Speaking as a staunch advocate of modern-meets-classic style (it’s kind of, like, my whole entire deal), I tend to advocate avoiding trends in favor of timeless looks.
But one recent trend I’m actually thrilled about is the rise of so-called “old money style,” because in some ways, it’s actually kind of an anti-trend.
Rather than being obsessed with what’s new and now, the old money look embodies a refined aesthetic that’s deeply rooted in tradition, sophistication, and the kind of quiet luxury that’s classy, but never showy.
Unlike the flashy (and in a lot of cases, garish and over-the-top) fads often seen in contemporary fashion, the old money look is understated, focusing on quality craftsmanship, timeless pieces, and a color palette that lends it a subtle but unmistakable air of elegance.
It owes its origins to the effortless style of aristocrats (hence the name), who were comfortable in their wealth, and therefore didn’t feel the need to show it off with their style.
Instead, their clothing was more about understated elegance and timeless charm than about keeping up with fast-changing trends.
Why The “Old Money” Look (Somewhat Ironically) Works So Well in the Modern World
In the age of TikTok, Snapchat, and whatever social media platform has already supplanted those two since I started writing this sentence, fads come and go at a dizzying pace.
By contrast, the old money aesthetic offers a respite.
[image: Hockerty]
Rather than spinning yourself in circles in a desperate attempt to keep up with the latest trend, the old money look gives you a chance to get off the ride entirely, and focus on the kind of timeless style that always looks great, no matter what the latest influencer of the day is wearing.
Plus, in the sea of fast fashion that most of us find ourselves swimming in nowadays, opting for the old money look is a powerful way to stand out and separate yourself from the pack.
How to Dress “Old Money” for Men
From the core tenets of the old money aesthetic to the must-have wardrobe essentials and accessories, the comprehensive guide below will walk you through (damn near) everything you need to know to master old-money style.
Whether you’re dressing for formal occasions or casual outings, my goal is to show you how to build – and, crucially, wear – a wardrobe that takes full advantage of the old-money look’s timeless elegance and sophistication.
What is Old Money Style?
Old Money style refers to the fashion and lifestyle associated with families who have what some would call “generational wealth,” and others might (more profanely, but I would argue more accurately) call “f*ck you money.”
Basically, the Old Money aesthetic evokes the kind of understated elegance, effortless sophistication and never-goes-out-of-style timelessness associated with the sort of families who have trust funds, private club memberships, and their names on buildings.
[image: The Tie Bar]
(Think families like Vanderbilt, Rockefeller, Carnegie and Kennedy, and you’ll be on the right track.)
Of course, whether or not people who come from this kind of heritage actually have effortless sophistication, grace and style is highly debatable.
But nonetheless, the old money aesthetic stands as a sort of Platonic ideal that’s worth striving for—and the good news is, you don’t actually need much money to make it work.
Key Principles of Old Money Outfits for Men
So, what if you don’t come from a family whose name is on a building at Harvard, but you want to dress like you do?
Well, I’ve got news for you that’s as good as it is ironic:
You don’t actually need a ton of money to nail Old Money style. You just need to be aware of the foundational principles that the style encompasses, and find clothes that fit the bill.
Here are a few elements to keep in mind if you want to adopt the Old Money aesthetic for yourself:
Timelessness
[image: Banana Republic]
Timeless elegance is the essence of old money style, and arguably its most appealing aspect.
When your grooming game leans toward classic styles and your wardrobe consists of pieces that have remained stylish for decades, you don’t have to worry about what’s trending, because you know that what you’re wearing will always look polished and sophisticated.
Staples like navy blue blazers, well-fitted polo shirts, wool tweed jackets, or a good pair of khaki chinos are all good examples of core pieces that basically never go out of style.
The Old Money aesthetic evokes the kind of understated elegance & Timeless style associated with families who have their names on buildings
Quality Over Quantity
In addition to its timeless aesthetic, one big reason why the old money look works so well is its emphasis on quality over quantity.
Instead of filling your wardrobe with dozens of cheap pieces that correspond with various fads, focus on acquiring a few high-quality pieces that will stand the test of time.
A well-made and custom-tailored suit, a handcrafted pair of leather loafers, and a classic white dress shirt are more valuable than a closet full of trendy items that will fall out of favor by this time next year.
Subtlety
Both the images above feature Gucci shirts. But one is great, and other is… grating, to say the least.
Defined by its understated elegance, the old money look is synonymous with another “new” trend that I can actually get behind:
Quiet luxury, an aesthetic that upscale luggage brand Carl Friedrik defines as “a resurgent fashion movement that emphasizes investment in high-quality, minimalist pieces that have timeless appeal.”
And “quiet” really is the operative word here.
Properly embodying an old money aesthetic means evoking the classic look of stylish figures like Jay Gatsby and Don Draper (two characters who didn’t come from old money, but dressed like they did), without the garishness and trying-too-hard desperation that comes from sporting designer labels.
Or, in the case of Cousin Greg’s erstwhile date, a designer pattern…
Avoid flashy logos, bold patterns, or overly trendy garments like the plague. Instead, opt for subtle, classic colors like charcoal gray, navy blue, beige, and cream.
