to old money aesthetics, anyone can incorporate a lot of the timeless elegance imbued into the look.

Perhaps you love a tweed jacket, but as a trendier person, decide to wear a boxier fit. 

Even if you find many of the tenets boring, going for practical, well-made pieces benefits anyone’s closet. And this is despite your personal style.

Oh, and don’t wear a Princeton pullover unless you went there (legacies, however, are allowed).

Questions? Comments? Sound off!

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