Most guys chasing the “old money look” spend money on clothes. That’s the wrong starting point. The hair comes first. It’s the one thing you can’t buy off a rack, and it’s the first thing anyone notices.
Old money haircut styles have one defining rule: it never looks like you tried. This means clean lines, natural volume, and nothing flashy. The style traces back to Ivy League campuses in the 1920s and ’30s, where Hollywood icons like Cary Grant and Fred Astaire wore sharp side parts and slicked-back cuts that projected precision without effort. That same DNA runs through every cut on this list.
Here’s exactly what those cuts are, who they work for, and how to pull them off.
1. Classic Side Part
The side part is the foundation of the entire old money aesthetic. Hair on top stays 2–4 inches, combed cleanly to one side, with a defined part running from the crown to the temple. Sides are tapered (not faded hard), and just clean.
Jon Hamm’s Don Draper in the AMC television series Mad Men set this as the modern benchmark, while George Clooney’s silver variation proves it ages well. And David Beckham has worn it in at least a dozen iterations without it ever looking dated.
How to Style Classic Side Part
→ Start with damp, towel-dried hair
→ Apply a small amount of pomade or styling cream from roots to ends
→ Use a fine-tooth comb to set the part, starting at the crown
→ Blow-dry the top toward the part using a round brush for volume
→ Finish with a light-hold hairspray if you need it to stay sharp all day
Works best on straight to slightly wavy hair. Medium-to-fine textures hold the part cleanly without looking heavy.
2. Slick Back
The slick back is confidence made visible. Hair goes straight back from the forehead, and the whole shape appears controlled and deliberate. It needs 3–5 inches of clearance on top to work properly.
Leonardo DiCaprio’s slick back in The Great Gatsby is the cleanest modern reference. Michael Douglas as Gordon Gekko in Wall Street is the original. Both rely on the same thing: a medium-hold pomade with just enough shine to look intentional, and not greasy.
However, this cut may fail if you use the wrong styling product. Heavy oil-based pomades will make it look wet and cheap. That’s why here at Fade O’Clock, we use a water-based pomade and comb from forehead to crown in one clean sweep while the hair’s still damp.
3. Ivy League Cut
The Ivy League (sometimes called a Princeton) is essentially a crew cut with just enough length on top (1–2 inches) to create a small quiff or side part. The sides and back are tapered short, around half an inch, and the whole cut keeps a structured outline.
It’s one of the easiest old money cuts to maintain because the short length hides a lot of grow-out. JFK wore it throughout his entire presidency. Ryan Gosling has worn modern versions of it with a slightly longer (or looser) top.
“One thing I really like about the Ivy League style is that it can be quite versatile for a shorter haircut… The top can be combed to the side for a more formal look, the style can be worn with the hair brushed up to resemble a long crewcut, or it can be simply brushed forward as you would a Caesar haircut for the ultimate low style.” – David Alexander, a licensed master stylist, and is recognized in Modern Salon
What to Ask the Barber
Ask the barber for an Ivy League haircut with a textured top. But keep in mind that “Ivy League” may not mean the same thing to every barber, so don’t rely on the name alone.
Bring a photo to clearly show the style you want. This is the most reliable way to avoid confusion. You can also describe it as:
- 1–2 inches at the front, tapered sides to a #2 or #3.
- Slightly longer hair at the front
- Short at the crown with more length toward the front
Even if you say “Ivy League haircut,” always back it up with a visual and simple length instructions.
4. Classic Taper
The taper is what separates a clean cut from an average one. Hair on top stays medium-length, around 3–4 inches, with soft wave or texture, while the sides graduate smoothly from longer at the crown down to the natural hairline.
It’s the most forgiving old-money cut for men with thicker or wavy hair, because the gradual taper controls volume. Pair it with a pomade for a polished finish, or a styling cream if you want it to look more natural.
If you’re in Maple Ridge and want this done right, Fade O’Clock is the go-to barbershop with a reputation for exactly this kind of precision work. One client mentioned that: “I got a low taper… they do a good job… Best place in Ridge by far.” That level of consistency matters when the cut depends on clean blending.
5. Classic Pompadour
The pompadour is the loudest cut on this list. But in the right context, it still qualifies as old money. The hair sweeps up and back off the forehead, which creates height and structure. Short-to-medium sides keep the top as the focal point.
Elvis Presley made the pompadour iconic in the 1950s. David Beckham has worn a lower-volume modern version that looks more refined than retro. The difference between old money and rockabilly is restraint: you want lift, not altitude.
How to Get the Height Without the Stiffness
To achieve the height without stiffness, our Maple Ridge barbers recommend:
→ Blow-dry upward and back while using a round brush at the roots
→ Use texture powder for grip without shine
→ Don’t use gel, as it sets too hard and kills the natural flow
Hair needs to be at least 3 inches on top. Works best on straight or slightly wavy hair; curly hair can work, but requires more product and a stronger brush technique.
6. Comb Over
A comb over is not the kind that hides anything, but it frames your face. The modern comb over keeps 2–4 inches on top, swept cleanly to one side, with tapered or faded sides that create a sharp outline. But you need to know that the styling product makes or breaks it. A medium-hold pomade with a natural finish keeps it looking intentional.
