Nowadays fads come and go faster than ever, especially in the age of TikTok, Instagram and whatever social media platform has already rendered those two obsolete since I started writing this.
(Case in point: in the time between when I first started working on this article and the time I hit “publish,” TikTok was deemed illegal, banned, and then kinda-sorta reinstated. Honestly, it’s the Wild West out there.)
That’s why the Old Money look is such an appreciated change of pace.
Nowadays a number of brands offer the sorts of classic styles that eschew fads and trends in favor of sophisticated, rakish and (this part is crucial) timeless looks that never go out of style.
But while building a classic capsule wardrobe is a great way to stand out in style, if you’re only doing Old Money with your clothes, you’re missing out on a golden opportunity.
Whether you want to project more professionalism or elevate your everyday style, a good Old Money haircut can help take your overall look from “good” to “Good God—that’s a handsome man.”
Below I’ll break down the haircuts that best capture the classic look of Old Money style, and provide a few tips for helping you achieve a poised, polished and enduring look.
The Classic Side-Part
What Makes it Old Money:
The epitome of refined elegance, the classic side part refers to a sharply defined, sleek cut that bridges the gap between traditional sophistication and modern style.
It’s associated with characters like Don Draper and his real-life equivalents, which projects both confidence and executive-level energy.
How to Get the Look:
With a side part you can either go for a slicked-down look, like Don Draper, or a looser and dryer style, like Jon Hamm often wears in real life.
In both cases your best bet is a good pomade. If you’re going full Draper, apply about a finger tip’s worth of product to wet hair and comb through thoroughly.
If you’re going for the Hamm look, dry your hair thoroughly before applying and use about half as much product.
The Ivy League Cut
What Makes it Old Money:
The Ivy League may actually be the ultimate Old Money haircut.
A short look that strikes a nice balance between intellectual charm and effortless style, it’s less formal than a full side part, but still gives you a smart, professional look that conveys casual sophistication.
How to Get the Look:
With an Ivy League you’ll trim the sides down a bit shorter than you would with a Classic Side Part, but leave about the same length on top.
Towel dry your hair then apply a small amount of pomade or clay cream for a look that’s structured, but not slick.
The Tapered Cut
What Makes it Old Money:
A tapered cut is all about clean lines and effortless polish.
The gradual fade keeps things refined without trying too hard, making it a go-to for guys who want a classic, put-together look that nicely straddles the line between classic and modern.
It’s simple, sharp, and quietly sophisticated—exactly the kind of style that never goes out of fashion.
How to Get the Look:
Less is more when it comes to styling. A light touch of product keeps the hair looking natural while letting the cut do the work.
But one word of warning here: it’s kind of high-maintenance.
You have to keep up with regular trims to maintain that crisp, seamless transition, because the look more or less requires you to be freshly groomed.
The Crew Cut
What Makes it Old Money:
Ummm, pretty much everything. The phrase “crew cut” was actually coined to describe the hairstyles of students at Yale, Harvard, and other Ivy League schools who rowed on the crew team, and had to keep their hair short so it wouldn’t blow in their face.
And if there’s anything more “Old Money” than rowing on an Ivy League crew team, I quite literally don’t know what it is.
In addition to being a staple of effortless sophistication, the Crew Cut’s sharp, no-fuss design is also clean, classic, easy to maintain and eternally stylish.
It’s the kind of haircut that never looks out of place—whether you’re on a yacht, at a business meeting, or just out for a casual drink.
Simple, practical, and undeniably polished? Yes, please.
How to Get the Look:
This is another one that requires regular maintenance, because keeping it crisp is key.
Regular trims will maintain its structured shape, while a light touch of styling product keeps things looking natural. (But if you want to really go natural, this is one of the few cuts where you can get away with no product at all.)
This cut thrives on simplicity, so a regular appointment with your barber is pretty much all you need to keep it looking sharp.
The Subtle Comb-Over
What Makes it Old Money:
Not to be confused with the not-so-subtle comb-over that balding guys use to try and hide the fact that they’re losing their hair, the Subtle Comb-Over is a fresh take on a classic comb-over.
It offers just enough volume without feeling overstyled, striking the perfect balance between put-together and relaxed, while giving you a polished, refined look that doesn’t feel forced.
How to Get the Look:
Find a natural part and let your hair fall into place—no need for a stiff, overly sculpted style.
A little bit of product will help keep things controlled while still allowing for movement, but don’t overdo it.
The goal is to look effortlessly well-groomed, not like you spent an hour in front of the mirror.
The Brushed-Up Look
What Makes it Old Money:
The Brushed-Up Look gives you the kind of volume that evokes an effortless movie-star charm—controlled yet relaxed, polished yet natural.
It’s a style that suggests quiet confidence and great taste, without feeling too rigid or overly styled.
How to Get the Look:
Use a lightweight product to guide your hair back while maintaining a natural finish—the last thing you want here is a stiff, crunchy texture.
The Slicked-Back Style
What Makes it Old Money:
Few styles capture old-money sophistication like a well-executed slicked-back look, but be warned: “well-executed” is the operative phrase here.
When done well, this style is bold yet refined, making a statement without trying too hard.
The smooth, polished finish feels straight out of a black-tie event but works just as well in more relaxed settings.
But when done not-so-well, it can make you look less like an old Hollywood movie star, and more like a Philadelphia ne’er do well whose gang is always up to something:
How to Get the Look:
Use a medium-hold gel or pomade for that sleek, glossy finish—but for the love of God, don’t go overboard. The goal is smooth and controlled, not greasy.
Regular trims and a solid hair care routine will keep this style looking sharp and effortlessly put together.
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