These shades convey sophistication and offer enough versatility to be worn in various settings.
Fit and Tailoring
When you’re trying to pull off the old money look, proper tailoring is essential.
[image: Charles Tyrwhitt]
It doesn’t matter how expensive, high-quality or luxurious your clothes are:
If they don’t fit, they’ll look like shit.
Make sure that your suits, dress shirts, and trousers are well-fitted to your body, emphasizing your natural lines without being too tight or too loose.
Essential Wardrobe Pieces for the Old Money Aesthetic
OK, so now that we’ve gotten both the essential old-money characteristics and hilarious Tom Wambsgans memes out of the way, next let’s take a look at the core old money wardrobe pieces you need to have in order to start building out the look.
Suits and Blazers
Classic Navy or Gray Suit:
A navy or gray suit is a must-have in any old money wardrobe.
Both colors are as timeless as they are versatile, and suitable for everything from business settings to formal events like weddings.
As alluded to above, with suits your best bet is to look for high-quality fabrics that will last for years. (But the good news is that you don’t have to break the bank in order to find them.)
Blazers and Sport Coats:
Following the same logic, a tailored blazer in a neutral color is another key piece—especially since so few of us wear suits on a regular basis anymore.
A well-made and well-cut blazer is one of the most versatile pieces a man can own. It can be dressed up with dress pants and a white dress shirt, or dressed down with jeans and a tee for a smart-casual look.
Pretty much any store that sells suits will also sell blazers, so they’re not hard to find. But with blazers in particular, I recommend opting for one in a stretch fabric.
It might give the jacket a slightly more casual look, but it makes it a lot more comfortable, not to mention easy to travel with.
Shirts
Crisp White and Light Blue Dress Shirts:
The foundation of any old money outfit, a well-fitted dress shirt in white or light blue is basically mandatory.
These colors are versatile and can be paired with almost any suit, blazer, or trousers, so you’ll find that you reach them for more than just about any other piece in your wardrobe.
Oxford Cloth Button-Down (OCBD):
Another staple of old money style, the OCBD is to dress shirts what blazers are to suits: slightly more casual but infinitely more versatile.
And for most of us, that makes them even more essential.
As their name implies, button downs have a button on the collar that helps keep the collar in place.
When New York Magazine’s Strategist blog interviewed me a few years back for an OCBD roundup they were doing, I recommended Bonobos’s stretch Oxford, and I still stand by that suggestion.
It’s perfectly cut, comes in a ton of great colors, and offers a wide range of both lengths and fits, so it’s pretty easy to find one that will nicely complement your frame.
Pants
Tailored Chinos and Wool Trousers:
Well-fitted chinos are hands-down the preferred casual pant style of the old money set, who tend to wear them in classic neutral colors like khaki and navy.
Another )slightly dressier but no less versatile) option is a pair of wool trousers in grey or charcoal, both of which offer a great blend of warmth and sophistication.
Old Money Advice: Forego Trendy Fits
And in keeping with the timeless spirit of the old money look, avoid overly trendy fits.
Throughout the 2010s, that meant super-tight skinny pants that practically looked like they were painted on.
In the 2020s, the pendulum has swung the other way, and today a ton of brands are selling wide-legged models that look like they belong on the mast of a sailboat, not the legs of a modern gentleman.
Your best bet? Split the difference and opt for a pant leg that’s slim, but not skinny.
Knitwear
Cashmere and Merino Wool Sweaters:
One of the best ways to maintain the old money look when it’s time to layer up is to invest in high-quality sweaters made from cashmere or merino wool.
Classic sweater styles like v-necks, crewnecks, shawl collars and cardigans are all good choices for the old money look.
As you’ve probably gathered by now, your best bet is to opt for similarly classic colors like black, navy, gray, and camel, which are perfect for layering over shirts and under blazers.
But you can also experiment a bit here. Slightly less common sweater colors like olive green, burgundy and tan all fall squarely in the “old money” category, but are distinct enough to help you stand out from the commonly colored crowd.
Footwear
Leather Loafers and Oxfords:
High-quality leather dress shoes are non-negotiable. (Which, come to think of it, is a good rule for both the old money look and for life.)
A pair of well-maintained Oxfords or loafers in black or brown can elevate any outfit, adding a touch of refinement and class.
Boots for Casual Settings:
For a more casual yet still sophisticated look, opt for a chukka with a refined toe shape or Chelsea boots in suede or polished leather.
Both styles are are perfect for pairing with jeans or chinos.
Outerwear
Trench Coats and Overcoats:
A classic trench coat or overcoat is an easy way to evoke the old money vibe, and a versatile piece that you can wear for years with relatively little maintenance or upkeep.
Of the two, a proper trench coat is decidedly more old-school. It evokes classic gentlemen of the black-and-white era, like Cary Grant and Humphrey Bogart, and still looks like a million bucks today.
But if you’re a little self-conscious or worried that a full trench might look more like Inspector Gadget cosplay than sharp 21st-century style (which, fair), then a topcoat or overcoat is the way to go.