Barber tip: Tell your barber Maple Ridge you want a classic taper with 3–4 inches on top for a side part, and be specific about how short you want the sides. A photo always helps more than a description.
7. Curtain Cut
The curtain cut parts in the middle and lets the hair fall naturally to each side. It’s longer than most cuts here, with 2–4 inches on top, and relies entirely on natural movement rather than structure.
Timothée Chalamet has worn it consistently and made it the reference point for the younger old money aesthetic. The 1990s versions worn by Leonardo DiCaprio and Johnny Depp were looser and longer, while the current interpretation is slightly shorter and cleaner on the sides.
This is one of the few old-money cuts that work without a blow-dryer. Air-dry it, run a small amount of styling cream through the front, and let the part form naturally. Heavy products ruin the whole effect.
8. Classic Quiff
The quiff lifts hair up from the forehead and pushes it back in a soft wave. It’s got more volume than the Ivy League but less structure than the pompadour. Zac Efron’s modern version keeps the texture soft and the sides medium-length, while Chris Pine’s take is sleeker and more polished for formal settings. In short, the quiff adapts well to both. Use moulding paste rather than pomade when styling, as it provides a flexible hold that maintains lift without making the hair stiff or shiny.
9. Bro Flow
The bro flow is medium-length hair (roughly 3–5 inches) that grows out evenly and sweeps back naturally. It looks wealthy-casual the same way a well-cut blazer appears professional without trying.
It’s the most low-maintenance cut on this list, but it still requires clean ends and healthy hair to look right. Without regular trims, it will look like you just haven’t had time for a haircut.
At Fade O’Clock, our clients consistently mention the attention to detail that makes these kinds of natural cuts work. After getting his haircut, one noted, “Best haircut I’ve gotten in a while, attention to detail and cleanliness is on point.”
With this kind of hairstyle, the finish needs to be subtle; you’ll need a good barber to do the cut for best results.
10. French Crop
The French crop is short, around 1–2 inches on top, with a blunt fringe trimmed straight across the forehead and tighter sides. It’s a structured short cut that works especially well for men with finer hair because the blunt fringe adds visual density.
Cillian Murphy’s Peaky Blinders version is the sharpest reference, though that cut leans harder on the contrast between the shaved sides and the longer top. The old money version is more balanced: short but not severe, with texture clay on the top to add definition.
11. Classic Crew Cut
The crew cut is 1/2 to 1 inch on top with tapered sides. It’s clean, short, and requires almost no daily styling. It originated on university crew teams in the 1920s, which is where the old money connection comes from.
Ryan Reynolds regularly wears a standard crew cut. Tom Hardy’s version adds a bit more length on top for a slight texture. But neither needs more than a dab of matte pomade and a comb, right?
So, if you’re going for the old money look without any real maintenance commitment, book an appointment at Fade O’Clock for your classic crew cut.
If you’re still unsure about the best style for you, do not hesitate to ask the barber for the right cut for your face shape.
Book at Fade O'Clock and Achieve the “Old Money” Look
Old money style isn’t about looking rich, but looking like you’ve never had to think too hard about it. These cuts work because they’re rooted in proportion, maintenance, and restraint. Pick the one that suits your hair type, get it done by a barber who cares about the finish, and trim it on schedule. If you’re in Maple Ridge, book your next cut at Fade O’Clock, and expect clean execution and consistent results.
Frequently Asked Questions
Can you get an old money hairstyle if your hair is thinning at the crown?
Yes, thinning at the crown is manageable with the right cut. The French crop and Ivy League both keep the top short enough that crown thinning doesn’t affect the silhouette. For men with mild thinning, a side-part or comb-over style with a bit of texture powder at the roots can create the appearance of density. Avoid slick-backs and pompadours if the thinning is significant, as those cuts pull hair back and expose the scalp. Fade O’Clock barbers specialize in precision cuts and can trim around thinning areas to maintain a clean outline.
How long does hair need to be before you can get an old money haircut?
It depends on the specific cut. The French crop, crew cut, and Ivy League can be done with as little as 1–1.5 inches on top. The classic side part needs at least 2–3 inches. The pompadour, slick back, and bro flow require 3–5 inches to work correctly. If you’re growing out from a buzz cut or short crop, expect 3–4 months before you have enough length for medium-length cuts, and 5–6 months for a slick back or pompadour. An experienced barber can shape the hair during the grow-out phase so it doesn’t look awkward at intermediate lengths.
What's the difference between a taper and a fade in an old-money context?
A taper gradually reduces hair length as it moves down toward the neckline, which blends naturally into the skin over 2–3 inches. A fade removes hair more aggressively, usually reaching skin level higher up on the sides (mid or high). Old money cuts traditionally use tapers because the gradual transition looks more conservative and polished, consistent with the aesthetic’s preference for restraint. High fades, by contrast, create stronger contrast and read as more modern or streetwear-adjacent. If you want the purest old money look, request a taper rather than a fade when you sit down with your barber.
