When I think “old money,” I think about smoking a great cigar in the library while sipping a well-aged single malt scotch.
It invokes images of great suits and classic, groomed haircuts in an old-school barbershop.
The hallmark of an old money haircut is flow. The sides and back can be almost any length, but the top must be long enough to allow for a bit of flow, which can be styled formally for a dinner party or fundraiser or casually for a day on the boat.
These are my 11 favorite old-money haircuts.
The Basic
This old-money haircut is a timeless classic—not too short or long, but with great versatility and works with most men’s hair types.
For the basic old-money haircut, the hair is left long on top, and the front is long enough to fall below the eyebrow. The sides and back are tapered but with no skin exposure.
For styling, add a dime-sized amount of pomade and comb the hair neatly back with a side part for a more formal look. Conversely, the hair can be swept back loosely with fingers (as shown) for a casual look.
What to ask for: Tell your barber you want a short back and sides, tapered down to a #3 and left long on top. As I always advise, a photo is worth 1,000 words when communicating with your barber.
The Loose Pompadour
The loose pompadour is an excellent choice if you want a taste of that old-money style but still want something short and easy to care for.
This style is faded high and tight on the sides, blending smoothly into the longer top.
I add a bit of pomade for styling and sweep it back with my fingers. It can also be combed and parted for a formal look. With the extra length on top, this cut can also be styled forward and scrunched if you’re in the mood to post a quick TikTok dance video.
What to ask for: A pompadour is a common term widely known by most barbers, so ask for one with a high fade on the sides and back and about three inches on top.
The Layer Cut
Another timeless classic, the layer cut is an excellent option for men who want a bit more length that is versatile and easy to manage.
For the layer cut, the hair is cut using scissors with about five inches on top and tapered a bit around the sides and back.
For variety, the hair can be styled loosely with pomade as shown or neatly parted for a night on the town. On the weekends, just towel dry, throw in a dab of light styling cream, and shake it for a loose, shaggy effect.
What to ask for: Ask your haircutter for a scissor cut, leaving about five inches of length on top with a slight taper at the sides and back.
The Classic Pompadour
The classic pompadour is a haircut that will never go out of style and works well with any occasion or lifestyle.
The hair is tapered close on the sides and back for a pompadour and blended into a longer top.
For this client, I blow-dried the hair up and back to add volume and threw in a bit of pomade for control and shine. Like most old-money haircuts, you can also wear this style loose with bangs hanging over the forehead.
What to ask for: Tell your barber you want a traditional pompadour, making sure to specify how short you want the sides and back and making sure they leave enough length on top to style up and back with a clay or pomade (clay for a matte finish, pomade for shine).
The Classic Taper
The classic taper is another timeless classic and works well for most hair types and face shapes.
An old-school barbershop cut, the classic taper is clipper cut aggressively short on the sides and back and blends perfectly into a longer top, styled back with a high-shine pomade.
What to ask for: A classic taper with three to four inches on top so it may be parted and styled.
The Wolf Cut
The wolf cut is a longer, timeless style suitable for most men and has tons of versatility.
The hair is cut in long layers with scissors with a slight taper on the sides. The back is left a bit longer (think short mullet).
Add a bit of light pomade for styling, and brush the hair back with your fingers. You can also comb the hair back neatly to create a slick-back style.
What to ask for: Ask your barber for a long, layered haircut with the sides cut to the middle of the ear and the back left just long enough to touch the collar of a dress shirt.
The Slick Back
The slick back is essentially the same as a layer cut, with modified styling, and is appropriate for most men with straight to slightly wavy hair. Think Pat Riley back in the day.
For the slick back, the hair is cut in long layers all over the head and then styled straight back with a bit of pomade.
You can also style this loosely, allowing some hair to fall on the forehead for a more casual style.
What to ask for: Ask your barber for a long-layer cut, leaving at least five inches of length on top with a slight taper at the sides and back.
The Comb Over
When I use the term “comb over,” I’m not talking about just combing it over from the side to cover up my bald head cut. I’m talking about a classic taper with a clean and crisp side part.
The comb-over always has enough length on top so the hair can be styled neatly back and to the side. The sides and back can be anything from a bald fade to a longer clipper, but it is always neatly tapered.
What to ask for: A classic taper with three to four inches on top so it may be parted and styled. Tell your barber your preference for length on the sides and back.
The Caesar Cut
People lost their minds when George Clooney first popped up on the television show ER sporting a Caesar. Every woman wanted their man to look like Clooney, so off to the salon they went.
Julius Caesar inspires a Caesar cut. It is cut short on the top and styled forward. A bit of scrunching with a few sprinkles of styling powder will add texture.
The length on the sides and back can be almost anything you’d like if it blends in with the shorter top.
What to ask for: Ask your barber or stylist for a Caesar cut and specify the length you would like the sides and back. For example, “I’d like a Caesar cut about two inches on top and tapered to a #3 on the sides and back.”
The Ivy League
The Ivy League (sometimes called Princeton) was popular among college students and Ivy League universities in the 50’s and 60’s, but it is just as timeless today.
The Ivy League is an excellent option for a guy who wants to capture that old money feel while enjoying the convenience of a super-short style.
Essentially a buzzcut with longer bangs, the Ivy League style is cut aggressively short on the sides and back and clipped short all the way over the crown. The top blends smoothly from the short crown to an inch or two at the front.
Styling an Ivy League requires little more than a dab of pomade and a comb to create some height at the front.
What to ask for: Tell your barber you’d like an Ivy League buzzed short at the crown and longer at the front.
The Short Layer Cut
As far as haircuts go, the short-layer cut is about as conservative as possible. It’s not too long or too short, but it has just enough length to play with.
A short layer cut is trimmed short with scissors only with enough length to flow back. The hair is cut neatly around the ears and blocked in the back as close to the natural hairline as possible.
Styling the short layer requires only a bit of pomade for shine and control and is brushed back with a wide-tooth comb or brush.
What to ask for: Tell your stylist you’d like a short scissor cut long enough to brush back on the top and sides.
Even if you don’t have old money in your bank account, capturing the old money look is possible.
The overall theme of the old money hairstyle is that it is never too short or too long and can be styled neatly but still looks fabulous even if it is not.
Stay handsome.