It’s just as classic as a trench, but tends to be more commonly worn today, making it a safe choice that’s still undeniably stylish, and well within the old-money paradigm.
Barbour Jackets:
A nod to the old money country aesthetic, Barbour jackets are practical and stylish. Made from waxed cotton, they offer both durability and a timeless look.
You see Barbour jackets a lot if you are forced by your wife or girlfriend to watch that show The Crown, about the British royal family.
But the best example of both their old-money credentials and general bad-assery was in Skyfall, where Daniel Craig’s 007 wore one to fight off bad guys in the Scottish Highlands.
Nailing the Details:
Old Money Accessories to Further Elevate The Look
Now that we’ve covered Old Money’s most essential principles and pieces, let’s talk accessories.
Some guys think of accessories as finishing touches that don’t matter as much as core pieces like shirts, shoes and jackets—but that’s a big mistake.
If you pair Old Money clothes with the kind of shitty wrap-around sunglasses that Dwight Schrute used to wear, I promise: it’s not going to work.
To help you avoid that fate, here are a few pointers on what to look for in common accessories that will complement and elevate your old money attire.
Watches
Classic, Minimalist Timepieces:
A nice watch is a core Old Money accessories because it encapsulates so much about the aesthetic.
In a world where everyone carries at least one (and often multiple) digital devices that tell time perfectly, watches are much more about fashion than function.
Opt for a minimalist design with a leather strap and a simple, elegant face, like Bulova model pictured above. Avoid overly large or flashy watches—remember, with the Old Money look, subtlety is key.
Belts
Leather Belts in Classic Shades:
Invest in a high-quality leather belt like this one in a versatile color like black, brown, or tan. A well-made leather belt is a small detail that adds a lot of polish to your ensemble.
But remember—the same style rule that applies to any look applies here:
Your belt should match your shoes – or at least be in the same general family – for a cohesive look.
That means brown shoes go with a brown belt, while black goes with black, etc.
It’s also usually a good idea to apply the same rule to your belt’s material.
If you’re wearing suede brown shoes, a brown leather belt in the same color family is fine, but a suede belt in a matching color is finely tuned.
Ties and Pocket Squares
Silk Ties in Solid Colors or Classic Patterns:
If you’re wearing a tie, silk is a classic, elegant option that evokes Old Money without being too showy.
A silk tie in a solid color or a subtle pattern, like stripes or dots, can add a subtle touch of sophistication.
The safe move is to choose ties in classic colors like navy, burgundy, or dark green, but ties are one area where it’s easy to have a little fun, too.
Don’t be afraid to try ties in brighter colors that you wouldn’t wear in any other context.
Pink, yellow, orange and light green can all work well when paired with complementary suit and shirt colors.
Pocket Squares:
A pocket square is a great way to add a pop of color or texture to your outfit without being flashy.
The best move here is to choose your tie color first, then pick a pocket square that either matches or complements it.
Eyewear
Timeless Frames:
Eyewear fads tend to come and go pretty quickly.
One minute, big, chunky square frames are the must-have style, and the next it’s thin, round, wire frames that are so subtle they’re barely there.
But, as with other aspects of fashion, one big advantage of the Old Money trend is that it allows to get off the “new and now” carousel.
Instead of worrying about what’s hot right now, opt for a tried, tested and true style that looked great 60 years ago, looks just as sharp today, and in all likelihood will continue looking dapper for decades to come.
If you’re looking for sunglasses, opt for the kind of classic shades that well dressed men have been wearing for decades.
A lot of those frames work just as well for eyeglasses, but for maximum effect, make sure to choose the right frame style for your face shape.
Hats
Flat Caps and Fedoras are Your Friends
If you’ve read this far (thanks for hanging in there, by the way), you probably won’t be surprised to learn that the best old money hats for men are ones that were actually fairly commonplace 60 or 70 years ago.
Hats like fedoras, flat caps and school boy hats all have a sophisticated, old-school vibe that’s perfect for the old money look.
Choose one made from wool or tweed for colder months, or a lightweight cotton version for summer.
But be warned:
Pulling off an old school hat in the modern age can be a tricky balancing act. Which reminds me, I should probably issue a warning…
And Finally, a Word of Warning:
Be Careful Not to Cosplay
(It’s easier than you’d think—and looks dumber than you’d hope)
As mentioned above, the main reason I like the “Old Money” look is that it evokes the classic gentlemen of yesteryear, and harkening back to a time when fedoras and trench coats were commonplace.
But be warned: there’s a (pretty big) problem with leaning too far into the Old Money aesthetic.
When you ignore modernity completely and dress like an extra from the set of The Great Gatsby or The Talented Mr. Ripley, you run the significant risk of looking more like a stodgy old grandpa than a put-together modern man.
That’s why I prefer to split the difference between today’s trends and yesterday’s classics.
Check out the Modern-Meets-Classic Manifesto to find out how to merge the style, sophistication and social grace of a classic gentleman with the technology, tastes and expectations of the 21st century.
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Photos (L to R): Proper Cloth, The Tie Bar, Proper Cloth
Illustration: Irreverent Gent
