Introduction: Why You Need to Level Up Your Hair
“I think I’m ready to move past the trendy, flashy styles…”
Have you looked in the mirror lately and felt that way? (Speaking personally, hitting my 30s made this painfully clear.)
There’s a quiet shift happening across all generations, from Gen Z up through established adults: the rise of the “Old Money” style. This look—defined by effortless luxury, class, and refinement—isn’t just about the clothes you wear; the haircut is perhaps the most critical element.
We’re breaking down the Old Money hairstyles and the exact setting techniques you need to make people think you grew up summering in Martha’s Vineyard.
1. Defining the Old Money Look
Photo by Adriaan Greyling on Pexels
In short: It’s timeless, classic, and always clean.
Unlike recent trends like the severe skin fade (where the scalp is visible) or aggressive textured cuts like the twist perm, the Old Money style avoids looking like you’re trying too hard to be fashionable.
Look for these key characteristics:
- Forehead Exposed (Up Bangs): Cleanliness and confidence are paramount.
- Natural Volume on Top: Not puffy, but not slicked flat either.
- Gentle Tapers/Fades: Sides are cut predominantly with scissors, avoiding sharp lines or razor finishes.
- High-Sheen Products: The style relies on natural-looking gloss, not matte clay.
Think of “The Kennedys on holiday,” but updated for 2024.
2. Three Essential Styles to Order at the Barber
Photo by Emre Gokceoglu on Pexels
If you walk into a high-end barbershop, these three styles are the absolute core of the Old Money aesthetic.
① The Classic Side Part
This is the undisputed King of Old Money hair. The key is creating a distinct, deliberate part while allowing the top to have a slight natural flow back. It works flawlessly in a suit but transitions effortlessly to casual wear (think a crisp polo shirt or cashmere sweater).
② The Ivy League Cut
Ideal for men who prefer a shorter, low-maintenance cut. The sides are kept neat and tapered, while the top is left long enough to brush neatly to the side. This cut exudes an intelligent, sporty impression—the quintessential prep school look.
③ The Natural Slick Back
Forget those heavily gelled, helmet-like slick backs of the 1980s. This is a relaxed, hand-raked style, using minimal product to achieve a slightly tousled finish. If you want to convey adult charisma and a sense of effortless cool, this is your choice.
3. The Setting Procedure (Do Not Skip the Prep!)
Photo by Markus Winkler on Pexels
The classic complaint: “It looks great leaving the barber, but it falls flat when I do it myself.”
The truth is, 90% of the Old Money look is built before you touch any finishing product. It all comes down to the blow dryer.
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Saturate the Hair Skip the refresher spray. Wet your hair completely, preferably in the shower, to remove any lingering bed head.
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Pre-Style (Crucial Step!) Spray a generous amount of Sea Salt Spray or a pre-styling tonic throughout your damp hair. This is the secret ingredient that provides natural grit, volume, and texture without the stiff feeling.
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Use the Dryer to Shape Using medium heat and a focused nozzle, blow dry the hair while lifting the roots of the front section. Direct the hair backward or to the side, depending on your chosen style. The hair should look almost complete before you add any pomade.
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Apply the Finishing Product Use a pea-sized amount of Pomade or Hair Grease. Select a product with medium hold and medium to high shine. Rub it evenly on your palms. Apply from the back of your head forward, then rake it backward to ensure uniform coverage.
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Refine with a Comb Finally, use a wide-toothed comb to refine the part and direction of the flow. This final step cleans up the lines and gives you that polished, sophisticated finish.
Summary
Adopting an Old Money haircut instantly upgrades your perceived status. You could be wearing a basic white t-shirt, and people will still assume you have refined taste.
- Expose the forehead for confidence and cleanliness.
- Use the blow dryer to build structure.
- Always use a high-sheen styling product.
Why wait? Ask your barber this weekend for “something more classic and refined.” You might just unlock the ultimate version of yourself.